Being a Lousy Employee Made Me a Successful Entrepreneur

Restless and rebellious desk jockeys, take heart

Joe Procopio
Published in
7 min readMar 17, 2021


A young man experiencing stress after a video conference on his laptop, working from home.
Photo: MR.Cole_Photographer/Moment/Getty Images

Whenever a young person asks me how they can make a career out of being an entrepreneur, I try really hard not to disillusion them. But I feel like it’s my duty to warn them that being an entrepreneur is a terrible career choice.

Don’t get me wrong: There is nothing I would rather do with my life than start businesses, grow companies, and help and advise other entrepreneurs to build their own businesses. Being an entrepreneur makes for an awesome life — just not an awesome career.

I’ve faced a ton of challenges founding, leading, and advising companies for over 20 years, but the toughest among them is the fact that I’m this deep into the startup game still haven’t found what I’m looking for. The biggest hurdle in my entrepreneurial career is that I still don’t feel like I have a career at all.

Is this you too? Are you fighting an uphill battle explaining to friends and strangers what you do, struggling with problems and decisions no one else worries about, and maybe getting a little jealous when corporate perks are thrown at your peers?

If so, you’re not alone. Let me tell you how I discovered that walking your own path, especially when you have to create that path while you walk it, requires redefining your goals, but can ultimately wind up being the best choice you ever make.

I was that kid with the briefcase

I was not a child entrepreneur. I never so much as opened a lazy summertime lemonade stand.

When I was growing up, if you had told me that I would spend my life working for a Fortune 500 company for 40 years — with bosses to please and reports to write and big accounts to win and promotions to chase — I would have happily signed up on the spot.

I’m a second-generation American and the son of a music teacher and a nurse. My version of the American dream was filled with sharp-looking suits, palatial boardrooms, flights to big meetings, and all those accoutrements that seemed like business in the movies. I wanted all that.

Eleven months into my childhood dream job, I made…



Joe Procopio
Writer for

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at