Lean In – To Your Own Business

Homework with a laptop

So, if I’m getting the national zeitgeist right, it’s time to “lean in” and pursue opportunities that will take me to the top – the “top” being defined as a commanding leadership spot at the head of a Fortune 10 company, and at least one seat on a corporate board. This, so I’m being told, is the ultimate definition of success.

And, yet, this narrow definition of “making it” seems a little confining to me. Especially when I read Intuit’s 2020 Report, which projects that 40% of the US workforce will be doing freelance, micro-business or contingent work within the next ten years. Forty percent.

Makes the terms for defining one’s success a little different, doesn’t it?

If you control your own schedule, is that success?

If you continue to learn and grow and make a difference in the world, is that success?

If you meet all of your financial benchmarks, is that success?

If you have no boss, like a CEO does, but have clients, like a CEO has a Board of Directors, is that success?

I say yes. Yes, that’s exactly what success looks like.

In a lot of ways, it’s never been easier to start a business. Technology is easy, and relatively cheap, and organizations are hiring freelancers.

But it’s rather scary to take the leap.

So, what’s holding most people back?

First, it’s the outdated idea that the ultimate expression of success is derived from a big leadership role within a large organization. We know this is not the only measure of success, don’t we? But, boy, is it hard to let go of the way our parents and their parents and our peers and their peers have experienced work and defined success in the past.

Second, it’s the narrow thought that the only work day that matters is 8am to 8pm – you know, the typical ambitious, over-achiever, “I’m so busy!” mindset. We know it’s more about quality than quantity, but the old “hours put in on the job equals effectiveness” is pretty hard to shake.

Third, and I see this quite a bit in my coaching work, it’s the feeling that we’re all supposed to have a boss who tells us what to do. Who are we if we are independent, and self-directing, and self-starting? Who do we have to blame if it’s all on us?

From my own experience, all I can say is this: I haven’t had an office job since 1996. In 17 years, I’ve only reported to an office outside my home to work with clients at their request. Most of my work has been delivered remotely by conference call, video call, or other technological means. I haven’t messed with commutes, I don’t have anyone to approve my vacation time or question me about sick leave, and there have been mercifully few instances of nasty office politics (those clients I fired as quickly as I could, believe me).

Over all those years, I’ve built a right-sized business for myself which has allowed me to serve my clients, meet my financial needs,  and honor my key priority – which is being a good-enough parent to my kids.

And maybe I’m just an early adopter. And maybe in the next ten years many more of you are going to join me in this rewarding, free-form work of our own design.

My advice? Go into it willingly, and forget all the old definitions of “success”. Success is what you decide it is – whether that’s a corner office or a home office.

Just “lean in” where you’re going to be at your best most often, and be brave enough to give the new way of work a try.


[For more on the the shift toward freelancing, read The Geography of America’s Freelance Economy from the Atlantic.]


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