The Loneliness, the Self-Doubt, and the Fear of Failure

The Dark Side of Entrepreneurship

Getting real about the struggles behind the highlights

Marshall Hargrave
4 min readDec 4, 2023


An illustration of the dark side of entrepreneurship.

From the outside, entrepreneurship seems glamorous. You get to be your own boss, do meaningful work, and unlock financial freedom. Who wouldn’t want that life?

But what they don’t show you on social media are the dark moments. The crippling loneliness, the constant self-doubt, and the fear of complete failure.

After years of building my business, I’ve experienced the highs and lows of this path. Here’s my honest look at the unpretty side of entrepreneurship.

You Feel Like You’re on an Island

When I first started my company, I was running on passion and excitement. I was convinced my idea would change the world.

What I didn’t realize was how isolating this journey would become. I had no colleagues to bounce ideas off or grab lunch with. No one truly understood the stress I faced.

My work was a solo venture, yet it consumed my entire existence. I had little time or energy left for family and friends.

I started declining social invitations because I needed to work. I could never relax or be fully present — my mind was always stressed about my business.

This took a toll on my relationships and mental health. I felt increasingly alone and unsupported.

Like an island, I was surrounded by people yet felt totally disconnected. No one could truly relate to my daily founder struggles. I questioned if this effort was worth feeling so cut off from humanity.

The isolation nearly broke me. I never felt more alone than when it was 3am and I was stressed about payroll making my stomach turn.

You Constantly Doubt Yourself

Being solely responsible for a business means constantly second-guessing yourself. Every decision from your product offering to your marketing approach feels monumental.



Marshall Hargrave

Serial entrepreneur. Finance, startups, investing. Catalyst-focused, event-driven. Hip-hop vigilante. On the quest for the best hot chicken.