The Ever-Present Insecurity of Entrepreneurship

I readily admit it … I’ve been an entrepreneur full-time for 5+ years now, having enjoyed a measure of success I never dreamed of … and I still wrestle with insecurity on a regular basis.

It’s just part of the job. And those who overcompensate for it are typically the most arrogant ones that fall the hardest when things bottom out.

And I’m not talking about insecurity just in the low times when sales are trickling in or your new product isn’t taking off like you had hoped. That feels more like panic actually.

But especially in the high times, when things are just clicking. The engine is hitting on all cylinders. People are raving about you. And it seems like there is no stopping you.

This is when insecurity really creeps in for me.

I remember when we hit some significant milestones, like topping $1 million in gross revenue. I stopped for a second to realize the accomplishment (for me, it was a number on a piece of paper and a surreal milestone that enough people would exchange that much money for what we did in one year), and immediately began to think about the next day, the next month, the next year.

Could we keep the pace? Could we keep growing? Could we keep the momentum?

What products were in the works for release soon? What iterations and features were we already working on?

What were we doing to keep our customers happy for the next 365 days?

What is out there that could possibly blindside us now? What predator lurks in the shadows we haven’t seen yet?

(If you can’t tell by now, I’m a subscriber to the belief that pride comes before the fall.)

So even in the greatest of times, I tend to focus on the weaknesses and threats, more so than celebrating.

This year we logged five years of doing business. We now have over 24 people employed full-time. Some of them have kids and spouses supported solely by this business.

And even though we hit record milestones last year … and the trend seems to be going up for us … I still stay as low as I can to the ground … and preparing for the next obstacle or challenge.

In fact, humility and hunger are great productive byproducts of the never-ending insecurity of entrepreneurship.

I use them to keep pushing to be and do better, to keep our edge, to go farther and farther. To remind us that after every success, we’re not gloating and drooling after our own image in the mirror and thus taking our eyes off the real things that makes all of this happen (our customers).

Yes, you should celebrate. Yes, you should take time to rest and recharge.

You should do those things appropriately, reasonably and responsibly.

But there is a difference between climbing to the top of the mountain, savoring the moment and the journey for a time then moving on to the next challenge … and simply plunking down your gear and thinking you are finished forever because you’ve hit this peak so high that no one can touch you.

Success can make you lazy and lethargic. It can make you arrogant and boastful. It can make you blind and vulnerable.

But … success is fleeting. Nothing in business lasts forever.

There is always someone working diligently, often quietly in the background, to unseat you.

There is always another (better) option brewing in the works for your customers.

There is always another gig or company offering more [insert whatever benefit you can imagine] for your team’s best talent.

So … savor the moment when you get there. And remember the ups and downs of the last leg of the journey and what you can learn from them.

Then seek to stay low to the ground, while plotting your steps toward the next summit.

Because if you’re like me … that tinge of insecurity, like a creeping heartburn, whether it’s the small group of competitors behind you who are marching fast toward you, or the intoxicating illusion of success that leaves you vulnerable and weak, will remind you to keep pushing … onward and upward …

After all, if the journey is the real reward (and it is for me), then insecurity is simply your guide to keeping focused on the right path.

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6 thoughts on “The Ever-Present Insecurity of Entrepreneurship”

  1. Great post brother. Personally, I don’t believe you (nor founders in general) are alone. We live in our own worlds, worlds filled with the highs of brilliance, growth, etc and then the lows. Lows filled with self-doubt, insecurity, etc.

    Keep on, keeping on!

    • Sandip, thank you! As one of the most humble entrepreneurs I know, I take great pride in seeing your continued success and the burning fire in you to keep on the journey. It’s inspiring!

    • You bet man! The slumps comes … it’s tough in the early years (and even now) when things just are clicking or going as fast as you want.

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