When to leave your company

You speak to advisors. You wrestle inside yourself between competing stories, one in which you ought to acknowledge it’s time to move on and tackle the next mountain, and another in which your path echoes those of heroic entrepreneurs who nearly hit bottom, and then rose to orbit. Either story has more appeal depending on the day. Your internal compass, your instinct, is useless here so you turn to decision matrices and to the writings of others who will tell you definitively one thing or another. And yet, the coin in your own mind turns up neither heads nor tails. So you begin to make halfway compromises: “maybe I’ll just focus on my passion and have someone else do the admin stuff”. You don’t know which path to attach to, and the whole process generates heartaches and headaches.

All the while, this happens in stealth. Most times, you can’t divulge your internal mess to your team, partners or investors. And most times, when someone asks you how your company’s doing, you still spit out the same script — “great, we just did X, which I’m really excited about”- to project momentum.

Every entrepreneur has, is, or will go through this turbulence. So where do you go from here?

The Twisted Psychology of Entrepreneurship

At the heart of this is a tension between two virtues we’re told make us great entrepreneurs: irrational commitment, and irrational willingness to let go.

Irrational commitment is the protagonist in every entrepreneurial hero story. When nobody believed you could build a company, you shrugged off naysayers and did it anyway. When faced by impossible odds, traversing a terrain of Murphy’s Law, you doubled down and pushed through. It is common expectation that you sacrifice your time, money and sanity to building this thing up-hill. No surprise then that entrepreneurs call their companies their ‘babies’, and treat them like helicoptering parents.

Irrational willingness to let go is the emotional detachment shrewd poker players portray when cutting their losses or saying no to a tempting bet. It’s you being willing to ‘kill your baby’, or leave it to someone else because some fundamental aspect isn’t working, and you can reinvest your energies in something else. It’s a story seasoned entrepreneurs have, but is told less frequently.

These two concepts are incompatible in the same instant. To be coldly willing to let go feels like alienation from your past love affair not just with the company, but to the meaning it had for you, to the glory or interesting narrative it bestowed on you. It can feel like acknowledging the failure so many expected of you. And to be irrationally committed can feel like self-delusion, ignoring the wise advice of people who can see your forest for its trees.

Every time something goes wrong or the company underperforms, these two collide in your gut. So if you can’t trust your instinct, or the advice of others, what can you do?

Remember, Life Is Impermanence

Things that appear like solid pillars of our reality are not. Rather, it’s better to think of them as “prominent now”.

Oxford University traces its known origins to 1096, which is a useful milestone for the start of the modern era of universities. That’s only 10–15 full lifetimes ago. The Magna Carta was 9–11 lifetimes ago. American sovereignty, 3–5 lifetimes ago.

Of the original 12 Dow Jones Industrial companies from 1896, only one is still around (GE). The whales by which we measure the American economy, all of them experienced an arc from ascent to descent. None was so solid as to be impervious to time and circumstance.

And that’s true of all companies, even the ‘successful’ ones. Each travels along an arc with a specific time horizon. Yours will too, no matter how it performs.

The thinking then moves from absolute commitment, to “which part of the life cycle am I participating in?”, which is a more actionable question.

The Right Question To Ask Yourself

The reality is that the question of staying or going is not a question about the company, or the market, or the right partners, or any other external proxies for your internal reflection. It is a question of what story about yourself you are operating on.

How does staying serve the story you are telling yourself about your life? How does leaving do the same? Do they deflate and challenge what you think about yourself or do they reinforce and fulfill it?

And why is this the story about yourself you’ve bought into? What other stories are possible?

If staying staves off the ridicule or disappointment by loved ones, that’s what you’ve got to work on. If leaving allows you to avoid dealing with responsibilities or partners you know you probably should deal with, or to ditch the messy reality of a project half-done for a shiny blank canvas, that’s what you’ve got to work on.

All the rest — market analysis, performance forecasting, assessing other opportunities, stewing over personal conflicts — typically happens in service of either changing or strengthening what you want to believe.

In other words, the question of staying or going is only there as a result of your mental/emotional model. It is a red herring for what actually matters, because the stories you tell yourself about yourself will follow you to every endeavour you take on, every relationship you jump into, every opportunity you consider, every hardship you endure. Once, and only after, you inspect that, the question of staying or going will answer itself.

There is no other magical maxim, no Paul Graham truism, no universal litmus test that will instruct you well. It’s all noise that distracts from the signal you’ve got to find; the one nested inside how you think about yourself.

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