You Might Be Completely Wrong About Your Shortcomings

For most of my adult life, I was the very last person I thought would be cut out for entrepreneurship. The VERY last. I don’t have what it takes, I told myself, over and over again. For years.

In my early 20s I came to the following conclusions about myself:

  • I am a planner, I am not designed to handle uncertainty well.
  • I am very attached to financial security and to responsible spending and saving; it doesn’t make sense for me to walk away from steady income.
  • Other people have the big, creative, innovative ideas, not me. I’m a great implementer.
  • I am not a minimalist and I don’t want to live out of a suitcase — if being an entrepreneur means eliminating all my creature comforts, I’m not cut out for it.
  • I will sink without the structure or interaction of going in to work every day.

And why wouldn’t I believe these things about myself?

I am a GREAT rule-follower . . . maybe even one of the best. If I’m on time, I’m late. If I accidentally drop even the tiniest piece of trash, I pick it up. Karma! Half the time when I’m walking down the street if I see a piece of trash in my path, I pick that up too.

I have always been a straight-A student (and admittedly, a teachers pet). I played Varsity softball for four years and got the Coaches Award every year. Not MVP, for actual skill, but Coaches Award — the one for following the rules, showing up, work ethic, leadership and being a great team-player.

I moved quickly up the ladder at Google because I was outstanding at playing by the explicit and implicit company rules. And hey — I liked it!! I thrive on positive reinforcement, structure, and feedback.

So, as my book and blog “side hustle” started to grow and I started to get overwhelmed, I was almost forced to think about the possibility of leaving. But every time I thought about quitting, I told myself that would be stupid. I’m not one of the “entrepreneurial types.” I’m a rule-follower, and that’s just my lot in working life.

But when I thought about where this work ladder was taking me — up to middle-management and maybe even a big-shot director or CEO someday — I realized I wanted no part in it. The stress, the intensity, the responsibility.


How To Reconcile This?

I had to start to ALLOW for the remote possibility that maybe, just maybe, I was wrong about myself.

Maybe I was smart enough to figure out how to create my own structure, my own rules. Maybe not, of course. But there reached a point at which I was no longer willing to keep locking the little bird cage I had created for myself.

Shifting my perspective opened the latch. For a few months I stared at the open door. Should I fly out? At this point, I was the only one keeping myself locked inside.

What finally gave me the courage to take the leap into self-employment was NOT a belief that I was born to be an entrepreneur. It was the willingness to admit that “I don’t really know what I’m cut out for, and I won’t know until I try.”

Time To Fly.

So I quit, and now it’s been a few years. And several of my biggest fears have come true!

I worried about being uncertain about what I wanted to do long-term. I worried about dips in finances, I worried about how I would transition after Life After College.

But you know what? Those are what keep this crazy adventure interesting! They are not nearly as debilitating as I imagined them to be (only sometimes ;)).

Here’s a really interesting physical manifestation of all this: my weight used to yo-yo up and down a 20-pound spectrum of lean-mean workout maniac to bloated stress case. I could never quite seem to keep it steady, and it was always SUCH. HARD. WORK.

I lost 20 pounds pretty quickly after I quit, and it has stayed off for two years with relative ease. Not by being a couch potato, but because I’m able to prioritize my health and happiness, every day. I love movement. Given the ability to set my own schedule, it’s a joy to include a walk, yoga, and/or pilates on every day that I possibly can. I haven’t had alcohol since New Years because I finally admitted it doesn’t serve my health, my mood or my creativity.

Quick aside: I no longer have a watercooler, printer, lunch spot, or co-workers’ desks to walk back-and-forth to all day — just my desk (from the bed), the refrigerator (boredom and procrastination danger zone) and the bathroom. In a small NYC apartment. If I didn’t schedule my day around fitness and movement, I’d be in trouble!

Financially, I have cut back my spending (and saving, but I plan to change that), but I’m okay with it for right now. This is a building phase, and although I do worry at times about where the next income will come from, it’s not nearly as bad as I thought. I kind of enjoy the detachment from STUFF. Even as a routine-lover, I much prefer travel when given the choice of where to spend my money and my time.

On the whole, I am the most content with my career than I’ve ever been, even in such a big transition year where I’m still figuring a lot out. I happen to love the life of entrepreneurship. The total freedom to fly from the seat of my (yoga) pants.

There has not been one moment since quitting that I wished I was back in an office, and I won’t go back if I can help it. Absolutely no judgment or offense to those who do thrive in the big team environment, but I shocked myself to realize that I’m actually not one of them. Who knew?!

You Don’t Know What You’re Cut Out For Until You Try

Whatever big leap you are staring down, consider ditching the question, “Am I cut out for this?” Try the following instead:

Do I fundamentally believe that I am creative and resourceful, and can figure things out as I go along? Am I at least willing to TRY?

As a wise man often reminded me: never try, never know.

Is there someone in your life who is doubting themselves right now? Consider sharing this post with them . . . not as another wild n’ crazy “I quit and life is glorious island-hopping perfection!” story, but as a little wake-up call that they might be completely wrong about their own shortcomings. It might just be time for them to open their own cage door.

And hey — these big leaps are epic personal growth journeys no matter what. Surely the new litany of actual shortcomings will rear their inevitable little heads in no time. :)

I’d love to hear from you in the comments:

When have you surprised yourself with what you are capable of? In what ways were your fears completely wrong or misdirected?