Becoming a solopreneur? Why the way you work won’t work in your new venture

If you’ve struck out on your own or thinking about it, there’s a subtly that may deeply affect you. It’s called structure.

When I started out as a solepreneur nearly twenty years ago I was totally oblivious to it. Back then, in my enthusiasm to start my own firm, I didn’t give a second’s thought to how I worked, except this: I thought I’d have a LOT MORE TIME. I even went so far as to plan how I was going to spend that time on church ministry and other matters of interest.

It was a delusion. What I failed to recognize was that the work habits I had honed in one structure didn’t work so well in the other.

Becoming a solepreneur? Why the way you work won't work in your new venture


The corporate world provides tremendous benefits: A regular paycheck, known projects, the camaraderie of a team, a system of feedback and rewards, and (depending on the company) clarity of direction and priorities as assigned from leadership. My new venture had none of these.

Suddenly, on DAY 1 of my new job as a solopreneur, I was without a support system. If something were to get done, it would be me-alone. No admin to keep me on top of administrative minutia. No team to collaborate on ideas and projects. No one to offer encouragement and feedback. Just me.

So I did what seems instinctive when you’re alone. I looked around. And found others looking back.

One of the earliest things that those of us who venture out on our own discover is the amazing number of talented people who are doing likewise. A corporation’s talent structure is reflected in its org chart. Not so for the solepreneur. Instead, they instinctively pursue informal associations across industries and timezones the way schools of fish gather together to ward off predators. Both seek to project a bigger presence with the collective than they might as an individual. The collegiality of the collective encourages its members to stick together for survival and, in the case of soloprenuers, for the promise of future opportunities.

But the collective has a poor sense of direction. If you follow its lead you’ll sacrifice your own mission for mere opportunism. The needs of others can quickly end up on your list of to-do’s particularly if you’re trying to win acceptance. Even more so if you lack a healthy self-imposed structure.

Looking back on those days, I would been helped tremendously by giving attention to my own work structure. If I were to do it over again, I would have spent more time:

  • Clarifying my strategy and present objectives. In the corporate world, this is furnished by the firm’s vision and strategy. But asking, “What am I trying to accomplish?” is surprising too easy to neglect in your own venture. There’s two reasons for this. First, there’s the tyranny of the urgent (“I’ve got business to win!”); and second, there’s no one to challenge your thinking. When I first began my business, I raced ahead without giving much thought to the most important questions. My mindset was more opportunistic than strategic. I would have been better helped by taking some steps to stimulate my strategic thinking.
  • Establishing a routine. One of the advantages of being self-employeed is the flexibility of work. You can often work wherever and whenever you want; which may mean all the time. And that can spell trouble. Being always on, ever available, may make you a responsive hero to your clients, but it won’t take long before you lose a sense of direction. One of the most important disciplines to develop is the ability to think and act slowly. A structured work routine is critical for good strategic thought and it starts first thing in the morning.
  • Evaluating and celebrating my progress. The corporate world has very established feedback and celebration mechanisms. Performance reviews, salary raises, sabbaticals, and promotions encourage sustained performance. As a solepreneur, you have no such extrinsic motivators. Instead you must rely on your own accounting and creative rewards to remain inspired. That’s why clear goal setting is so important. You have no one but yourself to be accountable to. Sloppiness in this area is self-destructive. There were many days when I felt entirely uninspired and my work suffered for it. I even fired myself on several occasions. Clear goal setting followed by times of celebration can keep you off your own chopping block.

Creating a healthy work structure takes intentionality. It’s not usually the first thing you think about when becoming a soloprenuer. But these three simple principles, regularly repeated, can keep you as enthusiastic about your business as on the day you began it.

If you’re a solopreneur, or were at one time, what would you do over?

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