The Pain of an Entrepreneur

An invitation to reinvent oneself, in humility.

Photo by Rahul Pandit from Pexels

Recently I had an honest conversation with a team of entrepreneurs. I recognised the pain they were voicing. And the odd thing was that I was surprised by my own recognition. Because, obviously, many of us who have been (and are) investing untold amounts of energy in their entrepreneurial project, have similar experiences. Only, we don’t talk about it.

I’m not alluding to the pain of failure in the market place, or rejection by potential clients or investors, which many experience as hardship. I’m talking about a sadly corrosive mix of aloneness, a feeling of not being understood and appreciated, and sheer exhaustion. They say it’s lonely at the top. It’s also lonely out front, at the entrepreneurial coalface.

Entrepreneurs tend to be ebullient. They seem to have boundless stores of energy. They believe in their project and do everything to make it succeed. They’re everywhere: deep in the operational stuff, the paperwork, the financial management, while non-stop networking, researching and strategising. And they genuinely want to please their clients, and be supportive and caring towards their co-workers and families. Believe me, all this frantic activity is shot through with genuine love and generosity. Entrepreneurs really don’t mind going the last mile.

But over time this starts to weigh. Obviously, the work goes on and on. And there is less and less satisfaction in it. Even the most exciting project or deal becomes a chore when it is smothered by the weight of a 12-hour daily grind.

But that’s not all. The entrepreneurs become progressively alienated, from themselves, and from their co-workers who are less deeply invested in their common project and, honestly, don’t really know what it takes to keep even a small organisation afloat (or so entrepreneurs think). Those who feel responsible for the whole continuously feel burdened by hard-to-manage complexity. “Bring it on!”, they tell themselves, resignedly. However, these founders don’t see their ruthless commitment reciprocated by their co-workers. Which leads them to take on even more. Someone has to do it, right? Meanwhile the members of the organisation feel increasingly oppressed and intimidated by their seemingly omnipotent, but merciless leaders. And hence less likely to step in and fill the gap, or put a hand on the shoulder of their tireless pacemakers. Barry Oshry identified this resentful dynamic as The Dance of Blind Reflex. This pattern is, however, neither personal nor specific to any given organisation. It is systemic. Taking it personal is equivalent to systems blindness. Which risks to fatally undermine the strength of organisational partnerships.

Financial motives may play into this. Co-workers look askance at the rewards that entrepreneurs assign to themselves. The latter, however, are keenly aware of a huge imbalance between, on one hand, financial return, and, on the other, hours invested and risk assumed. As careers progress, family commitments increase, and even the prospect of retirement starts to loom, this lopsidedness starts to grate. More fuel for the Dance of Blind Reflex!

But the biggest disappointment is still in store for the entrepreneur. This is the realisation that they genuinely are getting in the way of the continued success of their project. Their energy, ingenuity, patience and generosity are wearing thin. The magic of entrepreneurship has lost its spell. In the worst of cases, they have become a chagrined bore to themselves, to their families, co-workers, and clients. This realization is a moment of truth. Either they labour on, relying on sheer will power, or they accept the invitation to move on and reinvent themselves, in humility. It’s a painful affair either way. Clearly, only one side of the bifurcation carries a measure of redemption.

All this is human-all-too-human. And systemic. Often we are acting out parts in a play that seems to have been written by a mischievous hand. When we fail to recognise these patterns we are led to fuel our myths and prejudices about one another. Often, however, we can step out of this logic and choose to frame our dreams, relationships and circumstances in a way that reconnects us with our vitality. Entrepreneurship then turns into a joyful celebration of our shared humanity again.

Facilitator @ shiftN ⎹ Post-disciplinary researcher @ Newrope, ETH Zürich ⎹ How to create spaces were life is able to unfold, and is experienced as life?