Late Night Thoughts from a Lost Entrepreneur

Ian Greenfield
2 min readMar 11, 2022

The life of an entrepreneur is inherently lonely. At least that’s been my experience so far.

I left college because I didn’t want to be another number in a system. I didn’t want to be another business kid who went off and got meaningless job after meaningless job until I had enough money to do what I really wanted. By that point, of course, I’d be 60 and hardly have the energy for anything exciting.

Now I’m sitting here wondering if I made a mistake.

The reason people love being part of the college — graduation — job program is because it’s easy. You complete the work assigned to you and then you go home. It doesn’t matter if you’re bad, great, or anything in between. As long as you show up to the office or clock in to that Zoom call, you can expect a paycheck every other week.

That’s not the case in entrepreneurship.

You have to work for every dollar you make. And unless you’re successful, it’s hard to put your efforts on a resume. It’s hard to put “good at business” in a LinkedIn bio.

I’m sitting here at my desk absolutely fed up with the project I’ve been working on for the last several years. It’s made decent money, and I don’t regret it. I just don’t care to do it anymore.

And now I don’t know what to do.

I know that I want to start something new, but I don’t know what. And that’s the hardest part.

All I can think is I wouldn’t have this problem if I was an average joe with an average job.

But this is the life I chose, and I must carry on.

Tonight I’ll have a drink to celebrate the weekend. In my drunken dreams perhaps the answer will appear.

If not, there’s always tomorrow.



Ian Greenfield

Nashville, TN. Founder @ Shockmouse Media, a better website and design solution.