4 key stages you have to survive as a solopreneur

Clear those hurdles

In today’s truly distributed world, solopreneurship is an increasingly viable path to take for many. Compared to the potentially soul-crushing tedium of life in a 9-to-5 cubicle, it offers some pretty enormous advantages in terms of flexibility, freedom and control over your own destiny.

However, it’s not all beer and skittles.

The reality is that being a solopreneur means learning how to survive in what can be an incredibly harsh and unforgiving environment. The sad truth is a significant percentage of people who go down this road don’t make it to the end. Actually making a go of it involves gracefully clearing a series of tricky hurdles without falling hard along the way.

In this piece, we’ll look at four key stages all solopreneurs have to reach, then move past, in order to thrive over the long-term. Let’s take it from the top!

1. Achieving liftoff

We’ve all got that one friend who’s blathered on wistfully for years about “maybe starting my own thing” without actually doing anything about it.

‘Wantrepreneurs’ are legion, the amount of people who actually muster up the gumption to get something off the ground is substantially smaller.

To be fair, actually achieving liftoff is no trivial task. Most people don’t have the luxury of massive background funding in order to ease into their new reality. For the majority, it’s a question of working double-time alongside an existing gig until the numbers start adding up. Once you do actually scrape together enough short-term cash, you’re still facing a terrifying leap into the unknown when you decide to actually go for it full-time.

In our roundup of key stages for solopreneurs, achieving liftoff can take a surprising amount of guts, grit and time. If you’re in it, keep pushing. If you’re teetering on the edge of it, marshall your forces and prepare to step into a brave new world.

2. Focusing on survival

By the time you hit Stage Two, the die is effectively cast. There are no background gigs to fall back on, or funding “runways” stretching far into the future. You’re in this thing on your own, and there’s no going back.

In this stage, there’s one concept that dominates pretty much every second of your waking and working day — survival. Naturally, you’ll be doing your best to present a confident, assured demeanour to the people who you’re hoping will crack open their wallets. However, behind the scenes things are likely to be a lot more emotionally raw.

Throughout this period, you’re going to be scrambling to simply stay afloat. You’ll be chasing down new business, working frantically to get existing projects out the door, and trying desperately to keep all manner of background admin obligations under some sort of control while you do so.

solopreneur key stages survival
The view out of your window in Stage Two.

There’s no nice way of putting it — this stage is a long way from fun, but there’s simply no avoiding it. Get your head down, keep muscling through, and do whatever it takes to keep the lights on. One day you’ll wake up and realize you’re not consumed by a sense of creeping terror about the week or month ahead. Congratulations! You’re now at Stage Three!

3. Consolidation and organization

By this stage, you’ve achieved some sort of cruising altitude. You’ve got a reliable cashflow coming in, a stable customer or client base, and a pretty solid picture of what the next three to six months look like. It’s an enormous relief to make it to this point, but the hard work ain’t over!

In the struggle to get this far on your own, it’s likely that you’ve built up all manner of what our developer friends would call “technical debt” along the way. This is a fancy way of saying that corners have inevitably been cut somewhere. At some stage you’re going to have to deal with the consequences — this is that stage.

The first two stages are essentially successive sprints, but nobody can sprint forever.


This stage is where you start settling in for an actual marathon. It’s all about getting your ducks in a row, and nailing down proper systems and procedures to radically improve your profits and productivity.

4. Reaching your personal capacity

At this stage, you’re operating at something close to your personal capacity as a one-person operation. The good news is these days, that capacity can actually be pretty huge. The risk is that you don’t want to back yourself into a corner and end up becoming your own personal boss from hell.

solopreneur key stages capacity
The happy, sunlit uplands of Stage Four.

You’re basically going to be faced by one constant question at this stage: Do I hire or outsource?

Choose the former, and you’re essentially announcing your retirement as a solopreneur and joining the ranks of entrepreneurs proper. Choose the latter, and you can ride that thin line for quite some time to come.

There’s no one correct answer here — it’s all about discovering your personal limits, and working out how to elegantly transcend them with the help of others.

However, it’s a great place to be. Get this far and down the line, the world’s your oyster!

Navigate through these key stages of solopreneurship

Being a solopreneur is far from an easy path to take, but it offers outsized rewards for those who can handle the demands involved. Navigate your way through the key stages we’ve outlined, and you’ll join a select group of battle-hardened individuals who are truly in control of their own working world.

Let’s step through those four key stages again:

  1. Getting off the ground and actually striking out on your own.
  2. Keeping the lights on as you power through the struggle of early-stage survival.
  3. Consolidating your position and getting super-organized once you’re over the initial hump.
  4. Considering how to scale once you hit the limits of your personal capacity.

Are you currently climbing this particular mountain? Get in touch via the comments section below and share your story!

Image by: National Library of Australia Commons via Visual Hunt / No known copyright restrictions

Tom Ewer
Tom Ewer is a freelance writer, online entrepreneur, and the founder of Leaving Work Behind and WordCandy. He has been obsessed with WordPress since he first laid eyes on it, and has been writing educational and informative content for WordPress users since 2011. When he's not running his businesses, you're likely to find him outdoors somewhere – as far away from a screen as possible!