Sharing the Real Struggles of Being a Solopreneur

I took a break from blogging for a little bit recently, and I think part of the reason why I took that break to begin with is because sometimes the grind can be… well, a grind (you’d think I would’ve known that considering I picked the damn name of this blog!!).

But seriously…

Starting and growing your own business is hard and takes a lot of effort. We all know that… or at least we all say we know it. 

But that doesn’t mean that when we’re in the thick of the grind – the part where we really have to get down-and-dirty and do the not-so-fun stuff that has to get done – it doesn’t kinda suck.

What I realized is that that’s okay, and the sooner you accept it and embrace it, the better. We see little snippets and clips online of the uber-successful and how amazing their lives are.

But we never see the late nights, the years it took to get there, the hundreds of hours spent on boring shit that they’re now outsourcing, the frustrating months where no money is coming in…

The list goes on. And we don’t see any of it.

Part of why I started this blog was to highlight these tough times because no one else does. Yes I want to share the ups and the positive lessons learned… but the real good stuff is the stuff no one talks about, which coincidentally is one of the hardest parts of solopreneurship – dealing with the boring tasks, the on-going struggles, the loneliness…

And it’s why I’m back with such a vengeance. I’m not in this to grow a huge following and monetize the crap out of it – I’m in it to share the real struggles and grind of solopreneurship, so that:

a) people who haven’t started yet can see what it’s actually like, and

b) people who are going through it know that at least there’s one other person going through the same stuff they are

Anyway, that’s why I’m back – for real – and that’s why I guarantee that I’m here to stay.

And while thinking more on why I needed said break, I started to realize that I wanted something more out of my current solopreneur business – working by myself just wasn’t cutting it.

I talk a lot about some of the downsides of solopreneurship – and a major one is loneliness. There are ways to combat this (see my vlog at the bottom of this page for one), but a simple solution is to hire people to work for you and manage (at least it is for me, because I like managing/leading).

“But Josh, then you wouldn’t be a solopreneur!” 


SG isn’t just for solopreneurs, and I also thought about a way to play a little mind trick on myself.

And that is to look at my businesses/projects as a whole… or a “company”… that I am “leading/managing”, instead of individual units of which I am the sole employee.

Let me explain.

It’s easy for me to look at my law practice (where I just have a part-time VA) and SG (where I don’t have any employees) and my new legal side project (where I don’t have any employees) and think…

“Boy, it sure is lonely working all by my lonesome on these businesses.”


What if I take a different approach, and think to myself:

“Boy, it sure is cool getting to manage these different companies/projects and making decisions for all of them!”

See the difference?

It’s small, and heck, you may think I’m borderline insane for even suggesting to think like that, but it’s made a big difference for me in the last few days. 

Now, instead of thinking of myself as a “lonely solopreneur” (I don’t think this often, but once in a while), I’m more of a business manager/leader. And with that slight shift, you start thinking more positively and looking for opportunities in a different way.

Anyway, this was a semi-ramble, but was a nice revelation for me and I think you can apply it too, even if you’re not running a business. 

Action item: think of one aspect of your business or job that you don’t love, and shift the way you think about it. Or shift the title you give it. In a positive way of course…

And see how it effects you in the mid/long term.

That’s enough of me for today – let me know if you have any thoughts or feedback and if you enjoy the content, make sure to join my email list where I send 3 emails per week with insight just like this to keep you motivated through the week!

Follow along on my business journey

Get my daily email for business tips, stories from my day-to-day, motivation and more!