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11 Reasons Personal Service Solopreneurs Are On The Struggle Bus

Listen to the audio version. 👆


Running a business is hard, no matter how you slice it.

But, the challenges for personal service solopreneurs are particularly interesting. They’re often more intertwined with who they are as a person versus logistical or technical challenges for a lot of other businesses.

The cool thing is that most challenges are one side of the same coin—they can be turned into something that makes you extraordinary.

The rest—well, knowledge is power. Once you know what the problem is, you can manage it.

You really freaking love what you do

It doesn’t feel like work most of the time. You chose to offer this service because you love what you do.

Even on the hard days, it’s simply a mountain to conquer; when you do, there’s the high that comes with it.

I fucking did it.

The line between work and play gets blurry.

When things are going well, it’s fun, and you want to keep doing it—to ride that feeling forever.

When things aren’t going well, you’re stressed because you want to keep getting to do what you love.

Because your line of work and non-work is blurry, you struggle to shut down the business part of your brain occasionally, making burnout imminent.

You can’t be available 24/7, but you try anyway

There’s a lot of pressure to be constantly available. People have been spoiled with 24/7 customer service and Amazon deliveries within 2 hours in some areas.

Because of that, you’re probably -

  • Responding to messages, social media comments, and returning emails during your 3 am trip to the bathroom

  • Feeling anxious if you don’t have your phone on you in case you’re needed

  • Have notifications on for every app so you can respond immediately

  • Even your off days include checking on everything

  • You tell people, “I can be reached by my cell in an emergency”

  • You consider everything an emergency

This is no way to live. And yet, you feel the pressure to respond in 3.47 seconds because if you don’t, you may upset a customer or lose an opportunity.

Or, at least, that’s how it feels.

Projecting “We” Instead of “Me”

Solopreneurs do this funny thing - they use “we” language on their websites, marketing, and other collateral when, in reality, it’s just “me.”

We do this for the same reason a three-year-old is desperate to pick their own clothes—we want to feel like a big kid. And I say “we” because I’ve done this, too.

There’s this insecurity that me, myself, and I are not enough. We want to look like a bigger business, and in our heads, that means having a team.

Instead of making us look like big kids, we shoot ourselves in the foot by giving customers the expectation that they can expect the same service from us as from a business with staff.

A comic called Ditcherville by Jonathan Stark joking about the "me" versus "we" concept.

Hiring help isn’t always a solution

Running a business entirely on your own is an epic amount of work. People truly can’t appreciate what it takes until they’ve had to do it themselves.

Of course, you’d love to offload tasks that you hate, aren’t great at, or don’t have time for.

I’m sure you’ve considered it but have felt like -

  1. Hiring, managing, and training a team sounds like a nightmare

  2. It’s too overwhelming to figure out

  3. Being responsible for other’s income is scary AF

  4. You’ve tried, and it was a dumpster fire

  5. You’re not quite busy enough to hire help yet

  6. You feel like you can’t afford it

As nice as it would be to share the burden, it’s not always an option for everyone.

You can’t be A+ at everything - but try to be

You’re amazing at the service you provide, without question.

But the chances that you’re also great at marketing, networking, writing, coaching, communicating, social media, and everything else that usually goes into a business is pretty much impossible.

In an effort to do what your competition is doing to stay competitive, you end up taking on tasks that aren’t in your zone of genius. Now you’re stressed to the gills trying to do what you’re competition is doing and also creating a poor customer experience because it isn’t your thing.

Valuing services is hard

Selling a product is easier. Buy my product, and it does X.

It’s tangible and often easier to identify and sell the benefits.

When you offer services, it’s a lot harder.

  1. You make it look easy so customers don’t value it as much

  2. It feels easy to you, so you don’t value it as much and under charge

  3. When you undercharge, it also makes customers not value it as much

  4. You struggle to identify and sell the benefits that matter to your customers

  5. You hear “It’s too expensive” or “I can’t afford it” from customers a lot

Valuing your services is both technically and emotionally hard.

Real and perceived service quality varies

When you offer a product, you have a machine that can consistently create great doodads.

With services, there’s always a degree of unknown that you have to contend with.

  • You might have a bad day, leading to a less-than-stellar service.

  • Every situation is different, meaning you have to improvise or do something differently than you normally would

  • There are outside factors that you can’t always control

  • A customer’s frame of reference for your service impacts perceived quality

This is simply part of the package of delivering a service, but something that adds yet another layer of difficulty to contend with.

The Identity Crisis

We all dream of being the go-to person for something.

When you finally become known for being the person, it’s easy to let it become your identity in and outside of work.

You can get stuck in a box and then when you have to change things, it creates an identity crisis.

It can make you question yourself and the value you bring.

These identity crises can make it difficult to make decisions and ultimately hold you back from growth.

STORYTIME: The Quickie Queen

Not long ago, I was known for being “The Quickie Queen.”

(Not like that, you dirty birdy.)

I was given this nickname because it appeared I was omnipresent. Some thought I was two different people because of how quickly I responded, no matter the time of day, and with all of the things I did.

It felt great to be known for being there for people fast.

Until it caught up with me, and I had a major panic attack because of the pressure of being there so fast and being “on” all of the time.

I had to make a lot of changes, including taking everything off my phone and keeping everything work-related to my computer.

I struggled for a bit to let go of my former identity. If I wasn’t known for that, what good was I?

Of course, I have, and had, more to offer than just being the first to respond and help. But letting go of that aspect of my identity was hard.

But you know what’s funny? The world didn’t end when I stopped responding within 60 seconds. No one hated me all of a sudden. I am still respected and appreciated for what I bring to the table.

Our brains can be real jerks sometimes.

The push and pull of Imposter Syndrome + Ego

It can feel like you have a split personality sometimes.

On one hand, you’re constantly battling Imposter Syndrome.

  • You way over prepare so customers think you have your shit together

  • When you do a great job, you contribute it to other factors

  • You feel like all of your competition is better than you, so why try?

  • Good reviews and referrals, while good, make you squirmy

Then, on the other hand…

  • Getting a questionable refund request can spark instant rage

  • When a customer questions your expertise, you feel offended (Excuse me, just who do you think you are??)

  • When a competitor charges more and seems busier, jealousy and criticism kicks in

  • When a potential customer doesn’t “get” your service or says you charge too much, you think they’re dumb

Finding the balance between being humble and open to feedback, while also knowing you’re good at what you do, and charging appropriately for it is a constant struggle.

Conventional business advice isn’t for you

There’s a lot of great business advice out there.

But most of it doesn’t share the nuances and who it’s really for.

It’s frustrating to go through the effort of reading books, listening to podcasts, and learning new skills, only to have it fall flat.

It makes you think you’re not doing it right when, in reality, the advice given just doesn’t apply to you.

Big Heart + Worry Wart

When you really care about people, running a business is extra hard.

You say yes to things you later regret or resent.

You accept less money because someone says they can’t afford it.

You give more than what was paid for.

You change the way you work to accommodate others.

Part of it is that you just love taking care of people, even if it’s at your own expense. There’s joy in it.

The other part is that you hate confrontation; you worry about what people might think about you or that they’ll leave a bad review.

Finding the balance between taking great care of people without hurting yourself or your business feels like you’re walking a tightrope made of dental floss.


Of course, not every person will experience all of these, but they’re by far the most common issues I’ve seen after working with personal service solopreneurs over the years.

Some of them aren’t even issues - but really wonderful things that can make you a better business owner. It’s just a matter of putting things like having a big heart in their proper place so you win along with your customers.


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