The Unhappy Successful Solopreneur

The Unhappy Successful Solopreneur

If the self-help industry and generations of philosophers can’t settle on the “secret sauce” of happiness, we won’t attempt to solve that one today! Let’s just agree that…

  1. You know happiness when you feel it.
  2. You want more of it. We all do.😀
  3. One way to get more, you’ve decided, is to work for yourself.

There are, unfortunately, many unhappy solopreneurs. The most common source of that unhappiness? A lack of success.

Once unsuccessful solopreneurs resolve the sticking point, they continue on the road to success. If they don’t, they fail. Hopefully, they learn and try again.

This article covers the less talked-about, rather exotic but still fairly common “species”… the unhappy successful solopreneur.

These solopreneurs love their niche and have high traffic that monetizes well. Yet they’re stressed, tired, unsure of themselves – “unhappy,” in a word.

To understand this condition, as well as how to avoid or fix it, let’s back up and review the essence of solopreneurism. Then we’ll work forward to this not-so-rare condition.

The Multi-Hatted Solopreneur

multi-hatted-solopreneurAs a solopreneur, you do it all. We all know that the solopreneur does it all. You don’t just wear many hats. You wear them all. At times, all those hats (“tasks”) can feel rather precariously balanced!

Sure, you may contract out a logo design or the programming of a page with special functionality. It’s still you, though, who had to find and hire those specialized services.

Unless you start hiring part-time employees, you do it all. And that’s fine (for now). Wear those hats proudly!

You know all this, of course. However, few think about sorting those hats (“tasks”) into types. Doing so is key to avoiding or leaving the ranks of the Unhappy Successful Solopreneur.

According to this excellent post (in Small Business Trends)…

“Solopreneurs have an inherently entrepreneurial mindset, and they prefer single-handedly managing their business.”

The solopreneur plays a third role… the Technician. (Why call this role “Technician?” It’s explained below.) For most solopreneurs, it’s the dominant role.

Solopreneurs choose to do all the usual day-to-day tasks (content, marketing, social, email, etc.). These tasks are neither entrepreneurial nor managerial. They usually choose to do them all because they don’t want an employee, even though an employee would allow them to leverage the type of work that matters most (i.e., what they do best). But…   

They like being “solo.”

So there you have the 3 roles of the solopreneur…

  • Entrepreneur – the one with the ideas and vision, someone who wants to grow the business and who steers the ship.  
  • Manager – the person who keeps it all organized, managing operations and finances.
  • Technician – the one who carries out the “to do” tasks on a day-to-day basis; has a particular knowledge base and enjoys sharing it.

Scroll down to the bottom of the Small Business Trends post and you’ll see a smart comment & question by a woman named Karina (and a reply from us). Karina’s comment inspired this post. Here’s what she said…

“I run my own business and like many others who do this, I wear many hats and am involved in every aspect of it. However, my mom often references the book ‘The E-Myth Revisited’, insisting that I’m nothing more than a technician and a far cry from becoming an entrepreneur.

“Now that I’ve read this article, it seems that I could describe myself as a solopreneur. If you’re familiar with the E-Myth, what would be the difference between a technician and a solopreneur, since both seem to be hands-on doing most of the work themselves.”

Karina is right – solopreneurs do wear many hats. A solopreneur is the ultimate “chief cook and bottle washer!” Karina’s mom has a point, too – the most-worn hat is the technician’s.

Once your inner-entrepreneur has set the vision for the business and your inner-manager has laid out the practical steps and processes to realize the vision, they have little more to do.  What’s left is to roll up your sleeves and execute – do the necessary work.

So “Mom” only sees the Technician doing all the work. (It would be nice, though, to see a little more support from Mom! All solopreneurs need the love!❤️)

Until you achieve a certain level of success, most of your work will be done by the Technician in you. Assuming you know and love your niche, you’re going to enjoy this stage of your business development. At some point, though, a question arises…

Can you keep doing everything yourself as your business grows?

Karina mentioned The E-Myth Revisited. The book’s author, Michael Gerber, contends that you eventually need help…

If your inner-technician continues to do it all, he says, you burn out. So you hire others to do the grunt-work and you concentrate on management. Later, as your business continues to grow, you delegate management tasks to others and you concentrate on the vision and the idea-getting.

Makes sense, right? Yes, except for one small detail…

Life as a visionary entrepreneur, heading up an ever-expanding team of employees, is not for everyone. This is a much bigger role than that of the solopreneur.

You start the crossover from “solopreneur” to full-blown “entrepreneur”on the day you add your first regular payroll obligation to your expenses. You are assuming some risk in return for bigger reward. It’s an exciting time, for sure. But here comes the “but”…

It could be anathema to the very things that drew you to solopreneurism in the first place…

  • freedom to live life on your own terms
  • a love of working alone
  • escaping the hustle and bustle of big business.

“I Knew Him When He Was Poor But Happy”

There is much truth in this old business joke.

Losing sight of your life desires/values as you grow your business could turn your dream into a nightmare. For someone who truly wants to stay within the bounds of solopreneurism, pushing into EntrepreneurLand is going to prove to be too stressful.

With continued growth, each addition to the team could feel like like a prison with more walls around you. You weren’t planning on 80 hour weeks (with gusts up to 120).  Setbacks are much more stressful. What do you do with a bad hire?

On the other hand, you may discover ENTREpreneurialism is right up your alley. You may have thought you were a solopreneur. But as you grow, you start feeling more comfortable with quitting the day job, more excited about the do-ability of it all.

At some point, as you read and learn and gain experience, you realize that if you do not adjust and grow that original dream, you’re going to get bored and depressed. You hire and grow, thrive and love it!

These are both very real scenarios. On the surface, many people appear to be doing well. And, to be fair, they are doing as well as they originally wanted (in terms of financial goals).

You would be surprised, though, how often that does not translate into “happiness.” Few acquaintances will let you pierce their “happiness veil.” But trust us… until their inner “truepreneur” matches their real-world access, they may not be miserable, but neither are they happy. Your business and you must be in sync.

Quick summary of happy LIFE endings…

  1. You are reaching goals and not tempted to go for bigger prizes.
  2. You always planned for greater things and are happy to enter the realm of the entrepreneur, with all the risk and lifestyle changes that come with it.
  3. You weren’t planning on this, but upon honest self-assessment, you’re happy to carefully step onto a bigger platform.

Are you truly ready to delegate? What if the work of others is not as good as you could have done? How will you handle setbacks? Lost weekends? This is a serious jump, and few give it the full life-balance/personality inventory that the decision deserves.

Rather than discover (the hard way) that you’ve taken a seriously wrong turn, let’s discuss how to avoid and/or to cure The Successful-but-Unhappy Solopreneur Syndrome. These questions are simple but tough, which is why we call this test…

The Naked Mirror Test

The key to long-term happiness as a successful solopreneur is to stand in front of the mirror and answer a single question with naked honesty. Do this at the beginning of your new business, or do it right now if you’re well into a business and have never done this…

  • [STARTING OUT]: How big do I want to get?

Follow with this “bookend” question at the “goal-reached” stage of your journey…

  • [SUCCESS: GOAL REACHED]: Now that I’m here, am I happy to stop?

We hate to be “squares” about this (it’s “cool,” we know, to just go-go-go for the gold). But if you expect a balanced life on the road to mega, life-changing success, you’re going to be unhappy. Align business and life goals.

Let’s address each of the 2 questions at levels where most solopreneurs play…

[1) QUESTION WHEN STARTING OUT] Before you pick a niche (the answer affects your choice), ask yourself how big you want to get (income and # of employees) .  

  • Solopreneurs typically answer “$20-100,000/yr, with no regularly paid employees.” Earning more than that as a full-time solopreneur is possible, but will generally require some help. $10-20K for part-time, grow from there.

There’s nothing wrong, and everything right, about recognizing the desire for a simple life enabled by the independence bestowed by solopreneurism. Perhaps, if things are going well, you’re ready to add a part-time employee, maybe even 2.

  • Entrepreneurs have bigger answers! We’re not talking about someone who wants to be the CEO of the next Snapchat. If your goal is $150,000 (net profit) and if you’re open to adding employees, you belong here.

A true solopreneur has no problem with a target income of $20,000 (e.g., to supplement other sources). Totally do-able solo, with lots of time to enjoy life. The next question (“goal reached”) may provoke a bit more soul-searching.

If your goal was $100,000, you’ll ultimately find “pure” solopreneurism too time-consuming to do it all by yourself. There’s risk in adding even 1 part-timer, and not just financial risk.  S/he may drive you crazy, may not be as good as you thought (common), etc.

Can you fire without losing sleep for a week? Are you ready to bend a little beyond “solo”? If so, go ahead! If not sure, rethink.

Adding a regular payroll is “the transition zone.” Most people would still consider you to be a “SOLOpreneur” with 1-2 part-timers. But what matters is how YOU feel about it.

As income grows toward a higher goal, perhaps you’ve contracted someone on an “as needed” basis. You need her more and more, so that person becomes a regular part-timer. Next, you realize that, as search traffic and social media grow, adding a 2nd part-timer with the right skills will leverage business income…

“Greed” starts to trump “fear” – no judgment here – both are normal parts of the human condition.  Just be aware and be realistic as you approach the 2nd question…

[2) SUCCESS: GOAL REACHED]: Now that I’m here, am I happy to stop?

THIS is the question no one asks. How much is enough? How much will continued growth eat into the “living life” side of the equation?

Some of the happiest solopreneurs in the world are only earning $40,000-$50,000 per year, only work 30 hours per week, 40 weeks per year.  They KNOW that they never want to manage an employee or customer.  

(Some have already managed in “another life.” They are like Northern “snowbirds” who vacation south each winter, who know that if they “ever see another $#%^&@ snowflake, it will be too soon.”😜 Employees and customers are a former manager’s “snowflakes!”)

Others earn $100,000 with 2 part-timers. Some love starting every day, can’t wait to get out of bed. For others, the problems drive them crazy. Dinner is spent complaining to your spouse about the latest mistake by, or argument with, an employee. You’re distracted, wondering how to fire that person…

If you can’t get past the universal “need to be liked” and fire a poor hire, if this small level of success brings too much stress, you have your sign. Real entrepreneurs sail through this phase. Scale back (yes, you’ll have to fire somebody once) and reassess. We all have a thermostat that is set to an ideal business-life balance.

These folks will NOT be happy as entrepreneurs  STOP!

The reason few people go on to become big-time entrepreneurs is that most of us are natural solopreneurs. And the beauty of being alive today is that this route is more possible than ever. It can be a truly wonderful way to… 1) own your life, 2) earn enough (and even more than enough), AND 3) be happy.

What if you are basically happy where you are, but still want to earn more? These are the two lowest-risk, least time-consuming, and most life-preserving approaches…

  1. increase the yield from current monetization models (takes much less time to grow what you have established than to build entirely new models)
  2. use Trafeze, an excellent way to add entirely new income streams by dealing with other successful solopreneurs, at no risk (free, and takes minimal time).  More on this option…

Trafeze delivers an entirely new way to monetize both passively and actively.

It’s near-impossible for solopreneurs to build high organic (search traffic), a strong social presence AND her own product.  There are not enough hours in the day, not even with a part-time employee onboard.  That’s where Trafeze helps.

Don’t burn yourself out developing a product when building traffic takes every hour you’ve got. Find a product-seller in your niche, through Trafeze, and negotiate a win-win deal that eliminates the percentage-grabbing middleman.

Already busy with developing and delivering a product or a service (like Karina, who provides an offline service)? Use Trafeze to hook up with a compatible traffic-seller!

Learn more about how Trafeze can help your business here.

What if you want more, much more?

Some folks are naturally entrepreneurial or discover tendencies in themselves that they didn’t know they had. They tend to be younger, more outgoing, comfortable with some added risk, creative, flexible.

Our recommendation?  Be “CRITICAL,” too…

Challenge your exciting new plans. Find holes in them. Too many rush into this decision, fool themselves into believing that the next level is a slam dunk (“it’s just more of the same”).  If you can access a trusted advisor or mentor, do it now. It is not the mandate of this post to cover how to turbo-boost, merely to stream the right people to the right spots.

As long as you keep risk low and reversible (i.e., you can fire someone, can drop an idea without worrying about “face”), it is worth considering. If the ROI is also high, and if you’ve been brutally CRITICAL (i.e., you can’t find a hole), it is a path worth taking…

After all, if you have a “Retreat to Prior Position” plan, your worst-case isn’t so bad!

Karina: Mr. Pasta Catering

Let’s run through a quick a example, using our “comments friend” Karina! 😀

karinaWe don’t know Karina. But clicking through to her website from her comment tells us that she’s the chef (presumably proprietor) of an Italian catering company in Miami – Mr. Pasta Catering.

Is Mr. Pasta Catering flourishing or struggling? Is Karina happy to keep her business small (doing pretty much everything herself) or does she have bigger ambitions?

We don’t know, don’t need to! Let’s take a speculative look at how Karina (or someone just like her) might start with a hobby or passion, turn it into a business, and then grow the business to meet her goals.

NOTE: For the purposes of this example, we’ll pretend we don’t know that she has a local catering business.  If she has 1-2 part-time “as needed” chefs (friends, most likely), we would consider this to be a solopreneur operation.  If this business is basically always busy and has some full-time employees and an accountant, she is actually a “small entrepreneur.”  Again, what matters the most is how SHE feels about the business.

OK, let’s continue with “Karina the hypothetical”…

Your passion is cooking Italian food. Penne bolognese, chicken cacciatore, tiramisu…

Yum yum! 😋

You grew up in a food-loving family and trained in culinary management. You love developing your own recipes, too. Right now, though, it’s just a passion.

One day, after cursing your boss (in your mind!), you get an idea. Hey, it’s your inner-entrepreneur talking…

“Why not start a business from my hobby?”

Now your inner-manager takes control. How, precisely, do you take this idea and make it a reality? You identify 2 potential solopreneurial routes to success…

1) Start a blog or website.

Build an audience by writing about Italian food. Monetize by selling ads, site sponsorships and, for example, expensive cookery courses as an affiliate.

Passive monetization has become less rewarding over the years, but is still a viable option (read “The Solopreneur’s Manifesto”).  

To increase income beyond “the usual,” consider Trafeze – work directly with solopreneurs who sell a product or service in your niche. Deal direct. Cut out the middleman.

2) Start a local catering company (again, in “real-life,” we know Karina chose this route). You can still blog (time-permitting) and engage your audience on Facebook doing clever posts like the one Karina did last Thanksgiving…


A LOCAL service has no need to create a full-blown, content-based, Google-driven website. They attract global traffic. No matter how great the content may be and no matter how much traffic it may generate, the customers will be local.  So…

A local business should focus on local efforts… Facebook, Yelp, etc.  The website should focus on credentializing and “selling” the service, generating leads.  That said…

It’s not a great deal more work to add a blog that posts about the various types of foods they cook and that covers, with a fun and knowledgeable voice, the special jobs they have delivered (local weddings, holiday gatherings and other celebrations). It will not only help sell her service, it will also generate some local traffic through search.

A DIGITAL service is one that can be delivered “digitally” (ex., copywriting, programming, consulting).  This type of service will benefit from a niche-based content site that grows organic traffic.  There is only one problem…

It is hard to do both, deliver a service AND grow a successful website or blog.

So start with the site. Recognize that, when traffic grows, you will need to hire people to either maintain its growth or to help provide the service. You won’t have time to do both. If you are comfortable with stretching the bounds of “solo” in solopreneur, no problem.

Recognize, too, that it will take 6-12 months before your site and social presence starts to generate traffic and deliver clients. Many folks don’t want to (or can’t) wait that long. This is why so many services, digital or local (such as Karina’s offline catering service), rely on advertising (and hopefully word of mouth!) to attract customers. Each are effective, although it can take some time and money to learn how to generate strongly positive ROI.

Trafeze is an attractive new income-increasing option for service-sellers (especially “digital” ones).. Why build a high-traffic blog or website (with no assurance of success), when you could deal directly with folks who have already done it for you? Deal directly with other solopreneurs for high-value leads.

The 2 Questions

Whichever way Karina chooses to monetize her passion, website or local service, we hope she uses the 2 questions…

How big do I want to get?

Now that I’m here, am I happy to stop?

Remembering the answer to the first is like having a constant beacon. The answer considers not only income, but life itself (so easy to lose sight of).

As the business grows, her Technician works harder and harder. Hopefully, she reassesses as she reaches and passes her goal..

Now that I’m here, am I happy to stop?

Perhaps she discovers she’s happy. She likes the money. She’s happy with life. She can focus on improving the product, customer service and… enjoying life.

Perhaps she finds that she loves business-building, has exciting plans. Going through the exercises outlined previously, she decides to go for the brass ring. She can do that and prevent risk from spiralling out of control.

Done right, she relinquishes more and more “Technician work.”  She concentrates more on management as the biz grows. Then she hires a manager. Each step must be well considered and be fully prepared to reverse, re-consolidating at the previous level.

Does Karina become Il Grande Formaggio of Miami? Is life a joy? Each block, if well laid, takes work OFF her back (ex., the manager orders better mozzarella than she ever sourced and the technician slices it better!)  She’s still working hard, with more at risk, but this is the life that was meant for her (even if she didn’t know it at the time).

Or does life become one big ball of stress, even if profitable… IF it remains profitable?  This will NOT happen if the roadmap laid out here is followed, if honest self-assessment points you down the road that is right for you.

Wrapping Up

1) How Big Do I Want To Get?

The critical point, you know by now, is to link the right choice to the right person.

The entrepreneur in you will want to shoot for the stars! The solopreneur will be drawn to one of the smaller, simpler options.

Whichever choice you make, you’re right (assuming you answered the question with naked honesty). The truer you are to yourself, the smoother the ride, clearer the vision.

For most, the answer will be solopreneurism. So what if you leave (theoretical) millions on the table? Do-ability and the happiness of a simpler life are more important, right?

Your answer here is somewhat like a New Year’s Resolution. It’s made at the beginning, truly intended, but easy to forget. The next step is not to lose sight of that decision as you grow your business.

Now that you’ve reached that goal, it’s time to stand in front of that mirror again and answer the second question…

2) Now That I’m Here, Am I Happy to Stop?

If yes, terrific. Enjoy life and the fact that you’ve turned a hobby you’re passionate about into a decent-paying business (one with equity, by the way – there’s a business out there that will want to buy yours!)

Show me the money!If no, if the dollar signs are now flashing, take a breath and think about why you made the original goal to stop where you planned?  Your inner-entrepreneur will be begging, cajoling, threatening

“Go big or go home!”

The manager will be worried, but (seeing all those dollars) may underplay how much more work it’s going to take…

The poor little technician – the guy or gal who’ll actually do most of the work – needs to be strong here.  You’ve built a nice life for yourself. You’ve made it. You’re happy!  

Why jeopardize that for money.  It can’t buy happiness and you already have it!

Or perhaps that lifestyle turns out to be pretty dull now that it’s real. Recognize the “call of the entrepreneur” and go build that empire. You know you won’t be happy until you do!

Just do it as laid out above… carefully and ready to reverse. This is not TV. You’re not the next Mark Z, with millions in Venture Cap to back you. Do it right!

Some do find their true calling, after starting as solopreneurs. Some do turn out to be entrepreneurs!  You learn rapidly, have good instincts, master enough new skills, have bigger ambitions and are unafraid to lead.

Bottom line?

Do not move to a new goal that requires a version of you that cannot handle it. If you can handle it, tread carefully. This is REAL life. If you can remember that…

However you succeed, and at whatever level, you will have done it without losing the initial vision of independence, control and freedom.  You’ll also have reached it without having to become someone you’re not, without losing the work-life balance that everyone needs.

Be happy!