The Lonely Solopreneur

April 01, 2026

Hello my friend,

Going solo can be tough.

I have often confused working for myself with freedom.

Your own schedule and your own decisions, all requiring little or no input from anyone else.

Not being controlled or demanded from elsewhere.

Being your own boss.

Doing things your way.

Getting to live life on your terms.

(Whatever that actually means)

But here is the thing.

It comes at a price.

It has for me.

Deep down I’ve missed and craved community.

I started my own wellbeing group “Running Minds” for this very reason.

To bring people and professionals together to share, to support and inspire one another.

But I learned this was just the tipping point for me.

It made me realise what I have been missing.

Being a freelancer, small business owner, solopreneur, or whatever you want to call it, comes with plenty of challenges and downsides.

Everyone knows it must be challenging but not many know about the loneliness that comes with it.

Unless they have done it themselves.

The feeling of managing every moving part of the business wheel yourself often feels like you’re running into the wind.

The feeling of being accountable only to yourself.

The feeling of the wins and the losses only shared with yourself.

I worked in the corporate world throughout most of my 20’s.

Working 8 until 5, plus a commute.

Much of that time it paid well and offered good benefits.

On finishing university, like everyone else, it felt the most sensible and practical next step for me.

To be earning consistently and with opportunities to keep earning more.

To be on the ladder.

To put on a suit, get a company car and be in the race.

It was fun for a while.

Until it wasn’t.

I changed jobs a few times and did quite well financially but I remember vividly thinking this wasn’t for me in the long term.

But maybe I was just naïve.

I did everything I could to start a side business to escape the boardroom and office desk.

But now almost a decade later I’m seeing things differently.

I’m starting to miss parts of it.

Perhaps I have been too harsh on the 8-5 corporate world.

Not necessarily the work itself but what it can offer you.

A team, colleagues, some community.

A structure and routine.

Knowing when you’ll start and when you’ll finish (most of the time).

Earning a regular salary with some bonuses and the odd pat on the back thrown in.

I had all of the above.

Since stepping out of the corporate world I have built a wall between myself and it.

Trying to do all I can to avoid going back and working for someone else.

But that has been ignorance.

I haven’t considered both sides fairly.

There is no doubt that there is much upside in working for yourself.

But I would be lying all these years in, if I wasn’t honest about the downsides.

And ignoring the upsides of working with a company.

Ignoring the trade-off and price that is paid.

A price, quite frankly, that I hardly hear anyone talk about.

The feeling of loneliness.

Going it alone.

The lack of accountability from elsewhere.

No one to share the wins with, or to lean on during the losses.

Motivating yourself constantly.

No one knowing if you fall completely flat on your face.

Then on top all the uncertainty of income, clients, taxes and the future of the business itself.

I am writing this from a place of being somewhere in the middle right now.

Assessing my own options.

Not pretending I have it all figured out.

Still questioning parts of myself.

Still figuring out where to pour all my energy.

Into my business or into a different direction.

Perhaps towards one I knew well before.

The feeling of giving up is hard.

Stepping out of something I’ve built with love.

But at the same time being ignorant is hard.

Maybe it’s not giving up at all.

Maybe it’s looking ahead with a bigger vision to have a greater impact.

Maybe it’s a shorter term change for a longer term gain.

Or maybe it’s holding on just a little longer.

Maybe it’s burning the boats.

I don’t have the answers.

Here I am after all these years working for myself and all the fears and uncertainty are still there.

But now the loneliness feels like it weighs more.

Who knows what will come next.

But what I do know is to keep an open mind and to stay optimistic.

That has always served me well.

Trust that the right way will present itself.

Maybe you’re in a similar situation.

Trying to figure out your own path either as a business owner or working in a company.

Either way I am super curious to hear from you.

What is your story?

What has worked for you?

What advice would you share?

Share a comment or message me directly. I would love to hear from you.

Thank you for reading.

With Love, Nick x

Photo of a recent Running Minds meet up.

Grateful for this community! :)

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