Believing These 5 Myths About Solopreneurs Is Holding You Back

It’s one thing to be held back from pursuing your dreams because of some very real risks and a sincere fear of the unknown. It’s another thing altogether to be held back by false assumptions.

How myths start is a topic for another day, but I think a good deal of misinformation is spread, if not created, by those who need to reconcile their own fears with some sort of external validation. And so the narrative changes from, “I’m afraid to do this because”, to “No reasonable person would do this because”. Fools rush in where angels fear to tread.

But that’s just one perspective. Gathering more perspectives can allow you to see something you were missing before.  Everyone has the power to write their own story. And if you’re writing your own story, wouldn’t you want to be the hero?

It’s important to be realistic when considering whether solopreneurship is right for you. Leave your rose-colored glasses on the desk and take a clear look around you.  Just don’t forget that also means having enough perspective to rise above the naysayers and fearmongers.

These are some of the more common ideas about solopreneurship that I’ve heard, but have never really experienced in my career as a solo.

1. Solopreneurs don’t make enough money

Not all solopreneurs fit the ‘starving artist’ category, though some probably do. And of course how much money is “enough” differs by geographic location, personal needs, and lifestyle choices. But that much is true whether you’re self-employed or other-employed.

One thing I know for sure – a salary is an earning cap. Even with an annual increase, and taking into account performance bonuses, there is a set maximum amount of money that you can earn every year.

As a solopreneur, your earning potential isn’t predetermined. As long as you continue to generate value, you continue to make money.

2. Solopreneurs are always desperate for work

Nope. I suppose if you’re perptually lazy and a committed procrastinator, this will indeed become a self-fulfilling prophecy.

But many of the solos that I know end up referring work to trusted colleagues, because they have more than they can handle.

Now, that’s not going to be the case when you first start out. But once you’re established, and if you’re engaged in your business, you can build a customer base and can have consistent work year over year.

3. Solopreneurs go through long stretches of unemeployment

Maybe? I have no idea. For example, in the last 12 years, I’ve had two dry spells. One where I decided to take a couple of months off and just enjoy the summer. The second was self-imposed as well, when I decided to devote all of my energy into building a software startup company. During that time, my solo business took a backseat.

Aside from these two exceptions, I’ve always had consistent streams of income. The volume of that income fluctuated of course; some months are extremely busy, others are a bit leaner. But I’ve always been able to cover my expenses.

4. Solopreneurs are sales and marketing experts

I suppose there are solopreneurs out there who definitely fall into this group, especially those solos who are experienced marketeters who have transitioned into a solo career advising other solos how to market their own businesses.

But for many of us, sales and marketing are parts of the job that were completely new and uncomfortable for us when we launched our solo careers. We learn as we go, and we improve as we grow.

I’m still very much a novice in this area, and I’m constantly looking for learning opportunities and ways to improve my skills. Luckily, customer satisfaction and referrals still count for a lot in business!

5. Solopreneurs are just getting by until they can find a ‘real’ job

None of the solos I know, myself included, would give it up by choice.

Going back to a life spent working for someone else just isn’t a scenario I can even imagine at this point in time. Maybe that will change in the future? But at this point, being a solopreneur isn’t just what I do; it’s who I am.

And that may very well have been the tipping point. When I first started working for myself, for the first few years, I did wonder whether I could continue to make a living like this, or whether I would be better off – safer, more secure – returning to the fold and working for a large corporation.

I never pulled the trigger, because every time it crossed my mind, what inevitably followed was a flood of memories recalling everything that I hated about that world. The amount of conformity required; the micro-management; the politics; the biases; having my work hours dictated by someone else; not having a choice in work assignments; being at the mercy of corporate quarterly targets that I had zero influence on; and the cubicle farms. Rows and columns of tiny gray boxes stuffed with human captives for 8+ hours a day. Ugh.

So as scared as I was of the future, I couldn’t bring myself to return to the past.

And then, as happens, time meandered on. Two years turned into four years which turned into six years. And by the time I hit that 5-6 year mark, I started to realize that I wasn’t just “lucky”. Yes, luck sometimes played a part.  But to be successfully self-employed for that long meant that I was also capable of pulling off this solopreneurship stuff. Imagine my surprise! Introverted, a complete lack of sales skills, no safety net, and yet I was able to find customers and generate income.

I slowly started to realize that I was actually good at my job. And my job was my business. And my business was completely integrated with my life.

Being a solopreneur isn’t my 9-5 job. It’s who I am.

And I wouldn’t have it any other way.



We All Dream of Someday


What Does Your Someday Look Like?

Someday. It’s the best day ever.

When are you going to quit that job you hate? Someday.

When will you will start taking better care of yourself? Someday.

When will you start doing what you always dreamed of doing? Someday.

When will you stop putting yourself last? Someday.

Someday is beautiful.

Full of promise, untouched by reality.

Someday is mythical.

It exists in our hopes, our dreams, and even, unfortunately, our best intentions.

One of the inescapable outcomes of suffering a loss is realizing just how ethereal someday is.

Planning for someday is a pleasurable indulgence, but a dangerous addiction. Constantly deferring today’s action to tomorrow’s promise tends to have a predictable and sad outcome. Plans never actioned, dreams never realized.

If I had waited until someday to start my own business, I’d still be working for someone else. I’d still be slaving away to make someone else’s dreams come true.

Sometimes we need some motivation to get started, and sometimes life gives us just the kick in the ass that we need. Other times, we need to find that motivation for ourselves. And the best way to so is to take a hard look at someday. Not just what it is, but when it is.

I’ve touched on this in a previous post (If Time Were Diamonds). Every now and then it’s good to reconcile your someday self with your current self. Take stock. Get real. And nothing is more real than realizing exactly how little time you have to get from here to there.

Don’t stop dreaming, and hoping, and planning. But stop waiting. Start doing. What do you want? Figure that out first. Sure, it could change in five years, but as of this moment in time, what do you want?

Now go get it.


Time Stopped, But Just For Me

If someone had suggested to me a month ago that I could take a few weeks off, without planning it, just disappear one day and not return for several weeks, I would have laughed in their face. Are you kidding? Spontaneously walk away from my work, from my business, from my clients and committments, for almost a month? Insane! I have so much to do, so much to juggle, so many people counting on me, there’s no way I could possibly shut it all down on a moment’s notice.

Then my father died.

And that’s exactly what I did.

I didn’t think about it, at all, of course. My dad was sick, and then he died, and then arrangements needed to be made, and there were things to do, and people to tell, and an obituary to write, and a funeral to be planned. There were pictures to go through, and clothes to be packed away, and memories to be remembered.

It never once occurred to me that the world did not in fact stop spinning. That work continued, without me. That time passed, without my notice.

But it did. And once again, I’m struck with enormous gratitude that I’m a solopreneur. That I wasn’t constrained by the limited number of bereavement days a corporation determined was appropriate for my grief.

And how immensely thankful I am that I was able to take the time I needed to take, without severe professional consequences. That I had a safety net that I could rely on when I needed it most. That no matter how busy I am, I can pause, prioritize, and re-set.

Life goes on, it always will. But how comforting to know that I can occasionally stop time, when I need to.

Making The Switch From Employee to Solopreneur, Part 1

By far, the most frequent questions asked of me, professionally, have to do with making the switch from employee to solopreneur. Or from employee to contractor, or freelancer, or entrepreneur, or self-employed, and so on. Whatever your perspective. It transcends demographics, industries, skills, and experience levels. People at every age and stage of their life, in a variety of careers, are inquiring about leaving the world of employment to strike out on their own.

In fact, I know so many people who are thinking of making the switch from employee to solopreneur, or independent contractor, or freelancer, that I often think the world of employment is on the brink of being decimated by mass resignations of the workforce any day now.

Of course, that’s not even close to reality. For a couple of reasons.

Employees – No Longer First Choice?

First, corporations aren’t desperately seeking to hold onto their employees these days. In fact, the trend is just the opposite. Organizations are looking for contractors and freelancers more often as a means to get the job done. (Intuit 2020 Report: 20 Trends That Will Shape The Next Decade) The world economy continues to shift more toward a “gig” economy, where resources are hired to deliver tasks and projects, rather than hired to fulfill the role of “employee of company x”. In many situations, this is a less expensive option for organizations, even though contractor rates on the surface seem high in comparison to employee salaries. But beneath the surface, it’s the associated expenses related to staffing employees that drive companies to engage “per project” resources more frequently. Employee benefits, paid time off, sick leave, overtime pay, on-boarding investment, professional development and training costs, off-boarding investment, and more add significant bloat to the salary line item. With contractors and freelancers, what you see is what you get. Work is estimated, budgeted, contracted, delivered, and paid for. The end.

The Courage to Change

Second, of the many people who are thinking of making the switch from employee to solopreneur, most will fail to pull the trigger. It’s not so much that they’ll fail at their attempt, it’s that they won’t even try. A small tragedy, really, for those who have the desire and likely the capability, but simply lack the courage to realize their dreams. On the other hand, for those of us who pulled the trigger years ago and make our day-to-day living as solopreneurs or contractors, we needn’t ever really worry about a flooded market. There will always be just enough fear to hold back just enough people.

At the same time, a few will certainly dare to take the leap, and so I’ve decided that the next few posts are for them. Or for you, if you count yourself among them. There are all kinds of “how to” and “tips and tricks” posts out there on the interwebs which can give some great tactical examples of steps to take to make this transition. For my part, I’d like to focus on sharing some thoughts and experiences about what it’s really like to live without a pay-check. Because all of those people who are to afraid to pull the trigger? Well, they have a point. It’s terrifying.



One Compelling Reason To Be Your Own Boss

Be Your Own BossI’ve been primarily a solopreneur for over a decade, with a brief venture into entrepreneurship that didn’t end well.

But when my startup company died a horrible death, it was ultimately solopreneurship that I turned to for comfort. Solopreneurship was my safety net.

Yet I know so many people unhappily working for someone else, wishing that they worked for themselves, but too afraid to pull the ripcord. Because they view any situation other than employment as risky.

Be your own boss?  Sounds great, you say.  But too risky.  Then why do people do it?  Are they just wild-and-crazy show-me-a-plane-and-I’ll-jump-out-of-it risk takers?

How Do You Define Risk

Solopreneurship, self-employment, freelancing, entrepreneurship, e-commerce ventures, any ventures you can think of, are so often deemed risky or not secure.

There’s no ‘safety net’ of a pay-check every two weeks.

That dependable pay-check that provides you with just enough money to get you through the next two weeks and so on and so on.

But hey that’s ok, because the pay-checks keep coming right?  Until they don’t.

Until the big company you work for is bought by another bigger company that doesn’t need little ol’ you.  Happened to me.

Or until you piss off your boss.  I’ve done this.

Or criticize the wrong bad idea.  I’ve done this too.

Or dare to suggest a better way of doing something that somebody thinks is absolutely just fine thankyouverymuch.  Me again.

One Compelling Reason

Solopreneurship, self-employment, freelancing, entrepreneurship, e-commerce ventures all have one significant common theme.  In each of these situations, the person with the most control and the most influence over your success or your failure is YOU.

In a choice between handing over control of my professional and income-generating life to a complete stranger, or owning it myself, I’ll always choose to own it myself.  Who’s my boss?  I am.

If Time Were Diamonds

Time DiamondsI recently re-discovered an article that I wrote where I contemplated how projects would be managed differently if time were treated as diamonds.  And really, why shouldn’t time be treated like diamonds?  Both are non-renewable resources, limited in supply, and high in demand.

The sparkle and shine of a diamond conveys its immediate value. But what about time?

We spend it, waste it, use it, and lose it so often without as much as a second thought. How often do you stop and think, am I really making the most of this day?  Hour?  Minute?

Seasons for a Reason

I was reflecting not too long ago on how much I enjoy the change of the seasons. Every winter I lament not being fortunate enough to live somewhere that’s perpetually sunny and warm all year long.  California dreaming?

But those moments pass, usually when the winds change and winter melts into spring.  There are four seasons, but I’m only in love with one of them.  Summer.  Of course.  I love summer.  Summer is the perfect season.  But I don’t know that I would appreciate it as much if I could take it for granted.  The changing of seasons reminds me of the finite nature of time.  It somehow gives me that sense of urgency that I sometimes need to keep moving forward.

Calculate Your Time Diamonds

Here’s something to contemplate this weekend.  How old are you now?  How long will you live?  Take a wild guess, or just use the typical life expectancy age for where you live.  So now you have the likely maximum number of years you have left in this world.  And for the sake of this discussion, let’s leave aside whether or not you believe in worlds other than this one, and whatever grand plans you may have for that.

Now, every year has four seasons.  Even if it’s sunny all year where you live, the earth continues to rotate along, changing its relative position to the sun, and therefore, changing seasons. So now pick a season.  Pick your favorite season.

There’s one last item to factor in.  And it’s an important one.  Because do you really want to count all of the years that you have left to live, or just the good ones?  Ok, the good ones and the mediocre ones.  But let’s lob off any years that are spent in pain, fear, confusion, anguish, or any other terrible outcomes from any generally debilitating illness.  Aging isn’t for the weak.

With my family history and general luck profile, I project that I have a better than average chance of developing Alzheimer’s, Cancer, Diabetes, Arthritis, Heart Disease, or some stellar combination of all five.  Do I really want to count however many months or years of deterioration in my overall runway of time left?  No.

So here’s the formula:

[Guesstimated Age at Death]


[Current Age]


[Years You’d Have Been Better Off Dead]


Number of [Favorite Season] seasons left

How does that number look to you?  Looks really low to me.  How many summers do you have left?  20?  30?  40?

Maybe you’re lucky enough to have a 50 or 60.  Still.  Pretty small number.

To make things even worse, we can’t really depend upon that Guesstimated Age at Death number, can we?  The universe likes to pull the rug out from under us when we least expect it.  But that gets too depressing, so let’s stick with our chosen numbers.

Those are your diamonds. One diamond per instance of favorite season that you have left in your bank.

How will you choose to spend your time diamonds?