Ray J. Green

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TT#022 - 3 ways to end up overworked & underpaid as a solopreneur…

The first version of the online "business" I built for myself sucked.

Actually, it wasn't really a business. It was a way of earning a living as an executive freelancer. 

Chasing clients and work.

Taking what I could get.

Relying on third-party platforms for clients. Trying to capture any & all the work I could when there were windfalls... because who knew when the next drought was going to come?

It sucked.



I was on a revenue rollercoaster, had no real plan, and was still so busy building other people's dreams that I was only slightly closer to building my own. 


It’s just as common to burn out being a solopreneur as it is being an employee. 

I see it all the time.

"I left my 9-5 to go out on my own but am working harder than I was before, and making less…  and thinking about going back."

If this resonates at all, know this:

  1. You aren't alone. The road to success is very rarely a straight line for solopreneurs.

  2. There's a way out. Most of the mistakes that cause this are avoidable and reversible.

I'm going to share 3 mistakes I see solopreneurs making all the time so you can stop or avoid making them yourself. (Note: I made each of these myself when I was starting out, too.)

#1. Marketing yourself for clients like you did for employment.


A broad list of strengths and experiences may impress a potential employer, but it doesn't have the same effect on a prospective client.

Employers tend to think they're buying all your working time (hence, "full-time"), and like to think they can keep you around as long as you can add value.

When you showcase a broad list of strengths and experiences, it represents more ways to use the time they bought. That reduces the risk of hiring you. 

So, it’s best to show potential employers everything you can do. 

Clients, on the other hand, tend to want a problem solved.

When you demonstrate that you can solve that specific problem better and faster than anyone else, the more confidence they'll have that it gets done right. That reduces the risk of hiring you (and increases the amount you can charge). 

So, it’s best to show prospective clients the one thing you do best. 

Clients won't frown on the fact that you're "well rounded" with a lot of strengths. But do you really care if your mechanic can fix your bike, too?

Show prospective clients you can solve their specific problem.

#2. Putting tactics ahead of strategy.


Tactics follow strategy. My mentor drilled this into my head so often that I swear it's tattooed somewhere on my brain.

When I talk to solopreneurs interested in my coaching program, about 83%* of the questions I get asked are tactical.

  • Questions about what tools, tech, and resources to be using.

  • Questions about copy, headlines, and other messaging.

  • Questions about sales processes and scripting.

  • And more...

But most of the time, the people asking these questions aren't crystal clear on strategic things like their vision for the business, how they are positioning themselves in a crowded market, or even what they are selling. 

Determining how to do something is a lot easier when you’re clear on what you want done (and why). 

Clarify your vision, positioning, and offer before you get bogged down in "how" to sell it.


#3. Not asking for help (because you’re supposed to be the expert).


If you're going solo after a successful run in the corporate world, you may be reluctant to admit you need help. 

There are 2 reasons for that:

  1. The corporate world punished you for not having all the answers, so you created a habit of "figuring it out on your own."
    You may even be proud of this, as was I when I started. But DIY-ing your way through the process is slow, expensive, and painful. No one that matters is going to judge you for being smart enough to buy other people's experiences.

  2. The services you're selling require you to be seen as an expert, and you feel like a fraud not having answers.
    I was guilty of this. And I see it a lot from people who built & grew businesses in their careers, too. The thing is, marketing and selling yourself as a "product" is unlike any other business. Plus, objectivity is part of the value you offer clients... and it's part of the value someone else can offer you. 


Don't let fear, or your ego, slow you down, or keep you from achieving your goals.

If any of these sound like mistakes you've made or are making, don't sweat it...

Course correct, plow forward, and consider it part of the tuition for getting to be your own boss.

* The 83% statistic above is from How I Met Your Mother’s Barney Stinson. If you know, you know.