Self-knowledge is the key to success and happiness, at least as far as I’m concerned.

Having played in the small business / solo consultant space for eight years, I’ve heard a lot about the freedom and flexibility that small business ownership supposedly brings.

“Supposedly” being the important part of that sentence.

I have had a few prospect calls recently where I found myself trying to talk people out of starting a business. With all the nonsense in the business ecosystem these days about entrepreneurship being the greatest and best way to work, many people who probably shouldn’t start businesses are considering throwing themselves into the abyss of business ownership.

(If this is you, please go read Carol Roth’s book The Entrepreneur Equation right now.)

I have no issue with professionals wanting freedom and flexibility. I do too, if I am honest. However, I think it’s worth looking at these two desires separately, and diving into what it might mean for you.


Carol and I love our work, but we always say running a business is hard, and we don’t sugarcoat it.

You may think that being your own boss is great, and it can be – but you also may feel that your clients, vendors, contractors, and employees get to boss you around.

Is freedom possible? With strong boundaries and strategies / processes and support in place, you might be able to achieve it – or you might not.


Flexibility might be easier to achieve. You can take control of your schedule and the clients you choose to work with.

If there’s a market need, you can choose the type of work you want to do, and often when you want to do it.

Flexibility is possible. That said, please know that it’s not easy to create.

I have heard so many stories about entrepreneurs who started their businesses with flexibility as a goal, but then didn’t carve out the time to take Fridays off and play golf or take that course or do self-care.

Owning a business will suck as much of your time as you are willing to devote to it.

The to-do list never seems to go down and there’s always more you could do – more training, reading, networking, etc.

And let’s not forget the social media black hole.

In fact, there are a million ways your business responsibilities will overflow into your personal life if you let it.

Boundaries? What boundaries?


If some company would pay me to do what I do with my own business, I would go back to corporate in a heartbeat. People are surprised when they hear me say this. Unfortunately, the only way I seem to be able to do my best work is as a solo consultant.

Over the past eight years I have had instances of freedom and flexibility. I used to winter in L.A. and work remotely. Yesterday I was able to clear my calendar because a family member was having unscheduled surgery.

What I am trying to point out is that this freedom and flexibility are not guaranteed if you own your own business.

The truth is that it’s a little squishy, and pretty much everyone I know struggles with setting and keeping boundaries between their business and personal lives, which clearly impacts freedom and flexibility.

In short, it’s complicated.