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Do You Want to be Self-Employed?

Prefer to listen rather than to read? This essay is also on the podcast here.

In the last several episodes I covered the six essential building blocks every small business needs to attend to. 

While it’s certainly not a crushing or melodramatic amount of work- it is a lot! 

And many of us come to self-employment through a side door. Meaning, few of us choose self-employment first, and then what it is we will do as a self-employed person second. 

Instead, most people acquire some skill, and either right away or eventually, it makes the most sense to deliver that skill as a self-employed person. 

Many of the people I work with are in the healing arts in private practice. This is also the field that I have been in for 20+ years, so I know it well! 

These types of businesses are the perfect example of training in something without there being much attention shined/shone (how do I say that??) on the fact that you are most likely to wind up being self-employed.

That means there is an additional skill set you need to acquire: the skill set of what you need to do to run your own business, no matter how tiny, in addition to training in whatever skill you are studying whether it’s manual or movement therapy, acupuncture, somatic psychotherapy or whatever it might be! 

This means that many people wind up working for themselves without ever consciously asking themselves the question, “Do I want to be self employed?” 

In order to answer that question one would have to know at least some of the outlines of what it means to be self employed. The six building blocks that I covered answers what is needed to be self-employed. 

But to answer the question of if you want to be self employed, that takes a little more digging. 

I’ve worked with hundreds of clients over the years helping them with their small business, usually a healing arts business or a coaching business, and a small percentage of these people discover at some point that hey, they don’t actually want to be self employed! Which I think is a perfectly fine choice to make! 

Oftentimes those of us who support self-employed or entrepreneurial types of businesses are caught up in cheerleading it as the best option for everyone. Usually this is because, whether consciously or unconsciously, there is an income motive at play; If you make your living helping people with self-employment, it behooves you to be positive about self-employment and to tell people it’s all super great for everyone and way way better than taking some job! 

But in this essay, it’s real talk time. 

I’ve been self-employed for 23 years. Sometimes I love and absolutely cherish it. I’m always grateful for it. 

Sometimes I question all of my life choices and can become despairing. And I know I’m not alone in this! Because I talk to many, many other people who are self-employed. Hundreds even!

I certainly can’t answer the question for you if you want to be self-employed, but I do think it’s important to at least pose the question to and for yourself. 

And I’m happy to discuss some of my own pros and cons that I cycle through in the best of times and the worst of times. 

Let’s start with the bad news, because ending on an up-note just feels better, yes? 

Con #1 to being self-employed: You have to make everything happen for you. You can’t coast, you’ve got to hustle in many different ways and attend to many different pieces of the small business puzzle. 

I remember years ago dating someone who was leaving several years of working as an employee to start his own business. One day he said to me, “When you work for yourself you do so much work for free!” I laughed because it’s the point of view of an employed person: that there is work you do that brings in money, which is paid, and work you do in the hopes of bringing in money, and this is unpaid because it might not pay off. Or work you do totally unrelated to being paid, like adding more paper to the copier. 

In part that’s because when you work for an organization, there are many people who have different assigned roles. So if it’s not your role to get more paper for the copier, there is someone else who will do that, and will get paid to do it. But you perceive that you only get paid for carrying out your role. 

But when you’re working for yourself, it’s all just part of the work. And it doesn’t always lead to income. 

Con #2: There is no safety net. This “safety net” is highly imperfect for employees as well, but it’s not nothing! Here are a few ways employed people have a safety net that self-employed folks don’t: 

First, what I was just talking about, there are other people to help out with all the work! Other people have their designated jobs, just like you, and everything goes to support the workplace. You don’t own everything! You’ve got teammates! 

This is also a “pro” for employment- you have more of a community around you. Some of the people in that community of co-workers you will like or even love, some you will dread and avoid. Humans be human-ing no matter what, right? But we can say it’s a less lonely way to work than a solopreneur business. 

Another piece of the safety net for employed people: Employer matching for your retirement savings. This is not a small deal. Also employer matching (or rather, paying into) your social security taxes. This is US specific but many other countries have their own version of this. Basically both of these boil down to more money that someone else pays to take care of Future You in retirement. 

The next piece of that safety net is A CV, or resume. When you’ve been employed you can point to your work history with “evidence” that it happened because you worked somewhere. If you’re a self-employed lifer this doesn’t matter much, but if you are popping in and out of employment, your CV is something valuable which can validate that you know what you’re doing, and that and you haven’t been secretly on the run from the law or something during those big gaps in your work history (i.e., time you spent working for yourself). 

Yet another piece of the safety net: Tax support. Surely you are paying your own taxes still, no one else is going to pay them for you. But they get automatically pulled out of your paycheck. As a self-employed person you have to remember to save a percentage of your earnings for taxes, and then to actually pay them or life will definitely be very sucky for a while. It’s a small thing, but this automation does mean one less piece of the puzzle you have to attend to.  

A final piece of the safety net from an employer: Health insurance support. This is also mostly a US thing. It also happens to be a disappearing thing, as these days people have to pay more for their monthly premium in order to have the same kinds of (crappy) coverage that I pay for myself as a self-employed person. Meaning, a plan with a higher deductable. So… this used to be a big part of the safety net benefits, but it’s a dwindling thing here in the States these days anyway. 

Con #3: (which I will also discuss separately as a pro): You don’t know how much money you’re going to make any given day, week or year. The roller coaster ride is real, and, in my experience, it evens out but never really goes away. Meaning, there are periods of being super busy and periods of being super quiet. 

Same thing goes for employed people, but they get paid the same no matter what. Whereas for us, when it’s quiet, a lot less money is coming in. This doesn’t feel awesome. 

Which means that another part of the skillset for a self-employed person is to get comfortable standing on shifting sands. The sands, they truly don’t ever really stop shifting. There are many good ways to cope with shifting sands: things like safety net savings, or dedicating a day per week to practice building so that your client flow is more consistent, or just good therapy or a good business coach who tells you, “Hey, you’ve survived quiet income periods before, you’ll survive this one too.” But guess what the solution is? More hustle! Which circles back to my first con, that you have to make everything happen for you. 

This is a real bummer way to start 2024 right!? At least you know I’m not falsely cheerleading you into running your own business?>

Ok let’s move on to the good news, the pros of self-employment. 

Pro #1: You GET to make everything happen for you. When you are an employee at a large, or even small, organization, the wheels of change turn slowly. And the organization you work for really only wants you to be the specific cog in that wheel that they hired you to be. 

But as a self-employed person, if you want to change the direction of your offering, your model for how you deliver it, your branding, your pricing, your location your… anything! You can. You have the freedom to be a lot more creative and adaptable. 

Pro #2: You don’t know how much you’re going to earn in any given day, week or year. This is a good thing as well as a bad thing. The good news side of this is that you aren’t hemmed in by the salary you were hired at, and you don’t have to beg any boss for a raise. 

Instead you can use your creativity to grow your income in a variety of ways from something as small as raising your rates, to something as large as bringing in employees to deliver the service, or adding on additional offerings. I’m not going to pretend it’s EASY to do this, but it is possible to do this. 

Pro #3: You are not at the mercy of crappy coworkers and/or bosses. Sure you don’t have teammates to help you get things done, but you also don’t have the burdens of those teammates either. You control your time, your schedule, your direction, your vision- the whole thing! 

Pro #4: Layoffs aren’t a thing. Other than, say, a once-in-a-lifetime pandemic arriving, you’re not likely to lose all of your work very suddenly. Having a client-based business is almost like having many bosses. I mean this in a good way! The support net that sustains you is spread out among many people, your many bosses, your many clients, not one “boss” or one corporation. There are definitely ways that this can make self-employment more rather than less secure than employment. 

Employees, especially those in corporate environments (as opposed to healthcare for example) have a high risk of being laid off. It’s harder to get yourself fired these days, but layoffs can always arrive. Which means that the employed people of the world are also standing on shifting sands. Projects or product lines can disappear and with it, poof! Your job! So being employed is not shfiting-sands-free, it's just shifting-sands-light. 

Now… who’s ready to homestead it with me in the woods? Let’s go! 

I’m kidding, kind of. 

But while I fantasize about building my off-grid log cabin, I’ll be here working for myself. 

There really isn’t a right or a wrong choice. There certainly is no perfect choice. Remember, especially at this time of the year, New Year’s, when most influencers are selling some foolproof path to a perfect life, that certainty, about anything, is elusive. 

And there are no right or wrong choices for everyone. Starting your own business is no more impressive or more virtuous than getting a job and vice versa. It’s really about what works best for you in this glorious, messy, imperfect world we live in. 

Give yourself permission to explore and I wish for all people to have good, integrity work that sustains them in all the different ways we need sustaining. 

Happy New Year everyone! Here’s to 2024.


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