What if you leave your job and can’t find another one?  What if you start your own business and get sick without health insurance?  What if your spouse gets tired of supporting your dream and leaves?

There will always be two choruses: those who think you’re crazy and those who advise “everything will be fine.”

Deep down, you want to listen to the voices of encouragement.  You want to give more room in your life to the positive instead of the negative.

But the negatives are pretty persuasive.

The truth is, neither group has any better idea what’s going to happen than you do.

They don’t know how committed you are or your level of grit.  They don’t know what skills you have, which you still need to develop, and how those compare to others in the field.  They don’t know your network or how much they love you.

Instead of asking whether bad things will happen if you make a change, ask how capable you are to deal with those events should they occur.

I recently wrote a post for Man vs Debt called How to Save Money Doing What You Love.  In the comments, one reader said

You’re right, I really shouldn’t use my finances as an excuse to stay in a soul-crushing career, but for now I have to put my head down so I can pay off some debt and accrue some extra savings before I take the leap. It’s hard not to be practical with a mortgage and a baby on the way.

He sounds a bit sheepish, at least to my ear, as if I was trying to convince him personally to leave his job and start his career anew tomorrow.  But in fact, he and I completely agree: practical is good.  Make a plan to pay off your debt … and do it.  Make a plan to sell or rent your house, or build up emergency savings, or provide stability for your spouse while they try something new.  Whatever your obstacle, make a plan to deal with it and do it.

But don’t mistake being practical for never changing.

Because there’s a hidden assumption here we have to address: no one can tell you everything is going to be okay even if you attempt to keep everything the same.

Several of my clients were unexpectedly laid off while going through my No Regrets Career Academy.  Career change went from feeling risky to essential.  They were glad they’d invested the time in developing a plan for change.

Being static is just as risky as changing.

So plan for the potential of an opportunity as much as you do its failure.

Where to begin?  What can you do now, today, to move closer to fulfillment without throwing away everything you’ve worked on so far?

Where do you turn for advice without jeopardizing your current job?

There are so many people talking about passion, strengths, north stars, parachutes–it’s enough to make your head spin.

While I deeply appreciate that you’ve invited me into your trusted circle, there’s value in having more than one perspective.

And today I’m going to help you cut through the noise.

I’m pleased to introduce you to five books I think every career changer should read.  Books that are well-written, bursting with actionable ideas, and even better, together have the ability to significantly up your game.

1. The Start-Up of You (Reid Hoffman, Ben Casnocha)

Have you ever read a book that made you feel like you were sitting in the front row of a Southern Baptist revival?  A book that so meshed with your ideas about a topic that you frequently found yourself shouting, “Amen!” and “Sing it!”

The Start-Up of You is that book for me.

It starts with a bold hypothesis: not only can everyone be an entrepreneur, they must.  Hoffman and Casnocha don’t mean that in a literal sense–not everyone will be happy running their own business.

What they are suggesting is that your career, especially today, is extremely fluid.  The guarantees that education and company loyalty used to provide are gone.  The only way to survive and thrive is to learn how to adapt and pivot.

And nothing teaches you those skills better than adopting the mindset of the entrepreneur and treating your career as if it were a start-up.

Some of the critical lessons in this book include:

• The art of pursuing your biggest dreams while reducing the risk of catastrophic failure (seriously counter-intuitive)
• Why 5- and 10-year career plans are a waste of time and you’re better off in “permanent beta”
• How to build strategic career alliances (Hoffman is, after all, the cofounder of LinkedIn)
• Why “keeping your options” open is career suicide

I could go on and on.  But the biggest reason I think every single career changer needs to read this book has to do with fear.

Talented, successful people come to me for help all the time.  It’s not that they can’t change, it’s that they’re deeply afraid.  This book will bust apart your outdated ideas on what’s risky and what’s not, and help you put together a career strategy you can live with.

2. Quitter (Jon Acuff)

I’ve long been an advocate for practical passion when it comes to designing a new career.  And nobody talks about this subject as convincingly as Jon Acuff in his book Quitter.

This isn’t a how-to book.  It doesn’t give you a step-by-step prescription for anything, not even quitting.  Because as he says in his book

Quitting a job doesn’t jump-start a dream because dreams take planning, purpose and progress to succeed.

This is practical passion at its best.  The book is insanely motivating, but not in a rah-rah, pep rally kind of way.  That kind of motivation may feel good in the short-term, but nothing will cause you to lose motivation and confidence as quickly as jumping into the deep end of the pool before you know how to swim.

As he says

Right now, the size of your dream probably outweighs your ability by at least tenfold.

Believe it or not, this is meant to be encouraging advice.  Because chances are, if you want to start over in a new career, you’re going to have to start at the bottom and work you’re way up.  And that’s a good thing.  Because when you’re back at the bottom, it’s okay to take risks and occasionally fail.  The stakes are lower, which makes for a better learning environment–exactly what the fresh career changer needs.

3. Never Eat Alone (Keith Ferrazzi)

Unlike the previous books which were published relatively recently, this came out in 2005.  As quickly as the world of online networking changes, you might think the advice here is obsolete.

I think exactly the opposite is true: the rise of online social networking makes Never Eat Alone more relevant, not less.

Social networking encourages us to focus on numbers rather than engagement.  It values broadcasting over conversation.  It lets us make friends that many of us never meet.

And that’s a shame.

I’m often asked for networking resources aimed at introverts.  While I suspect Ferrazzi himself is an extrovert, the strategies here are well suited to introverts because the fundamental currency advocated in this book is real human connection.  And that’s something that introverts not only value, but excel at creating.

4. Do More Great Work (Michael Bungay Stanier)

I’m a big proponent of test-driving your new dream career before you make the leap.  And chances are, you can do that without ever leaving your current job.

I already talked about how the book Do More Great Work helped me tame my to-do list and regain my sanity.  But this is so much more than a book on productivity.

At it’s heart, this is a book about finding your courage, a book that provides a series of exercises designed to make you comfortable with the uncomfortable.  It’s so easy to blame external demands on our failure to shine.  But the real enemy is fear mixed with a lack of clarity or prioritization.

One of many great concepts from the book is that “Great work is about doing what’s meaningful.  Great work isn’t about doing it well.”

At first you wrinkle our brow in confusion.  Great work is poorly executed?

No, but it’s a reminder that great work is often at the edge of our competence, and sometimes the impact of our work is less in the delivery than in the heart that sparked it.

5. Status Anxiety (Alain de Botton)

If you enjoy reading The New Yorker, you’ll surely enjoy Status Anxiety, an intelligent and historical perspective on our growing obsession with other people’s opinion of our work.  de Botton speaks to the over-achievers, many of whom find their self-image can be likened to

[..] a leaking balloon, forever requiring the helium of external love to remain inflated, and ever vulnerable to the smallest pinpricks of neglect.

If you have ever struggled with your innate desire to achieve traditional success, while simultaneously engaging in self-flagalation for doing so, then this book is a must read.

Fantastic five book give-away

In the interest of transparency, I note that Random House sent me a free copy of The Start-Up of You in the hopes I would review it.  You should know I receive many books, from publishers and authors alike, but review very few of them.  This book not only makes the cut, but is one of my new favorites.

The links to all the books above are Amazon affiliate links, which means for every book purchased, I earn a small commission.

It also provides a mechanism for me to share the wealth.  That’s why I’ve decided to do a fantastic five book give-away.

Everyone comes to career change with their own issues.  Some of you may still be on the fence, wondering if you can really pull off a Clark Kent to Superman transformation with your career.  You should read Quitter.

Others may be struggling to test-drive their newly formed career plans.  You should read Do More Great Work.

Given this diversity of interest, I thought it might be fun to give-away one copy of each of the five books above to those who need it.  I’ll send the book absolutely free of charge anywhere in the world.

To enter the book give-away:

Leave a comment below stating which book you’d like to win and how it would help you.  You may post anonymously, just make sure to use your real email address so I can contact you if you win.  Your comment should be for ONE book only, but you can leave as many comments as you like (i.e. you can enter the contest for all five books, but that will require five separate comments).

Winners will be selected and contacted via email on May 10 at 7 AM EDT.

That means you have roughly 48 hours to enter.  Don’t put this off–just write what comes from your heart.  How might one of these books help you get where you need to go?

I don’t normally make this plea, but please share this post on Twitter, Facebook, or even email.

So many people feel trapped in careers and wonder how they can get more from life.  In this day of information overload, one of the nicest things you can do for people is to share with them material that makes a difference and is actually worth reading!

Know of a book I should have included?  Let me know in the comments.

But the day I started my business?  Now that was scary!

In retrospect, that level of fear is laughable.

But I remember feeling so completely overwhelmed by the idea of trying to make money by myself.

How do I start?  What if no one wants to work with me?  Am I in danger of creating a money pit that loses far more than it gains?

What if I’m just not cut out for this entrepreneurship thing?

On and on the questions went in my head.  So I proceeded the way any nerd would: I enrolled in courses, bought books, and signed up for masterminds.  My quest for knowledge was, let’s say, thorough.

Over the course of 18 months, I spent nearly $30K learning how to start and sustain a business.

Wow, now that was dumb!

In my defense, I had no idea which courses and teachers were worth the investment and which weren’t.  When you have no idea where you’re going, it’s easy to just follow the crowd of self-improvement junkies who plan to take one more course before launching.

The only thing that saved me from that ball and chain of expenses was that I actually implemented what I was learning and in turn, fell in love with running my own business.

Today I’m going to give you the benefit of some of my experience.  I’ll introduce you to three inexpensive alternatives to learning the ropes that will quiet the questions in your mind and finally get your business off the ground.

1. Find a bargain

Once or twice a year, the Only72 team brings together a bundle of courses and books for 1/10th their original cost.  The themes vary, but this time they’re celebrating the launch of Chris Guilllebeau’s book The $100 Start-up with a new entrepreneur package.

For just $100, you not only get a physical copy of Chris’ book (shipped free anywhere in the world), but you also get access to courses that teach you:

• How to build a blog community that wants to buy from you
• How to balance your business with the needs of your personal life
• How to sell your products and services without feeling like a slime ball
• How to turn your passions and hobbies into viable businesses

And much, much more! (I know that sounds cheesy, but seriously, go check it out and see for yourself. And yes, that’s an affiliate link.)

Of course, you don’t just buy this package because you want some good business tips.

The hidden value is the opportunity to find a successful model you can mimic.

Many are interested in the business of selling information products.  If that’s you, it’s absolutely critical you understand what a successful product looks like and delivers.  While these products may not be your direct competitors, they’re excellent examples to dissect and learn from.

This package gives you a chance to check out 18 different products for just $100–invaluable information to see the variety of approaches you can use to package your expertise.  Just remember, the sale only lasts for 72 hours and counting!

2. Find an internship

This is a fantastic (and free) way to learn the ropes of running a successful business.

The basic idea is this: find someone you’d love to learn from and ask to intern for them.  You probably don’t want to pick someone who will become a direct competitor, but someone working in the same space is a good idea.  So say you want to open a cafe, then you might intern for an in-demand caterer.  If you want to become a professional finance blogger, you might intern for a professional blogger writes about healthy living.  You get the idea.

These kinds of gigs are rarely advertised, mainly because most budding entrepreneurs are too busy and scared to expand their business.  But you shouldn’t let that stop you.  Think about the services you can offer and pitch the person you want to work for.  If you’re having a hard time figuring out your value, find other interns doing that kind of work and ask what they do.

But here’s the important thing: don’t do the work for nothing.  An internship isn’t a gift.  Ask to be mentored or advised in exchange for your services.  Ask for testimonials and referrals.

How well does it work?

I put out a call for interns last year and got a dozen applications from amazing people I couldn’t have otherwise afforded at that stage of my business.  In exchange, I provided private mentoring to each and gave them a inside look at how I run my business.  I not only showed them what I do, but why I do it that way and how I make my decisions–information they can directly apply to their own work.

The results were beyond what any of us were perhaps expecting.  One was able to quit her job within a month of the internship and by the end of it, was already earning more than her previous full-time job.  The other started a business as a side-gig (we also navigated a promotion for her full-time job) and just signed her first major client: me.

And while I’d love to tell you that the special sauce was that one-on-one mentoring, I think the real magic was seeing that running a business was much easier than either imagined.

They just needed a model to fiddle with and make their own. The genius was all theirs.  I just helped them channel it.  With the right mentor, you can do the same.

(As an aside, I’m going to be sending out a call for new interns next week to my email subscribers only.  If you’re not on my list and you’re interested in interning with me, make sure you sign up here.)

3. Find a sounding board

One of my biggest advantages when I got started was having a couple of trusted advisors who I could quickly bounce ideas off from time to time.

Because sometimes, what we really want is just someone who knows what they’re talking about to say, “You’re not crazy.  Try it.”

Obviously, if you take advantage of the internship, you’ll have that.  But interning isn’t in the cards for everyone.  Maybe you’ve been laid off and you need to start making money now.  Or maybe your full time job only leaves a handful of hours a week for something on the side, and you want to spend it building your business, not someone else’s.

Despite getting many requests teach new entrepreneurs, I’ve been reluctant.  After all, there are already so many books and courses on the subject.  Was I certain I could add something new and of value?

That’s when I realized what was missing was that sounding board: an inexpensive way to get experienced advice on your business ideas.  So I decided to open the Bright Entrepreneur’s Club.

I’ll be talking more about the Bright Entrepreneur’s Club in the coming months, but if you’re interested in getting free insights from me and interviews with successful entrepreneurs, as well as exclusive offers to participate in my “sounding board sessions,” you can sign up here.

Just do it

Starting a business is scary.   When I sent out my first email looking for clients for my career course, I thought my heart was going to chisel its way right out of my chest.

If you wait until you know everything you need to know, you’ll never get started.  But if you jump right in without any background, well, your ventures are much more likely to fail.

Not that I think that business failure is necessarily a bad thing.   Few experiences are as instructive.

And you should never lose sight of the fact that there’s a huge difference between a failed venture and a failure as an entrepreneur.

Between you and me, though, failure just isn’t my favorite learning tool right out of the gate.

Let me get a few successes under my belt.  Let me build some confidence before I get knocked down.  Then give me a community who will offer their hand and pull me back on my feet.

That doesn’t mean it will be easy.  But starting a business doesn’t have to be the expensive, solitary experience many of us imagine.

So what are you waiting for?

You can do it.

By and large, he was happy.  But then he turned serious and asked me, “Can you handle some honest feedback?”

I took a deep breath.

He’d noticed that I had the habit of panicking when I felt I had too much work on my plate, and then rashly canceled on my commitments.

I didn’t necessarily disagree.  I knew I had the habit of signing up for too many activities and projects, mainly because I’m easily excited by opportunities to problem solve.  When my to-do list got to be more than I could handle, I re-prioritized and either wrapped up or backed out of the work that no longer suited me.

What was wrong with that?

He pointed out that not only was I clearly suffering emotionally when I felt overwhelmed, but I was hurting my professional credibility as well.

He told me I had a time management problem.  I argued I had an over-commitment problem.

Over time, I realized he was right.  And the problem was far worse than I realized.

Fortunately, I discovered a process that, with just one day of concentrated effort, allowed me to take control of my calendar, break my enthusiastic tendencies to over-commit, and finally (finally!) let me feel in control.

Today I’ll show you step-by-step how I did it.

Do more great work … up to a point

In his book Do More Great Work: Stop the Busywork. Start the Work That Matters., Michael Bungay Stanier highlights why we need to be conscious about managing our time between bad, good, and great work.

When I worked in the corporate world, most of my work fell into the categories of bad and good work. Bad work is the pointless, meaningless work that wastes your time but someone inexplicably keeps asking you to do it.  Good work is the vital, useful, and profitable stuff that keeps organizations running.

But it’s the great work most of us are interested in.  For organizations, it’s the stuff that drives strategic difference and innovation.  At the individual level, great work inspires and engages.  It is deeply meaningful work that connects to your aspirations.  But Stanier also provides a warning

Great Work is also a place of uncertainty and discomfort. The discomfort arises because the work is often new and challenging, and so there’s an element of risk and possible failure. Because this is work that matters, work that you care about, you don’t want it to fail. But because it’s new and challenging, there’s a chance that it might.

This is an issue no one talks about as you consider making the transition from a decent career to one you love.

You will be tempted, particularly the over-achievers among my readers, to take on more great work than you can handle.  For the first time in your life, you might see your full potential reflected in every project you consider, every collaboration.

Those of us who already have a tendency to over-commit can very nearly drown when surrounded by opportunities to pursue great work.

As Stanier brilliantly puts it

What are you saying yes to? And by saying yes to this, what are you saying no to?

In many cases, we’re saying no to sanity, to sleep, and to professionalism.  And the worst part is, we largely don’t even realize we’re doing it.

The step-by-step plan to sanity and fulfillment

While it’s not really necessary to show you the actual projects and decisions I wrestled with, I want to walk you through my thought process.  It all started with making three very important lists.

Step 1: Capture how you spend (and want to spend) your time

So let’s start by focusing on the positive.  What are the things I definitely know I want to do (in no particular order)?

1. Give a TED talk
2. Continue some sort of offering for the No Regrets Career Academy
3. Write books
4. Creative marketing (e.g. make “viral” videos)
5. Interview series
6. Continuing my education (books/seminars/masterminds)
7. Grow my blog
8. Spend quality time with my family

Now what are the things I think I’d like to do?

1. Seminars & workshops for corporate settings
2. Client mastermind program
3. Find sponsors for my work
4. Put on my own live event
5. Regularly scheduled coaching calls
6. Travel

Finally, I annotated other activities that take up my time.  This will include things like sleeping, eating, and chores.  But it also includes good work, stuff like answering blog comments and (ahem) my Reserve work.

Step 2: Analyze for “critical mass”

The first thing that struck me just looking at these two lists is: no wonder I often feel inadequate!

Nearly every activity on the two lists above is a big project requiring focused effort, a lot of learning, and connecting with the right people who can help me move it forward.

For example, I’ve been frustrated that my number of blog subscribers has been stagnant for several months now. I fooled myself into thinking I’d reached the point where I could just write a great post every week and the numbers would magically rise on their own.

Growing my blog requires an investment, one I couldn’t provide because I was too busy working on other activities on my dream list.

In fact, my lack of focus actually meant in some cases, I was losing ground.  There’s the concept of critical mass, and in most cases, I was spread too thin to reach it.

For each of the tasks on my list, I made a guess as to how many hours a week I thought I needed to reach critical mass.  These are estimates for now, and in all likelihood are probably still too optimistic, but it’s a place to start.

Step 3: Put some ideas in the “ice box”

We all know there’s only 24 hours in a day, but many of us conveniently ignore that fact when deciding how to spend our time.

I’m not suggesting you give up on your dreams.  Quite to the contrary.

I’m suggesting each needs its own space to breathe and grow.

I can see myself up on that TED stage.  I really want to make that happen.  But I also know that will probably be a much easier task once I’ve accomplished some of my other great work ideas.  I can save it for later.

I also realized that given all the big items on my “definitely want to do” list, nearly everything on my second list of “would like to do” would likewise have to wait.

Lastly, I took a number of items off my “stuff that takes my time” list by outsourcing them.  I hired a housekeeper.  I hired a travel agent.  Does it cost more to do that?  Absolutely.

But this exercise helped me see the invisible cost I was paying by not getting help: I was constantly stressed out and unable to focus on what mattered most.

Step 4: Set your core work hours

To further simplify the process, I created core work hours.  The concept is a little like skimming money off the top of your take-home pay and putting it into savings.

Basically, you set aside time for the things of greatest consequence.  Your core hours are the hours that remain.  And that is what forces you to get serious about prioritization.

I came to my core hours by setting some fixed parameters:

• The time from when my daughter gets out of school at 3 PM to when she goes to bed at 8 PM is set aside as family time.  This obviously includes dinner, but might also include chores that can be done together, such as grocery shopping.
• I stop working at 10 PM every evening.  This ensures I have time to let my mind wind down and get at least 8 hours of sleep, since normal wake-up time in our house is 7 AM.
• My weekends should largely be reserved for more family time, socializing with friends, travel, chores, or just plain ole down time.  My only exception is from 8 to 10 PM on Saturday and Sunday.

This gave me 44 hours of core working hours.

Step 5: Build your ideal week

You’ll remember in Step 2 we set aside the hours we thought we needed to reach critical mass. Now the trick is to fit these on the calendar within the core work hours you’ve designated.  I found the best way to do this is to just draw it out.

A few tips to keep in mind:

• Some activities, like continuing education (shown here as CE), can easily be broken into small chunks.  But many activities benefit from concentrated focus.  Be honest about these, and if you can’t give an activity the critical mass and focus it needs, maybe it needs to go in the ice box.
• An ideal (and free) tool for managing the number of tasks you’re working on at any one time is Kanbanery.  You can set lists for to-do, doing, and done.  Best of all, you can limit the number of tasks in your “doing” list.  I love it!
• Create time for the unexpected, infrequent, and less than ideal.  Things like doctor’s appointments, travel, visiting relatives, etc.  Your schedule has to have some slop or you’ll drive yourself insane.
• You have the ability to break your own rules.  Finishing up a big project and want to work all weekend?  You can!  The ideal week schedule allows you to make conscious decisions about how you want to spend your time.
• You can move things around as needed.  For example, this schedule provides 8 hours for coaching a month.  I can do that in 2 hour chunks each week, or I can take 2 days each month at 4 hours each.

Step 6: Where’s Waldo?

Believe it or not, you can go through all these steps and still realize you forgot something important.

For me, as I looked at my ideal week, a light bulb went off when I realized there was no time for going to the gym.  My life (and fitness levels) up until now started to make a lot more sense.

I had several choices:

• I could remove some core work hours
• I could adjust my parameters (for example, one day a week I might get less sleep)
• I could outsource some of my regular work, like getting my daughter ready for school, to my husband one day a week, then use the other two options for the rest of the time.

The point is, the choice was mine, and for the first time, I could accurately weigh the consequences of whatever I decided.

Is this a fantasy?

In the past, I told myself I just had too much to do.

As Alice Walker says

The most common way people give up their power is by thinking they don’t have any.

You decide how you want to spend your time.

Not everyone wants to hear that message.  For the longest time, I know I didn’t.  Being busy, overwhelmed, and in-demand seemed like the hallmarks of success to me.  That didn’t change when I left the corporate world and decided to work for myself.

I acted as if a burden was being thrust upon me, instead of acknowledging it was one I was choosing to carry.

That doesn’t mean that lots of people won’t rush in to tell you what they think you should be doing with your time.

Your boss, your spouse, your friends, your co-workers … they all have demands.  Some of the demands and distractions will even reside in your own head.

All I’m saying is: it’s your choice to listen.

The fact that my most successful blog post was written over a year ago.

I used to think jealousy was one of the worst emotions you could experience.  I hated myself for wasting time analyzing other’s news clippings or subscriber numbers.  It flew in the face of my own teachings about defining success for yourself.

Then I realized one emotion was worse: inadequacy.

Inadequacy is ruthless about detail.  It notices how no one talks to you at the PTA meeting or how irritable you’re being with the family you love after a bad night’s sleep.  It makes fun of your clumsy bump over the curb (again) while driving in a foreign country.  If you’re blogger, Google Analytics becomes the yardstick of your self-esteem.

On the other hand, inadequacy is blind to your wins, big or small.  It discounts, minimizes, and forgets.

You can remember saying to yourself, “If only I could…” and then when you did, it was overshadowed by what you didn’t.

Only a couple of years ago, I fantasized about reaching 1000 subscribers and building a business that brought home an extra $2000 a month for our family. That seemed wildly successful to me at the time.

Now that I have thousands of subscribers and my business cleared nearly $7000 last month (an unusual month and certainly not average, but still), you’d think I’d be euphoric and celebrating non-stop.  Nope.

I’ve struggled to shake the feeling I’m somehow falling behind.  It’s not that I don’t recognize that I’ve had some successes.  It’s that it often doesn’t feel like enough.

I’m not courted by media as a career expert or connecting with the all the big influentials.  I despair I’ll never reach 10,000 subscribers (an order of magnitude above my initial goal).

How in world can I hope to realize my dream of being a writer, the voice in my head whines, if I can’t even compete in the world of blogging?

Maybe it’s just me, but I’m pretty sure successful, “inspirational” bloggers aren’t supposed to admit they feel inadequate … ever.  For someone who claims to be “an optimist at heart,” this only doubles my feeling of failure.

Believe me when I say this admission is highly uncomfortable.

But it’s also real.

And after wallowing in some self-pity for a while, I learned that feeling inadequate isn’t nearly as bad as I thought it was.  Here’s how to get perspective on the problem and channel the emotion for good.

Two big reasons we feel inadequate

The tyranny of should

Penelope Trunk says “Should is the American way of putting ourselves down in the name of the need to impress other people.”

This is the first source of inadequacy, when we think we should have something we don’t, often (though not only) because we want respect and admiration from others.

I feel like journalists should be coming to me for interviews.  I think conference organizers should be inviting me to give talks.  I think I should have more comments on my blog posts.

But how important is any of this?  Was it actually worth feeling bad over?

I realized most of my should’s weren’t needs, but wants and desires in disguise.  They weren’t essential to my personal definition of success.

That doesn’t mean I shouldn’t want or have those things. But to get them, I’m going to have to do something more or differently than I am today.  No one owes me anything.

In this way, should becomes the whip that over-achievers use to work harder and drive ever better performance.  The truth is that the tactic largely works, but when overdone, it’s a recipe for disappointment.  On the other hand, it gives me a list of really concrete things I can start doing to feel better and move me forward on my goals.

It’s important to remember that just because you come up with your own definition of success doesn’t mean you won’t be lured by society’s siren song from time to time.  It’s why I recommend printing it out and putting it somewhere prominent, so you can remind yourself what you’re really working towards.

Big goals, big emotional roller-coaster

In a webinar for my No Regrets Career Academy clients last night, Jonathan Fields talked about fear and failure.  He reminded us that if we’re not failing at least some of the time, we’re not likely to ever achieve those big goals we dream about.  The other side of risk, he said, is opportunity.  You can’t have one without the other.

Big goals mean you’re going to have to learn new things and take on tasks you’re not very good at yet.  If you’ve been playing it safe and riding the coattails of your talent all your life, this is going to make you feel pretty lousy.

This means feeling inadequate can actually be a sign that you’re on the right track.

Believe it or not, you can take pride in your feelings of inadequacy if they stem from doing what’s hard.  I value learning and challenge, even if the process isn’t always pleasant in the short-term.

Plus, you’ll find you’re in really good company.

How Zach Braff and two ants helped me ditch the self-pity

If you’ve ever watched the TV show Scrubs, you’ll know Zach Braff is famous for his comic and deeply honest insights on life.  So perhaps it’s no surprise that his play, All New People, provided the release I needed from inadequacy.

His character, who is going through a rough time after a break-up, watches two ants fight over a crumb of Poptart.  From his perspective, he realizes the struggle is largely meaningless.  There are other crumbs.  Regardless of who wins the prize, both ants will eventually die and be replaced by other ants.

The message isn’t that life is pointless.

It’s that fighting yourself is pointless.

And that’s what self-pity is: a big punch in the face by your own hand.

You need a fight?  Fight the system.  Fight injustice.  Fight for your ideas.

And know that if you’re doing it right, sometimes you’re going to feel completely and utterly inadequate.

Maybe that’s what inspiration is all about.