Having played in the small business / solo consultant space for 14 years, I’ve heard a lot about the freedom and flexibility small business ownership supposedly brings.

“Supposedly” is the important part of that sentence.

Post pandemic, many people are rethinking everything. 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 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. However, I think it’s worth looking at these two goals separately, and diving into what they might look like in your business.


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

You may think 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, 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 control 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 to play golf or take that course they didn’t have time for while working in corporate, etc.

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 them.

Boundaries? What boundaries?


Over the past 14 years I have enjoyed instances of freedom and flexibility. For years I spent summers in Chicago and winters in L.A. I have traveled for months at a time because I am able to work from anywhere.

Also, I was able to clear my calendar easily when a family member had unscheduled major surgery.

What I am trying to say is freedom and flexibility are not guaranteed if you own a business. 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.

Photo by Nathan McBride on Unsplash