I received an email recently from a reader who is working with a question that I know is shared by a lot of people – and at its heart, the question is this:

How do I know when it’s time to start following my dream?

This reader has a vision for a business she wants to start, and she is weighing the possibility of starting it now, or pursuing an opportunity to return to the corporate world, where she could sock away some cash for a couple of years and start her business with a bigger financial cushion.

I think all of us can relate to the question on some level – whether we have a dream for a new business, a project, or a big life change, there comes a time when we need to decide when to take the leap into the unknown.

Something about this reader’s question prompted me to think of Elizabeth Crook. Elizabeth is a strategist and advisor to entrepreneurs – I worked with her at my last company – and she is both an incredibly brilliant businesswoman and one of the warmest, most big-hearted people I know. She’s also got a whole website dedicated to “Discovering your yippee,” which is all about finding work you love – so I know she’s been thinking deeply about this question.

So I hopped on a Google Hangout with Elizabeth, and we recorded our chat for you to watch. We share some key questions to ask yourself if you’re facing a similar dilemma, and frameworks you can use to evaluate your options.

(That third thumbnail you see below the video is the fabulous Heidi Hartman, who sat in with us to help us through our first recorded Hangout… obviously we didn’t realize the thumbnails would be shown!)

This is our first time doing this by video (and as you’ll see, it’s a little rough around the edges), so we welcome your feedback. And if you have ideas or questions for next time, please feel free to leave them in the comments, or email me at lb at laurenbacon dot com.

Your turn: How did you know when it was time to follow your dream? I welcome your thoughts in the comments.

Dear New York Times Crosswords marketing team,

As an avid NYT Crossword aficionado, you can probably imagine the delight with which I opened your email with the subject line, “Announcing the Mother’s Day Collection.” The thought sequence sparked by that subject line alone went something like this:

• OMG, imagine if on Mother’s Day, my partner let me stay in bed and do crosswords all morning! That would be heaven.
• How brilliant of the NYT to realize that this is every nerdy mom’s dream!
• How thoughtful and generous of them to send me, a longtime paid subscriber to their iPad app, a little Mother’s Day gift!

See all of those exclamation points? I was that excited.

Then I opened the email, and my anticipation built further. Right there, below the admittedly somewhat odd photo of someone doing a crossword on their iPad (with what looks like a white dude dancing badly in the background), there was a sweet line of text:

We’d like to thank you for being a New York Times Crosswords solver since: 2013-06-04.

Aww! NYT Crosswords marketing team, you rule! I feel so appreciated. And I can’t wait to see my bonus crosswords. What a fun and unexpected way to thank your loyal, paying subscribers.

Obviously, I hit that “Learn More” button immediately. And I was rewarded with… so much disappointment.

The landing page for the NYT Crossword app’s Mother’s Day Collection

I mean, first of all, what is up with that glaring apostrophe in “puzzle’s”? Holy moly. Know your market, people. We are word nerds.

But above and beyond that, I have several beefs with you now.

One: You want me to pay for this? All of a sudden, I feel totally cheated? You led with gratitude – you said “thank you” – and then you followed up with a crass sales pitch.

Mothers don’t give gifts on Mother’s Day; we receive them in thanks for all the stuff we do for you the rest of the year. Come on.

Would you send me a birthday package on my birthday that cost me money? Well, maybe you would, but that’s why you’re going on my blocked senders list.

Two: Where do I even start with the fact that your Mother’s Day collection is comprised of “15 puzzles” (I can’t bring myself to replicate that typo again) “created by women, available exclusively Mother’s Day Weekend”?

OK, it’s cool that you’re featuring women puzzle creators, but why do they get crammed together for Mother’s Day? Are they all mothers? Are “women” and “mothers” equivalent words? (I mean, I know “female rocket scientist” and “maker of the best beef stroganoff” are synonymous to you, but have you learned nothing?)

Couldn’t you make an International Women’s Day puzzle pack instead? Even that would bug me a bit – why should we only be able to buy the women’s puzzles for 2 days, rather than 365 days a year? – but it would at least make more sense. These aren’t motherhood-themed puzzles, or puzzles by mothers, so I just don’t get it.

(Part of me also wonders how much one earns from designing a NYT crossword, and I have to imagine it’s not a particularly lucrative project, which then leads me to wonder if downloading this puzzle pack for $0.99 is just going to make me feel icky about all the underpaid labour these women performed.)

I know what you’re going to say: It wasn’t you; it was the corporate partner who built the app. But they’re representing the New York Times, and they’re doing a poor job of it.

Let’s bring the standards up a bit.

Affectionately yours,

Lauren

P.S. Did I mention I’m a paid subscriber to your app? That’s how much I love you. Please do better next time.

A shout-out to the completely awesome @NYTOnIt for the title inspiration.

I am Lauren, daughter of Barbara, daughter of Eleanor, daughter of Elsie, daughter of Eleanor, daughter of Jane, daughter of Ann.

Years ago, I attended a ceremony to bless a mother-to-be. And the powerful woman who led the ceremony asked us to gather in a circle and introduce ourselves with our matrilineal heritage.

She is of Icelandic descent, and in Iceland, there is a tradition of matronymic naming. I’m sure I don’t need to tell you that isn’t common. Most of us carry our father’s names, and our fathers’ fathers’ fathers’.

As we went around the circle, I saw a few tears as each of us felt the power of naming our grandmothers and calling them into the circle – this circle of women who were assembled to bear witness to a woman at a threshold. The power of acknowledging the women who had borne us.

Have you ever done this? Give it a try. (It might feel awkward. That’s half my point.)

My grandmothers were both named Eleanor. And they lived very, very different lives. Today I’m going to write about my maternal grandmother.

Eleanor MacLeod, nee Darou, was born in May 1925 to a jeweller in Sault Ste Marie, Ontario. She married my grandfather, a farmer of limited means, when she was just nineteen years old; he was eleven years her senior, ruggedly handsome, solid, honest and hardworking. They were deeply in love, so much so that she defied her parents’ wishes and faced down her father’s stormy disapproval to marry the man she’d chosen. Grandpa – Gordon, to her – was her grand romance and he would remain so all her life.

They were playful and flirtatious together. She gave birth to eight children by him (and that’s not counting the pregnancies that ended in miscarriages). She moved away from the comforts of the city, to a tough, farmer’s life with no electricity, indoor plumbing, or nearby neighbours to whom she could turn for socializing. (She’d been very outgoing back home, and craved company.) And she, the only girl in a family of boys who’d all gone to university, chose a life with very limited options for intellectual stimulation. She wrote a social column for the weekly community paper, which catalogued the quotidian lives of its readers: So-and-so’s daughter had given birth to a healthy baby boy in Sudbury, or such-and-such’s son had been up to visit from Toronto.

I remember her quilting, her throaty, earthy laugh, and her temper.

She was prickly, my grandma MacLeod. Not the bosomy, sweet grandmother of picture books. She was quick to kick us all out of the house and into the surrounding fields when she was sick of our childish noise. (“Go on and let the stink blow off!” she’d yell.) She tore around the house like a drill sergeant, hollering commands to her army of children and grandchildren. And she was quick to judge anybody who didn’t see the world the way she did.

She was a terrifying presence at the card table, as well.

To be honest, my grandfather was a far easier person to feel close to. Grandma always seemed harried, and a little crotchety. But she had her moments of greatness.

I loved the way she was with my grandfather. She showed me what lifelong romance looked like. The way her eyes sparkled when they landed on him. The way she’d say, “Oh, Gordon,” when he made her feel special. (I imagine she sounded exactly like that at eighteen and nineteen, sneaking off to go to a dance with him.)

I loved her frank appreciation of sex. (No matter how modest you are, you can’t live on a farm without encountering sex as a basic fact of life on a near-daily basis.) My grandpa gave her a new set of bedroom furniture for their anniversary one year, and he must have been in his seventies, but it was clear by the way their eyes danced over the bed frame that the two of them had plans for it. My mother remembers her mom volunteering to take all the girls in the community to the city to see Blue Suede Shoes, the Elvis movie none of the other mothers approved of because of his wild hips. And one of my favourite memories of grandma is watching her unveil a gag gift she’d made for one of her sons-in-law, a master of lewd and crass humour who also enjoyed cooking: She’d quilted him an apron with a pleat down the middle that hid a lovingly hand-quilted cock and balls. (Yes, really.) I don’t know who laughed harder, the giver or the recipient. But I knew that day that I’d come by my sense of humour honestly.

And while she was conservative and very set in her ways, she had a profound pragmatism that always won the day – so when my mom told her that the reason she and my father were divorcing was that my father was gay, Grandma’s response, after a brief pause, was, “Well, I guess we have to just accept it and move on.” No wallowing in moralism or self-righteousness, there.

She was demanding, and sometimes slightly surreal in her inability to do things that any other farmer’s wife would consider essential. She was a terrible cook, an even worse money manager, and loathed housework. We had an epiphany once and asked her if she’d had servants growing up. “Of course,” she answered lightly. It explained so much that we’d never understood previously. No wonder she didn’t know how to cook or clean – other people had always done it for her. Yet she chose a life where she had no helpers apart from her husband and children. Needless to say, her kids remember her as a bit of a tyrant.

She was also bipolar, and had terrible lows and highs, both horrible in their own ways. She was on meds most of my life, but went off them occasionally and would fight hard against going back on them.

My grandmother MacLeod taught me a lot.

She taught me that love really can conquer all. She sacrificed a lot to be with my grandfather, and I never once heard her frame it that way. She’d chosen the love of her life, and that meant everything to her. The little things – education, career, money, the comforts of home – shrunk in importance.

In her unwavering pragmatism, she taught me that when in doubt, it’s best to begin by putting one foot in front of the other.

She taught me that all of us have a right to pleasure, carnal and otherwise.

She went her own way and didn’t give much of a hoot what other people thought of her.

She also modeled for me some things I didn’t want for myself:

While her love story with my grandfather was very romantic, I thank heaven every day that I never had to make choices like hers. The day I learned that her father forbade her to go to university, even though all of her brothers had gone, I learned a lot about what a difference fifty years can make. I often wonder whether she’d have been happier and easier to love if she’d had more options in life.

She never let us get close to her, emotionally. I wish I’d seen her open and receptive once in a while. Observing her whirlwind of constant activity and frequent criticism of her family was a good reminder to lead with love and listening.

As she aged, she grew more and more lonely, because her friends were dying and she pushed prospective new friends away. While I sympathize deeply with her grief for her lost friends, I know that her latter years were far more isolated than they had to be, because of her refusal to accept newcomers into her circle.

There’s a moment I’ll always remember. I was back on the family farm for a visit; I was in my early twenties, pursuing a music degree, and I remember feeling like my everyday life was so far removed from life on the farm that it felt nearly impossible to bridge the two. I knew my grandmother had no real way to wrap her head around the life I’d chosen, from its deep city-centricity (if that’s a word) to the highbrow culture I’d chosen to immerse myself in. I had found it difficult to connect with my grandparents on this trip, because I didn’t know how to communicate what I did in terms they’d understand, and I knew it must be obvious to them that their world was equally foreign to me. My mother had been the only one of her siblings to move away, and I felt like I had compounded that distance by not only living across the country, but in a different world.

I was getting ready to leave, standing in the driveway in front of the small, one-story farmhouse, after packing my bags into the trunk of the car. I turned back to my grandma and grandpa, and they hugged me goodbye. And Grandma leaned forward and tucked several folded bills into my pocket, wordlessly.

They didn’t have money.

They had twenty grandchildren.

And they were giving me a hundred dollars.

I gave her a look. Come on, Grandma. I can’t take this.

“I don’t get to buy you all the things I buy for the other kids,” she said, with wet eyes. Meaning the kids who’d stayed close to the farm.

I thought about what I’d buy with it. Certainly nothing she’d choose for me. Maybe some CDs or sheet music. Maybe some more black, gloomy clothes. She didn’t mind what I did with it. She wanted me to have something she wouldn’t pick out.

“Thank you.”

It was too much, and it was sweet, and it was as sentimental as my grandma ever got with me. And that’s just fine by me.

This post was inspired by Tara Sophia Mohr’s Grandmother Power blog campaign. I hope you’ll consider participating as well.

Last night, I had the pleasure of speaking to the Vancouver User Experience group (AKA VanUE). The theme was “Inspiration,” so I decided to focus on something that’s preoccupied me for my entire career in tech, which is how we can bring our best selves to technology, and use technology in ways that help us grow and evolve in meaningful ways.

I titled my talk “Fitter, Happier, More Productive: How Tech Can Help Us Be & Do Better.” I talk about:

• Why motivation matters less than you think.
• The 3 factors you must have in place in order to shift your behaviour, according to Stanford professor BJ Fogg’s amazing research on behaviour design.
• My rebuttal to venture capitalist Tim Chang’s “7 Deadly Sins” framework for assessing how successful an app is going to be.
• Three apps that have made me a better, happier, more thoughtful person.

I’ve uploaded my slides to Slideshare with an audio track. (Warning: the slides make very little sense without the audio, because I’m a firm believer in using slides for illustration and counterpoint only.)

How do you think technology can help people be and do better? I welcome your thoughts in the comments.

A thoughtful reader recently asked about the role of male allies in solving the gender imbalance in the tech industry:

As a guy in the tech industry, I honestly don’t know how to fix most of the issues… I do want to help, but like many other guys I don’t know the best way to do it. I recognize and accept that there are biases and barriers in our industry, but I don’t on know what can be done.

This is quite a common question, and I’ve attended several conference panels on the subject – though I confess that after a bit of googling, I’m not finding much on the subject in writing. (Anyone have links they’d like to share?) Of course, it’s not only a question of what men can do, but rather what everyone can do to make a dent in a huge, systemic problem.

My take on this is that the best approach depends on your position, ie what you have the power to do, and on what sort of stuff comes most easily to you. There isn’t one thing you need to do, any more than there is one way you can solve climate change or stop people from behaving badly on public transit.

But in the interest of giving you more actionable advice than, “It depends,” here are some thoughts.

If you’re a conference organizer:

• Read these posts: Increasing Diversity at Your Conference, by Ashe Dryden (amazing roundup of resources – if you read just one, make it this one); Solving the Pipeline Problem, by Sarah Milstein and Eric Ries; and How to Ensure Speakers Diversity at Your Conference, by Julius Solaris.
• Get as much diversity as you can on your selection committee.
• Actively brainstorm lists of women, people of colour, GLBTQ folks, etc. who you could invite to speak and attend. Reach out to them individually. Understand that they may need more active encouragement and coaching during the submission process. Make it easy for them to propose talks, and let them know their perspectives are wanted.
• If you’ve had a lack of diversity at the podium in the past, or harassment/safety issues, step forward and admit it – and make a public pledge to do better. We don’t need you to be sorry, but we do need you to make it clear that you’re aware of the problem and actively working on it. Invite input into what you can do differently this time.
• Adopt an anti-harassment policy (more here), and make good on it.
• Do a post-mortem analysis of what worked and what didn’t. Write it up as a blog post, speak about it where you can, and help others learn from your experience.

If you’re an employer:

• Check out what Etsy has been up to in their successful efforts to recruit more women engineers.
• While you’re doing your research, here’s Google’s approach to hiring and retaining women employees.
• If your team is currently all-male (or if your only women employees are in non-technical roles), recognize that many women won’t apply for a job with you until they feel confident that it is a welcoming environment. Yes, this means that recruiting your first female, technical employee could be extra challenging. So you will need to comb through your address book, ask everyone you know for referrals, and dig deep to find promising candidates – and then actively encourage them to apply.
• It never hurts to put language in your job postings that explicitly states that women, people of colour, and GLBT candidates are encouraged to apply.
• As with conferences that have had harassment incidents in the past, some workplaces have a reputation as “brogrammer” hangouts. If that’s the case for your company, consider making a public statement (like this one from Klout) to let women and trans people know that you are working to change your stripes.
• Check your job postings for gendered or exclusionary language: Yes, this means dropping “ninja” from job titles.
• Review your hiring process with an eye to making it gender-blind. Again, I’d look at Etsy’s evolution here; they’ve dropped changed their approach to technical interviews for some of their recruits [edited after reading Martha's comment below], acknowledging that the technical interview is largely done in deference to tradition (CTO Kellan Elliot-McCrae describes the standard coding-at-a-whiteboard test as “Prove to me you’re smart”), rather than because it’s actually effective.

If you manage or lead a team:

• Consider providing coaching or mentoring to female employees to build confidence and leadership skills – either yourself or by bringing in outside expertise. Many successful women, especially the pioneers who blazed trails in formerly unwelcoming industries, credit male mentors for giving them opportunities to advance and grow.
• Actively encourage women to apply for raises, promotions, and recognition – research shows that women are more reluctant to ask for them (and that even when they ask, they receive less) and it has an adverse effect on their lifetime earnings and status.
• Ask for feedback on what you could be doing differently to make the workplace better for your female employees. If possible, make it easy for them to submit feedback anonymously.
• Ask the women on your team to help you recruit more women.

If you’re an investor:

• Read up in the stats about women’s lack of VC funding, versus their average profitability and success rates.
• (Other ideas? I confess I’m a bit out of my depth on this one.)

Things everyone can do:

• Keep reading and listening to women’s voices in the industry. We all have different perspectives (which is kind of the point), and we ain’t going nowhere if we don’t have men working alongside us to change the ratio.
• Watch for sexist or exclusionary behaviour in yourself and your team members, and call it out when you see it. That includes everything from ditching bikini-babe desktop wallpaper to subtler things like paying attention to who talks more (and is listened to) in meetings. Pay attention and practice saying, “Hey, I know you probably didn’t mean to do this, but I noticed [offensive behaviour] and here is the impact it is having on me.”
• Talk to girls about what technical work looks like. Share your enthusiasm for what you do with kids, and explain how it feels to make cool stuff with code. Offer to teach them if they’re intrested. Consider visiting a school to share your skills or talk about your work. Focus your attention on the girls and invite them to ask questions.
• Got skills, cash, or connections? Offer to teach a class for Girls Who Code, Girls Learning Code, Ladies Learning Code, Hackbright Academy, or one of these other groups – and while you’re at it, promote their courses to the girls and women in your life, and/or contribute to a scholarship fund.
• Write a blog post about why gender balance in tech matters to you.
• Check out this awesome Dad’s hack of Donkey Kong. How can you hack something for your daughter (or someone else’s) to make it work better for her?
• Celebrate Ada Lovelace Day, and write or speak about the women in tech who inspire you.
• Follow some techie women on Twitter. Listen and engage. Keep learning.
• If you’re invited to speak on a panel, ask who the other panelists are. If they’re all men, recommend a woman who could take your place. (Or consider taking the pledge proposed by Rebecca Rosen in The Atlantic a couple of months ago.)
• Advocate for decent parental leave and work-life balance policies in your workplace.

I realize this is a long post already, but I know it’s woefully incomplete. Ideas on how to improve it? Please leave your thoughts in the comments.

One of the real challenges of diversifying your team is that – at the risk of stating the obvious – your workplace is going to feel different, because it will include more difference. And that’s not always a comfortable feeling.

I see small companies struggle with this all the time. For a small team, every new hire risks being disruptive, and if you branch out from your demographic norms, whatever those are (age-wise, ethnicity-wise, gender-wise, ability-wise, and so on), that can feel higher risk.

When we feel uncomfortable with a prospective new hire, it can be easy to fall back on “culture fit” as an excuse for sticking with same-same demographics. And I’m not talking here about overt bigotry – I’m talking about its subtler cousin, cognitive bias. It’s easy to fall into the trap of wondering whether someone who doesn’t fit the usual profile is going to fit in, be it because they’re an immigrant with an accent, significantly older or younger than the rest of the team, a woman of colour, seemingly oblivious to your sense of humour, or otherwise different from the other folks on your team.

The key distinction here is between culture and values. You don’t need people to fit your culture – but you do need them to reflect your values.

Culture Is Less Intentional Than You Think… So Stop Holding It Sacred.

Your organizational culture is a bit like your personality: You may have honed some aspects of it, but you didn’t choose it consciously. As Shanley Kane brilliantly put it:

Culture is about power dynamics, unspoken priorities and beliefs, mythologies, conflicts, enforcement of social norms, creation of in/out groups and distribution of wealth and control inside companies. Culture is usually ugly. It is as much about the inevitable brokenness and dysfunction of teams as it is about their accomplishments.

I don’t know if I’d go so far as to say that culture is usually ugly, but it certainly can be, and it’s a leader’s job to be mindful of what culture we create and how it can become better, more inclusive, and more conducive to doing excellent work.

And while Kane rightly points out that much of culture is unconscious, that isn’t to say you shouldn’t work on defining and nurturing the culture you want your company to embody; it’s simply to recognize that “culture” demands conscious (and conscientious) choices on your part, or it will become a force for exclusion.

Here’s my suggestion: Stop worrying about your corporate culture and focus on your company’s values.

I know, I know: Lots of companies have vacuous “vision and values” statements that suck. Your values can, and should, be vital. They should be communicated to every employee before they’re hired, instilled into every key decision-making process, and discussed often. They should be living words that you wrestle with.

How To Have Organizational Values That Actually Mean Something

When I was at Raised Eyebrow, for example, one of our core values was, “We praise each other.” (We had several others that focused on honesty, continual learning, sharing knowledge, empowering our clients, and so on.) Praising each other looked different for every team member: Some did it by speaking directly to a teammate (we provided sheets of gold star stickers for everyone to hand out as recognition of each other’s accomplishments), others by speaking up in team meetings to make sure everyone knew how a colleague had contributed to a success, and managers were tasked with bringing that value to performance evaluations.

Every month, we held an all-hands meeting that consisted in part of reviewing each of our values, and engaging with it – how were we doing with embodying this value? Where were we falling down? What were some examples where we’d seen this value in action? What were some missed opportunities?

We spent a lot of time on this, because we learned that focusing on our values created room for raising difficult subjects – and it also helped us all focus on the big picture and realign to our highest aspirations as a business. When we discussed our values, we brought our biggest and best selves to the table, and checked our egos in favour of the greater good.

That may sound lofty, but isn’t that what you want? Employees who are fired up about doing their very best work?

A values focus is the best way to nurture intrinsic motivation that I know of.

We took our values focus and applied it everywhere we could. Performance reviews incorporated our values, as did our process for choosing clients and projects. If a client wasn’t a values fit, we said no.

Destroying the Status Quo (Because the Status is not Quo¹)

Values are something you can hire for; they’re something you can evaluate staff on; and they should be things that any employee can work towards embodying, without compromising who they are. (Even shy and reserved team members can usually handle a quick “Good job” and a gold star.)

Culture fit matters only insofar as it translates as “values fit.” If “culture fit” is code for “looks like us and talks like us,” it’s a problem for you and your business, because you are sending a message to many prospective employees that they are not welcome – and depriving your business of the many benefits of a diverse team.

Try this: list out the qualities you think constitute your company’s culture.

• What makes your workplace stand out from the crowd?
• How does it feel to work where you work?
• What are the unspoken rules of working there? (For example: Do you have an espresso machine in the kitchen? You may expect your colleagues to be high-energy and have sophisticated taste.)
• How would you describe a typical day at the office, in ten words or less?

Now ask yourself these questions, to discern the difference between your culture and your values:

• Ten years from now, what impact would you like your company to have in order to feel like your work has had meaning?
• How would you like it to feel to work where you work?
• How would you describe an ideal day at the office, in ten words or less?
• What qualities could your workplace espouse more deeply in order to be an even better place to work?

Culture is the status quo; values are the standards you hold yourself to.

And once you’re focused on your values rather than maintaining the status quo, you’ll find there’s a lot more room at the table for a diverse team – without compromising on sharing the common ground that matters most.

This piece originally appeared on Quartz, but I’m quite proud of it, so I’m republishing it here.

I’ve had it with meritocracy.

Not because it’s not a wonderful concept. Of course it is.

My problem is with the belief many people seem to hold that the world (or some part of it) is already a meritocracy, or even that it’s an achievable and realistic ideal, rather than a platonic one. This mythology is particularly rampant in the tech sector, perhaps because coders deal so much in the cold logic of zeros and ones that they imagine their professional lives are exempted from any kind of bias. It’s been my experience that quite often, any suggestion that the sector lacks diversity is perceived as an attack on the concept that people should be hired, promoted and celebrated for their skill rather than their demographics.

I can count at least three instances in the past week where an online conversation about gender diversity in tech was rapidly hijacked by someone arguing that diversification strategies were bound to dilute the caliber of [fill in the blank]: conference speakers in one case, technical employees in another, “focus” in a third.

Just about every time diversity comes up in tech-sector conversations, there is a chorus of protests that tech is a meritocracy where anyone who’s talented and hardworking will advance smoothly and quickly. The problem with that belief system is that it assumes that there are no external or internal forces contributing to some groups being underrepresented in tech. I would argue that there are both.

While it’s a wonderful and important ideal, “meritocratic” is a long way from being an accurate description of our current state of affairs, thanks to human foibles of various kinds. Those foibles can be broken down roughly into two types: biases (both conscious and unconscious) that limit people with qualifications from advancing, and barriers (personal, social, and systemic) that prevent people from attaining the qualifications, support, and mentorship necessary to succeed.

Let’s talk first about biases. (I’m going to focus here on gender diversity, but some of these suggestions play out in similar ways around race, ability, sexual orientation, and other kinds of difference.) I see some of the resistance to gender diversification efforts in tech stemming from a conflation of conscious and unconscious bias—that is, a belief that because overt sexism, racism, and other forms of discrimination have been expunged from your vocabulary, that you’re therefore incapable of sexism or racism.

Here’s the thing: The defining feature of a blind spot is that we don’t know it’s there. And it’s hard to notice it until we’re challenged on it. We see this again and again with all-male speaker lineups at tech conferences. I certainly don’t believe the organizers of those conferences are rabid misogynists; they just have a blind spot when it comes to gender, and frequently don’t notice the lack of women until it’s pointed out to them.

I don’t think most of them have contemplated the possibility of cognitive (i.e. unconscious) bias. Uncomfortable though it may seem, it’s incumbent upon those in positions of power to familiarize themselves with the concept of in-group bias, and figure out ways to correct for it. Several conference organizers have blogged recently about the strategies they’ve used to improve speaker diversity, and one of the recurring themes is that it takes real effort to break out of the default mode of inviting people like ourselves, but that the conscious effort of reaching beyond the usual subjects has improved both the diversity and quality of their speaker lineups.

Lest the conference organizers think I’m putting all the responsibility on them for those all-male speaker lineups (and let me just reiterate that I’m not just talking about conferences here—this applies to hiring, promotions, compensation, status—in short, all the ways we rank people professionally), there’s a whole other side to this, which is the stuff that prevents women, non-white people, and other marginalized groups from entering into “meritocratic” competitions in the first place.

First, as we all know, there is a pipeline problem in tech. The pipeline problem has many roots. For starters, there is an acknowledged achievement gap between girls and boys in math and sciences, and while we can debate until the cows come home whether that’s a nature thing or a nurture thing, it means gender and race discrepancies in STEM can start as early as primary school. Unsurprisingly, further up the education ladder, we see fewer women completing STEM degrees or even beginning them in the first place.

We also know that there are socio-cultural aspects to this stuff. Girls are frequently dissuaded, whether by family members or peers, from pursuing solitary, geeky pursuits like computer coding. They also don’t see a lot of role models they can look up to.

The result is that there’s a pretty massive gender divide in the tech sector, with a roughly 75/25 male-female split and worse numbers in university computing programs, with just 19 women in every 100 graduating computer science students last year. Some data suggest the ratio of men to women in the tech industry gets more out-of-whack the more techie the role, though it’s harder to get hold of substantial data on that front, with no thanks to stonewalling by some of Silicon Valley’s biggest players.

Some critics of diversification efforts will be tempted to point to these numbers and suggest they constitute the whole story: fewer women enter the ring, so of course there are fewer winners. But let’s jump ahead and assume you’re one of the women who made it through the first round of hurdles: you’re a computer geek with a university degree, and you’ve found yourself a job. I hate to break it to you, but you’re facing another set of challenges, and this time, they’re internal.

Women are less likely to put themselves forward for advancement opportunities such as VC funding, promotions and raises, speaking engagements, and so on. Those who have delved into this problem have discovered that the reluctance can be overcome with mentorship, coaching, and encouragement from peers, but many women seem to be plagued by self-doubt, impostor syndrome, and fear of failure that means many of them self-select out of competition.

Similarly, there is some evidence that women don’t apply for jobs unless they feel 100% qualified, while their male counterparts consider themselves strong candidates even if they lack a qualification or two.

One of the challenges of the debate on tech sector diversity is that both proponents and detractors of diversity have a tendency to focus on a single axis of the problem: Bias or barriers. And as we’ve seen with the recent critiques of Sheryl Sandberg’sLean In, it’s all too easy to derail a discussion about one (in this case, barriers, since Sandberg’s focus is squarely on the internal hurdles women face) with criticism that the other (systemic bias) has been unduly ignored, and that the discussion, therefore, has no merit.

I’m of the opinion that until we embrace a “both, and” mentality about this stuff, there’s a limit to what we can accomplish. Women face internal barriers, yes, but we don’t do so in a vacuum. And while bias is an unavoidable fact of life for individuals and the organizations we build, we do ourselves no favors by foisting all the responsibility for change onto others.

If we can agree that cognitive bias and internal barriers exist in the tech world (and I really, really hope that we can, because there’s plenty of evidence to support their existence), then we can begin to acknowledge the sometimes painful reality that we do not work in a pure meritocracy. That, in turn, will allow us to work creatively on strategies to help us to build systems that more closely resemble the merit-driven tech culture we so passionately want to see.

A note about this post: None of what follows is a legal opinion; I’m not a lawyer, and I haven’t run this past a lawyer to see whether I’ve held to the letter of the law in my recommendations. I recommend you consult legal advice before terminating any employee, whether for cause or otherwise. My intent here is to spark discussion on how to make terminations more human and humane. I welcome comments and feedback – especially from those better versed in legalities than I am.

“There’s no easy way to say this, so I’ll cut to the chase,” I said. “This isn’t working out.”

He nodded his head, looking me in the eye. “Yeah,” he said, after a pause. “I don’t feel like you’ve seen my best work.”

“I agree. And I believe you’re capable of so much more. But for whatever reason, this doesn’t seem to be the right place for you.”

The conversation continued for some time after that, unstrained, though tinged with sadness. In fact, I think we chatted for a good twenty minutes or so, friendly to the last. I really, really liked this person; still like him, in fact, and look forward to running into him at local tech meetups and other geeky events. He’s brilliant, funny, and my kind of quirky. But he wasn’t a fit for my business.

This goes down in my personal history as the least stressful dismissal I’ve ever had to make. But while it’s not something most people relish, I’ve come to feel at peace with firing people when it’s necessary.

That’s not to say I look forward to it. I can’t eat a bite beforehand, and I don’t sleep very well the night before. I feel terrible before and during, and I don’t do it lightly. But I’ve learned a few things that make it much easier – and more importantly, that I think convey the kind of kindness and respect that belong in any employer-employee conversation.

Before I dive in, it’s worth noting that I’m not talking here about firing an employee who has done something that violates your company’s ethics, or the law. That’s an entirely different matter. I’m talking about firing someone who just isn’t an A player, when you need an all-star team – someone you like and respect, but have come to realize isn’t bringing you the results you need.

That person deserves a compassionate, respectful dismissal. So how do you do that? Some thoughts:

• Frame it as a poor fit. What you are about to do is sort of the opposite of a sales pitch: Instead of seeking a good fit between needs and offerings, you’re here to explain why their particular gifts are not a match for what your organization needs. It’s not about them being a bad person, or incompetent (even if they seem that way to you); it’s that they don’t bring the capacities you most need at this time. You can respect their gifts all you want, but if they aren’t right for your business, it’s time for them to take them elsewhere. While you may harbour a strong desire to list out all their most aggravating flaws, it is probably not their unwillingness to take their food out of the staff fridge on weekends that has led you to this point. Focus on the big picture: Your needs are X; their strengths are Y; and they’re not matching up.
• Edit your script. Once you’ve reached a decision to let someone go, it’s not helpful to catalogue every challenge you’ve had with them in the past. Nor is it worthwhile to sugar-coat everything you say, because the fact is, they won’t remember the nice things you’ve said when the outcome is that they’ve lost their job. My preferred middle way is to lay out a couple of relevant observations (“The company needs _______ right now, and that doesn’t seem to be your strong suit”; “We’ve made several attempts to get you up to speed on ______, but we’re not seeing the progress we’d hoped for”), explain how you arrived at your decision, and infuse the whole thing with kindness by letting them know that you’re sincerely sorry it hasn’t worked out.
• Consider what you can offer them to cushion the impact. I always prefer to offer a generous severance package, and if I’m able, a letter of reference for future employers. I would far rather pay someone out than have them keep working incompetently. And I would rather give them a financial cushion to help tide them over until they find another job. If you can’t write a reference letter without holding your nose, though, don’t offer one. Better to abstain than to compromise your integrity, or deliver a lukewarm testimonial that damns with faint praise.
• Practise what you’re going to say. You will be nervous – as nervous as if you were giving a speech to a huge crowd. Rehearse your talking points as if you were going on national television. This is a good place to put the anxious, night-before energy, since odds are you’ll be rehearsing inside your head anyway. If possible, find a trustworthy companion to practise with.

The Dreaded Conversation

The conversation itself doesn’t need to be torturous, either. But it does require forethought. I try to follow this routine:

• Do it early in the day. There are several reasons for this, beginning with the fact that you won’t be able to focus on anything else until it’s over with. So get it done, and you can both move on. Also, there’s no point delaying a fire once you’ve made the decision. Any work they’re doing can and should be passed off to someone else ASAP, because you’ve already established that you don’t have faith in their skills.
• Do it face to face. If you’re on a virtual team, this may mean you have to travel to do it. So be it. Anything else is pretty much the equivalent of breaking up with a significant other via text message.
• Cut to the chase. This is not a time for asking questions, giving a ton of background detail, or rambling. There is no preamble that will soften the blow – and once the blow has been dealt, there’s not much more to say. (Not only that, but the more you say, the more room you leave for confusion.) Asking them for input along the way sends mixed messages, because this issue is not up for discussion. I usually acknowledge that what I’m about to say is difficult, and then spit it out.
• Breathe. Give it a moment to sink in. Let them ask questions if they have any. (Once you’ve delivered the news, they may have clarifying questions. Give them a chance to ask them, and to share any immediate reaction they have, even if it’s an emotional outburst. Try to respond with equanimity, and resist the urge to bring out your laundry list of grievances. Stick to your talking points.)
• Explain what happens next. They will likely be in a state of shock, so it’s helpful to guide them through the next few steps. You might need them to return any company property (like project documents, etc.) they have in their possession. You most likely need keys, fobs, and/or pass cards returned. Let them know what their final paycheque will look like, and when they can expect to receive it – along with any government paperwork. If they have medical and dental benefits, explain what happens with those.
• Give them the option to say goodbye. Some will be too upset to want to talk to anyone, and will just want to get out the door as quickly as possible. Others will appreciate the opportunity to say goodbye to their colleagues. (They may frame things more ambiguously, suggesting they quit, to save face – let them. You can set the record straight once they’re gone.)
• Offer them a ride home. Ask if they’d like you to call a cab – and foot the bill. Or maybe they’d like a friend (or significant other) to come pick them up. Make sure they’ve got a safe way to get home, ideally with some company. (It should go without saying, but just to be clear: I’m not suggesting you actually drive them home.)
  
• Once they’ve left, share the news with your team. Try to plan for this, by giving yourself time in the day’s schedule to notify the rest of your staff. In a smaller company, ideally this happens at an all-hands meeting so you can tell everyone at once, face to face. (In larger ones, it’s probably not of concern to all staff, so use your judgment on who needs to know.) Explain in broad brushstrokes how you arrived at your decision, so that it’s clear to them what happened – but refrain from sharing any details. This is a good time to reprise your “poor fit” explanation. You don’t need to justify yourself, though you may feel inclined to; odds are, they were as aware as you are of the mismatch, so while they may feel some shock on an emotional level, they will likely understand the business sense in the decision. It’s also important to maintain consistency, as it’s likely that some of them will maintain friendships with the departed employee, and they will hear his/her side of the story. Let them know you’re available to field questions privately if they have any. Now is also a great time to reassure them that they are appreciated and that you’re not embarking on a round of layoffs (assuming those things are true) – as the news will likely make them a little nervous about their job stability.
• Breathe some more. Feel that butterfly of liberation unfolding its wings in your belly? That’s a sign you just did the right thing. Now go talk to the rest of your team, change any top-secret passwords, and then go for a walk or something to work the adrenaline off.

A couple of things to remember:

• Yes, this experience will suck, for both of you. But what sucks more is to continue paying someone a salary when you know in your heart of hearts they are not contributing high value to your company. And frankly, it sucks for them to work for someone who doesn’t appreciate them. This is a rip-the-bandaid-off moment: It stings at first, mightily, and then the relief floods in. (Maybe even, eventually, for the person you fired – let’s hope they find a better home for their skills and passions.)
• The old adage, “Hire slowly; fire quickly” is excellent advice. Once you catch yourself fantasizing about one of your employees quitting their job, or imagining how much more you could do with someone else in their place, it’s time to seriously consider dismissal. Take it from someone who’s let things drag out: Do not let things drag out. It only makes things worse in the end, because it means you’ve invested more time and energy in the relationship, and so have they, and ending it becomes that much tougher.

There’s no way around it: Firing someone is profoundly unpleasant. But it doesn’t have to be unkind, and the scars can be mitigated by ensuring the process is as human as possible. The key message should be, “This job is not a fit for you” – so that dignity and mutual respect can remain intact.

Yesterday, I spoke at Ubizo, a conference for small business owners workshopping business challenges with peers and mentors. This is the written version of the talk I gave, which is a little different than the version I actually gave. I was asked to speak about a challenge I overcame in my entrepreneur’s journey. It’s about discerning when it’s time to go with the flow, and when it’s time to push yourself to do things differently. And about the biggest turning point in my business and my career.

I discovered coding by accident. I was in university & I started doing it in my spare time, learning it from a roommate. I just thought it was fun. I started building websites, designing things in Photoshop. We were collaborating on websites just for the fun of it.

Meanwhile, in my “on purpose” life, I was going to grad school, trying to make something out of the music degree I had completed a year earlier – trying to turn it into a “real career,” because I didn’t want those 4 years of university to go to waste. I was horrified at the prospect of admitting that those 4 years had been spent doing something that wasn’t going to turn into a full-time profession, even though I knew that I wasn’t cut out for a career as a musician. My rational mind wouldn’t let me admit that music was not in the cards for me, and that my undergraduate education didn’t really matter that much.

I dropped out of grad school by accident. Because I took this day job coding for my friend, who had now started his own company. I moved back to Vancouver. I told my thesis supervisor I’d be working on my thesis in my spare time, and I figured this was just a nice way to earn some money and pass the time while I figured out what I really wanted to do with my life.

I fell in love with web design by accident. And I dropped out of grad school to focus on my work, which had become my passion.

I started my own company by accident. I was out for a walk with one of my coworkers, who had become a very close friend. We were talking about what we liked and didn’t like about the company we were working for, and how it was growing a little faster than we’d like. And we were having trouble keeping up with the constant shifts in the workplace. We longed for the personal touch that we used to be able to give to each of our clients. And without thinking, I blurted out, “You know, we could start our own company and this could all be different.” And our eyes met, and I blushed, knowing I couldn’t take it back, I couldn’t un-think the thought. And Raised Eyebrow Web Studio was born. Two months later, we left our jobs, set up desks in the corner of my bedroom, and got to work building something new.

This whole going-with-the-flow, living-life-by-accident thing was working pretty well so far.

But then about three years in, we found ourselves stressed beyond belief. We’d been struggling against our own success. We got very, very busy. One of the principles we had started our company on was that we wanted to work a regular 9-to-5 schedule. The tech industry is infamous for long hours, so we had gotten used to an overtime culture, but we didn’t like it and we wanted something different. So we had set as one of our core measures of success that we didn’t want to work weekends, that we wanted our evenings to ourselves. And yet, we found ourselves 3 years in, compromising on the kind of success we wanted.

Everyone we spoke to told us it was time to hire some help. We resisted.

We resisted for all kinds of reasons, which I’ll get to in a minute. And the fact was, our resistance wasn’t rational, and it wasn’t good for our business – or for us. So, finally, after two years of battling this exhaustion, at the 5 year mark of our business, we gave in and hired someone part-time, 20 hours a week, on a 3-month contract, to code.

Once we made that change, it changed EVERYTHING.

This was a big turning point – not just in my business, but for me. Because what happened was, the guy we hired to code for 20 hours a week for 3 months turned our business around.

He made freedom achievable again. He was a delightful human being. He was a better coder than I could ever hope to be – because I was too distracted by all of the other things I was doing, like designing all of the websites we created, and running the business – and because he was able to do nothing but code, he was way more efficient than I was. And I got to focus on the stuff I did best, and he made the company more profitable. Our cash flow improved, because we were able to turn around projects that much faster, and invoice more quickly. Our profitability improved, because we were able to charge him out at a higher price per hour than we paid him. And stress started to leave our bodies. There were all kinds of great business reasons to do this.

So at this point, you’re probably thinking that I’m trying to sell you on the value of hiring staff – but that’s not where I’m going with this. I don’t think everyone needs to hire staff. Your path is your own and maybe it involves staff, and maybe it doesn’t. But the big lesson is this: When you are overwhelmed, overworked, and overinvested in maintaining the status quo – when you find yourself resisting change even though what you’re doing right now isn’t really working – that is a sign you are not fully in charge of your life. You are letting things happen to you by accident. I have been in that place, and it’s not fruitful.

The juicy part of this story isn’t the happy ending of how hiring staff saved the day. It’s what took place in those two years between the point where I hit overload, and the point when I finally hired someone.

Something shifted in me – something had to shift, in order for me to step into the boss role. To be not just the boss of me, but someone else’s boss. It took me nearly two years to wrap my head around it, because it was a huge inner transformation. This was big, heart-and-mind stuff – the kind of stuff we don’t get comfortable with overnight.

I had to do 3 things:

First, I had to give myself permission to change my mind about how I wanted to run my business.

Up until that point, we had a cozy little 2-person friends-and-coworkers vibe. We had a ton of flexibility, both of us collaborated on every project, and our clients got a ton of personal attention. That was our vision when we started out. We had thought we wanted to work like that forever.

It took a while for us to admit to ourselves that what we’d been doing up ‘til then wasn’t working anymore – and to admit that maybe it was time to embrace a new vision.

Second, I had to move out of my comfort zone – because this kind of perspective shift doesn’t happen without hard work. I was terrified of taking responsibility for someone else’s paycheque – and even more terrified of loosening my grip on my perfectionistic, control-freak tendencies and opening up to new ways of doing things.

Overcoming those fears, and learning how to stop letting them limit my vision, took a lot of work. And it was a huge step forward into living on purpose rather than just living by accident.

The third thing I had to do was make peace with being in a position of power. I had to learn how to be a good boss, cleanse myself of my bad-boss traumas, and get ready to be a real, honest-to-goodness boss.

This meant letting go of my desire to be everyone’s friend. It meant accepting that I would need to make tough calls about hiring and firing people. It meant learning how to instill values and vision into a team environment. It meant being lonely sometimes – because the tough calls fall to the boss.

Those 3 things – giving myself permission to change my mind; moving out of my comfort zone; and making peace with power – were things I had to fight for, and I’m constantly thankful for the lessons they taught me.

I don’t want to make it sound like the most important stuff is always hard. There is a beautiful ease that has woven itself through many aspects of my entrepreneurial journey, and I’m a firm believer that ease is a key metric of success – it’s just that it’s the nature of the easy stuff that we take it for granted, and it’s the nature of the tough parts that they stand out (and make a better story).

Looking back, I can see that I learned to code because I loved it; that I dropped out of grad school because I was just biding my time; that I fell in love with web design because it allowed me to connect world-changing people and organizations to their communities in meaningful ways; that I started my own company because I was born bossy and stayed that way; that I stopped coding not just because I couldn’t squeeze it into my schedule, but because I wanted to be involved in strategic decision-making on every project. And that I became a boss because I was ready to build something bigger, because it served my higher purpose of building a company that did better things than I could do with a smaller team, and because I loved going to work every day with the smartest, most wonderful people I knew.

It’s easier to see the meaning of things when we’re looking back on them. I now see love and purpose woven through every part of that story.

And I now look back on that time when I was fighting against the flow, using every ounce of my strength to cling to my old vision and avoid facing my fears, as a real coming-of-age moment.

Because I re-engineered my vision of success with purpose – dismantling the old, outdated dream that no longer served me, and designing a new one.

Because I faced my fears with purpose, working with mentors and coaches to chip away at them until I felt brave enough to move forward in a new direction.

And because I chose to become a boss with purpose – and only slightly by accident.

I wrote a short, and necessarily incomplete, piece for Quartz on Marissa Mayer’s statement that she’s not a feminist. You can find it here. I struggled to write it, because I knew I was leaving so much context out – and therefore leaving myself open to misinterpretation. So I am expanding on it here, to flesh out some of the things I couldn’t squeeze in.

This post is more personal than the Quartz piece; I hope it helps clarify my perspective.

We Have an Impact-Versus-Intent Problem.

I get why feminists feel betrayed when women they admire disavow feminism (especially when it’s done with a negative flourish that disses feminists, as Mayer did). It feels like a slap in the face to all of our hard work – hard work we are doing for the advancement of all women. So when one of us says, “I’m not part of your cause,” we can hear it as an unwillingness to acknowledge that the work is still underway, and that it’s important.

What bothers me, though, when I hear the chorus of outrage begin again, is that I remember, with painful clarity, a time in my young adulthood when I did not align myself with feminism – and when my feminist friends expressed their outrage and impatience with women like me, it made me feel small, excluded, and like I was not allowed to speak. I felt shamed for my ignorance and shamed for my difference. And I didn’t know how to talk about it without making it worse. So I stayed silent rather than risk deeper rifts.

I don’t believe that was their intent, but that was the impact it had on me.

They raged against ignorance, and I heard, “You’re ignorant.” They raged against misogyny, and I heard, “You hate yourself and other women.” Mostly, I felt their rage and felt afraid.

Multiple Feminisms

These days, I have a very different relationship with that outrage. Righteous anger can be a powerful tool, wielded responsibly and strategically. I have immense respect for intelligent expressions of outrage in the right context.

And I have tons of empathy for the fatigue that sets in when we see the bazillionth person today  fall back on tired stereotypes to diminish feminists. It’s effing hard to resist the urge to roll our eyes or fight back when we feel insulted.

But I really want us to resist the urge. Especially with women like Marissa Mayer, for whom I have great admiration. The last thing I want is for her to hear nothing but feminist outrage in response to her statement. What I want is for her to know there is room for her voice in feminism. That there’s room to be a newbie and ask clumsy questions while you’re figuring out where you fit. That there’s room to build your skills in acknowledging, analyzing, and working to disentangle one’s privilege from one’s accomplishments.

I also want her to know there’s room for thoughtful critique of feminism and feminists. That one need not label oneself a feminist in order to be a constructive voice in the movement for gender equality.

The labels don’t matter much to me, in the end. What matters to me is our willingness to listen, learn, and act with compassion.

A Story

A slight detour, to make a point: My father was a Protestant clergyman. For the first twenty-five years of my life, he led the weekly church services I attended. He is one of the most powerful, thoughtful preachers I’ve ever heard. And while he wrestled with the complexities and challenges of theology and scripture constantly, his faith had a strong core that carried him through many trials and tribulations. I always admired his commitment to God and wished I could feel the same connection he did to the divine. (I left the church in my mid-twenties, when I discerned that my commitment to music was stronger than my commitment to the faith – and I have not returned.)

Dad retired from ministry in the mid-1990s, and didn’t go to church much for quite a while, which I mostly put down to being picky about finding a preacher he enjoyed. (This is a common affliction amongst retired clergy.) And then one day in 2010, we were talking on the phone, and he asked me if I’d heard the news about novelist Anne Rice. No, I hadn’t. “She’s renounced Christianity,” my father told me, and then went on to say that he felt exactly the same way she did – that while he still felt a strong connection to Christ and to the Christian myth (he’s always called it “the Christian myth,” which I find rather inspired), he didn’t think he could stomach the idea of calling himself a Christian anymore, because the word has been corrupted by centuries of abuse and oppression.

I was stunned. The idea of my father – the minister! – not calling himself a Christian anymore was hard to make sense of. But what’s changed? Almost nothing. He still references scripture, and the great theologians, constantly. He still has the same spiritual beliefs. He still thinks deeply about the role of the church and its adherents in the world, and how Jesus’s gospel of social justice can teach us to be more equitable and compassionate.

But the word itself – Christian – is way too loaded for him.

And I get it, because hey, I grew up in a very secular community where every time someone new found out my family was Christian, I had to explain that we weren’t evangelical fundamentalists, we didn’t believe other people were going to hell, and we weren’t out to convert anyone.

And now I feel similarly about feminism. (Not that I think it’s been corrupted by centuries of oppression and abuse, obviously.) Not to the extent that I won’t call myself a feminist – I’m a proud, card-carrying feminist, thankyouverymuch – but I frequently ask myself, “Is it worth using the f-word here?” when I’m talking about gender.

Privilege and Multiplicity

Back to Marissa Mayer. Yes, she’s white, blonde, young, and conventionally beautiful. This gives her exceptional privilege – and it also makes her a target for hostility, backlash, dismissal, and more. (I ran a small business in my 20s, and let me tell you, you jump through a lot of hoops to get respect when you’re young and female in the business world.) She’s also a Stanford grad who was Google’s 20th employee (and their first female engineer). That gives her credentials and privilege, too – and it also makes her a rare breed who worked very hard to get where she is. And of course she has positional power, as the CEO of a Fortune 500 company, which again gives her privilege – and makes her a target for critique on the basis of  her class status, her capitalism, and her conventional definition of power.

My question is this: Does feminism not have room for her voice? I am strongly in favour of a pluralistic feminism that includes and celebrates the full range of women’s, men’s, and transgender persons’ experiences. I want to learn from everyone’s experiences of gender, race, class, ability, sexual orientation, ethnicity, colonialism, and other axes of identity. My life is richer when I make room for difference, with compassion and curiosity.

And I really, really want to learn from Marissa Mayer, who has lived an extraordinary life thus far and isn’t even halfway through her career yet.

The Invitation

The turning point in my relationship with feminism was when I was invited in with joy and love. When friends gave me books to read, and asked what I thought with genuine curiosity. When I saw women I could identify with – which for me meant smart, funny femmes with big smiles and ready laughs – talking about reconciling their love of high heels and makeup with their politics. When I discovered the world of intersectionality and couldn’t resist its intellectual depth and breadth. When my friend Liz held my hand through the purchase of my first set of cloth pads and compared notes with me as I unlearned years of shame and discomfort with my body.

These welcoming experiences laid the foundation for deeper, more complex interactions where my worldview was challenged in big ways. Trust must be built first, before we can have constructive conversations about privilege and power. We must let go of embarrassment, shame, and not-belonging before we can engage with courage and respect.

I fear that we have forgotten this fundamental truth of human relationship, in our quest to make ourselves heard. First, we must demonstrate that we can – and will – listen too.

I know there’s a diversity of perspectives on this, and I have great respect for the views I’ve seen expressed elsewhere, even while I disagree with some of them. As always, I welcome your comments.