The Truth About 4 Lies of Self-Employment

All my life (thereabouts) I wanted to be self-employed. Seriously. Even my first career dream of “rock star” is, in a manner, being self-employed. I wanted to graduate University and become a graphic designer; working for myself on cool creative projects. I even was self-employed for 5 years as a wedding photographer. I’ve been around the block.

I begin with all of this to establish that I am on your side if you are someone who is utterly set on becoming self-employed at some point in your life (whether imminently or in the future). I am speaking to you as one of you.

Having done it for 5 years and now being firmly on the other side of it (at the time of writing this, I’ve held a steady day job for 8 full months), I can say that my outlook on working for yourself has radically changed, and I think many people who dream of self-employment as the answer to all of your problems should heed this warning.

Head in the Sand

I say this with love and respect and, again, as someone who has been very guilty of this until about a year ago.

Most self-employed people I know aren’t honest with themselves about how happy they are being self-employed.

We get into this place where we feel the need to keep up this facade of being happy as a self-employed person. It was an accomplishment to become self-employed! We’d climbed the mountain (at least a little bit). We are successful! To admit being dissatisfied would be akin to waving a white flag; even if only emotionally.

Admitting you’re unhappy while self-employed feels like admitting defeat. It sort of is. And I think that’s one of the biggest reasons most self-employed people won’t do it (except for in very indirect, private ways).

Again, the below is just my experience and could easily be argued with studies and data, but if you like what I have to say, please go ahead and consider this.

Most self-employed people I know have an aversion to facing their shortcomings. They shy away from the truth when they know it’s difficult.

This is a terrible way to live your life, but it’s especially a bad way to run a business. Don’t get me wrong: choosing struggle and difficulty is against human instinct.

We avoid pain! That’s normal. It’s human nature.

Knowingly, willingly facing difficulty is not easy to do. But something about the self-employed crowd in particular seems to struggle with this more than most.

Maybe it’s because you have to have a blinders on to succeed at being self-employed; sort of a take-no-prisoners approach. In the pursuit of being self-employed, this is a gigantic asset (at least in the beginning). But it can quickly become a hindrance if you aren’t willing to ever critically, honestly analyze your satisfaction.

All of this to say: Don’t be a self-employed fool who is never honest with himself. If my argument today isn’t enough to persuade you to deeply reconsider, that’s ok! But don’t hold out on admitting things have changed, or being self-employed wasn’t all that you thought it would be.

It rarely does any good to delay doing something you know you must do.

The 4 Lies

With that warning out of the way, below are 3 of the biggest lies I believed (or was indirectly led to believe) by people who didn’t work for The Man.

Don’t read these and say to yourself, “This won’t apply to me.” It does. Especially, more so, if you don’t think you’re someone who doesn’t need to hear it.

Head in the sand, remember?

1. It will get easier

Listen, I’m not saying it’ll never get easier, I’m just saying it’s not going to get easier any time soon, and it’s definitely not going to get easier all the way around.

If you’re like me, you dreamed of self-employment because you believe you’re currently struggling. You might be right! You might be thinking, “Well, things can’t get much worse than the situation I’m in right now anyways.”

Maybe so, buddy, but I’m going to argue that trading traditional employment for self-employment is just exchanging one struggle for another. You might be better suited to handle a different struggle for a time, but don’t be mistaken: it will be a struggle. Everything will be.

Zack Arias is a photographer who said pursuing photography (substitute general self-employment for the sake of this conversation) is trading in your day-job for a day-and-night-job. Especially in the beginning, he’s absolutely right: even if you’re foolish enough to think this doesn’t apply to you.

If your new self-employed job doesn’t literally take up your evenings and weekends, it will certainly take up mental load during those times. When your business is your livelihood, and you fail or succeed solely by your own hand, you become mildly obsessed with your small business. It’s nature (and probably smart!). The stakes are a lot higher when it’s just you.

It’s not that most self-employed people don’t realize they’re volunteering for more work and less hourly pay, but it’s that they think it will be easy to manage. It isn’t; even if you’re super successful. Be prepared.

I was relatively well-established within the first year of being self-employed, and I still endured challenges—many of them different from year to year!—that made being self-employed a ton of work and stress. Two of those years were affected by COVID—that’s fair, and I hope you never have to face that as a self-employed person—but life happens and things will always interrupt our plans. Anticipate it.

2. It will give you more flexibility

This was one of the biggest draws for me to become self-employed: I wanted to be fully in charge of my own schedule.

Vacation when I want. Work when I want. Sleep when I want. Start when I want. Quit when I want.

Wrong on nearly every account.

Don’t get me wrong: you do get to set your working hours as a self-employed person—to an extent. What you eventually come to realize is the average person (thus, a large percentage of your friends more than likely) work traditional business hours: 9am to 5pm, Monday to Friday. If you want to do anything with them, anticipate it to be outside of that time window.

As someone who worked weddings, many of my Saturdays were taken up with wedding days. No big deal, I’d think, I’ll just take off the Monday for my weekend.

Even when I did that:

Know who you can hang out with on your average Monday? Not many of your friends, that’s who.

It didn’t matter that I could technically be off work, because there was nothing to do anyways. I also had a spouse who worked those traditional business hours, so it felt wrong for me to take the day off if she was going to be working a 6 day week. On top of that, there was a small mountain of work waiting for me (there always is), so it was easy to go into the office and work anyways. I wanted to, in order to “get ahead” of all the responsibility I had on my plate.

Ok, even if you find a nice weekly rhythm:

Do you know how hard it is to force yourself to take a vacation as a self-employed person?

Believe me, it’s an oxymoron.

Taking a vacation as a self-employed person is particularly difficult because, again, everything falls on you. It feels good to knock down your to-do list. Your anxiety probably builds when that list gets bigger and bigger (this, overall, is a good thing. Anxiety can be a fantastic motivator).

Self-employed people also tend to be people-pleasers (aren’t we all, in some capacity?). This means making a customer, or potential customer, wait an entire week to hear back from us becomes a really, really hard mental game to play. I know in the wedding industry, I would easily lose business if I didn’t respond to initial inquiries within 24 hours. I’d seen it happen many times. It sucked (especially in the seasons when I was desperate for anyone who would pay me—a really bad way to operate your business).

All my lofty ambitions to take weeks and weeks of vacation time every year involve an intense amount of self-discipline. Most self-employed people I know aren’t capable of it, even if they’re really self-controlled.

The last major area you lose flexibility is financially. Because every dollar your business spends comes directly out of your own personal pocket (assuming you forward all profit your business makes over to yourself), it becomes harder to spend money your business needs you to spend. Even if you can clearly articulate how and why you need it.

Flexibility as a self-employed person is a mirage on the horizon in the desert.

3. You spend 8 hours daily on your passion

The title of this is exaggerated, but only a little bit. As a non-stupid about-to-be-self-employed person, you obviously know that you won’t get to spend 8 hours a day doing only your passion. But I still think it’s probably even a lot less than you think.

Even if you never become as cynical and money-hungry as I might sound below, there’s no denying that a significant portion of your business life is now going to be spent doing the following:

• Communications with existing customers

• Marketing & sales to attract new customers

• Paying bills, tracking down late payments, bookkeeping

• Customer service when things go wrong

Passion becomes an obstacle

Want to know something even crazier? You’re going to stop seeing your passion (the whole reason you started this business) as fun, and start seeing it as an obstacle. Let me explain to you a weird paradox that happens when you become self-employed.

Photography was my passion, right? I firmly believed: the more time I get to spend with a camera in my hands, the happier I am.

Photography is one of the really rare, lucky self-employed jobs where you only ever spend 10% of your time shooting photos, and the other 90-95% of your time doing any of the following:

• Editing

• Consultations with couples

• Marketing yourself

• Answering emails

• Coordinating with clients

• Bookkeeping, accounting, paying bills, etc.

Might seem weird that I said it’s a “lucky” job to only spend 10% of the time with a camera in your hands, but let me explain.

When you become self-employed, you are desperate for cash. You literally have no income unless you have a customer giving you their money. Now, everything in your self-employed job is focused around that: getting customers to give you their money as quickly as possible so you don’t fall behind on your monthly bills.

What also happens is that anything that holds up the process of customers giving you their money is an obstacle in your path. Again, no money = no life (mortgage, food, electricity, cat).

Eventually, you become fixated on building a business where it is as easy as possible for someone to give you their money. But eventually comes the time when you have to deliver on your services (why the customer hired you in the first place). This means you have to stop doing every other aspect of running your business for X many hours as you fulfill that new customer that just paid you.

In wedding photography, this looked like many, many hours spent planning, shooting, and editing photos. You become a cog in the small-business machine you’ve created. You run out of time to be creative and flourish and interesting and over-the-top because you just need money.

You see where I’m going with all of this?

You don’t spend 8 hours a day, 40 hours a week, 50 weeks a year doing your passion. In fact, the more time you spend doing the “passion” part and not doing the “business” part means you’re losing opportunity to make money. The passion part becomes a hindrance to being paid and affording your life.

Welcome to the rat race of self-employment. Doesn’t look all that different from being traditionally employed, does it?

Hence this article.

Before I became self-employed, I really really believed that I wasn’t going to let the rat race of money dictate the way I ran my business. That was a nice ideal when I was still newly married and without kids. When I settled into self-employment and realized I wanted things in life I couldn’t afford, it quickly became my reality.

It’s not money hungry, though: I am not as obsessed with money as I realize I’m probably coming across. But you need money to survive. I was struggling to hit the bare minimum of what I considered acceptable.

4. It will make you happier

This has been the common thread through this entire article. I’m sure you’ve picked up on it.

Self-employment promises (or we promise ourselves that through self employment) you’ll be happier. No boss to report to! No one forcing you how to live your life or spend your money or operate. It’s fantastic.

Wrong again.

Every one of your customers becomes a mini-boss.

And while you can tell a couple of them to take a hike if they don’t jive with what you’re doing, you need the vast majority of them. You only have so much freedom to be picky about who you work with.

When my number was called to begin quitting self-employment, I really realized that I had been guilty of what I warned against in the beginning of this article: having my head in the sand about my happiness.

Is happiness entirely dependent on your job or circumstances? Ha! No. While I think happiness is hugely a choice you make, there is no denying that making better decisions in all areas of your life will ultimately impact your choice to be happy.

When I entered self-employment, I was (still relatively) newly married with no kids. I also had the fire in my bones to be self-employed that I wasn’t willing to give up. Fair enough! Maybe I just needed to get it out of my system.

All of these things I’ve discussed today eventually became evident to me.

I had long been lying to myself about my happiness in my job.

I stupidly prized being self-employed above a lot of other things, and when I took an honest and critical look at this unwavering belief I had, I eventually discovered just how mistaken I was. Because I now had young kids and deeply wanted to have a social life again, I knew that a traditional day job would fit better into my life, and make me (and my family) much happier.

In Summary

Am I saying all self-employment is a trap? Heck no. There are definitely people it makes sense for. And it might even make sense for you if only for a time.

Do I think reading this blog, prior to becoming self-employed, would’ve persuaded me not to do it? Probably not. And I still learned so much through the process of being self-employed that has become a gigantic asset to my traditionally-employed life now.

But it was freaking hard. And I was dishonest with myself, my friends, and my clients about how much I loved what I was doing.

Overall, the experience was a net positive, but in some ways, this is only just barely true.

Do what you gotta do. Despite how this all seems, I’m not anti-self-employment. But if you’re going to do it, at least do it with your eyes wide open. And don’t stick around too long if you start to adopt some of my revealed truths underneath the lies of self-employment.

You have an opportunity—right now—to make a more informed choice. I’m honoured you’ve read this far, and that I’ve been able to (hopefully) play a very small role in that for you.