I have a fantasy where I leave my house and go to a space where all the tools to do my work are available to me – a desk that’s not tucked into a corner of my bedroom, a printer and copy machine that are always stocked and ready for use, a real recording studio instead of the pillow fort I build in my closet whenever it’s time to record a new podcast episode.
In this fantasy, not only is everything I need to do my work provided for me, but so are the tasks of the day. When I show up, there’s no agonizing over what to do because it’s already been decided for me. My job is to just do it. And at the end of each week, I get a predictable paycheck direct deposited into my bank account, along with benefits like health insurance and an employer 401k match. Maybe I even get paid when I’m sick, or better yet – on vacation!
You might be thinking this sounds a lot like a job. And you’d be right, it does, (a good job with good benefits at least.)
At a time where people are fantasizing about quitting and early retirement, my fantasy looks a lot like traditional employment.
But the thing about fantasies (in my opinion), is there’s a reason they’re fantasies.
Because on the other side of the office amenities, predictable structure and steady paycheck I dream about, is everything I can’t stand about traditional “corporate culture” – excessive meetings, onerous and arbitrary workplace policies, like those that dictate what days and hours you need to be in the office, and working with people in positions of authority that you can neither stand nor respect.
Similarly, the fantasy of self-employment has its own dark sides. And while the benefits of controlling your own time, projects and workflow can be hugely rewarding, and even worthwhile, the real challenges of being your own boss don’t seem to get nearly as much attention, which can leave many new business owners blindsided by the experience.
In short, self-employment is not for everyone
And even if it is for you, it might not be for you all of the time, depending on what other goals you have and what else is happening in your life.
So here are some of the challenging realities of self-employment I’ve learned from my own ten years of experience:
Having total control over your own time also means having total responsibility over your own time
And that’s a lot of pressure. If you’ve ever been through the process of planning a wedding or managing a home renovation, you might know that feeling when you get to the end of an exhausting day and think, I can’t possibly stand to make another decision right now.
When you’re self-employed, that’s every moment of every day. And with every choice you make, there’s the nagging thought of the 999,999 choices you could be making instead that might be better optimized. Along with the knowledge that making the wrong choice could mean the difference between hitting your revenue goals and being able to pay your bills, or not.
There is always “a boss”
Just because you work for yourself, doesn’t mean you’re not accountable to anyone. Instead of answering to a boss, as you might at your 9-5, when you’re self-employed, you’re answering to customers or clients.
Having a business is, by definition, providing a service or product that someone is willing to pay you for. So whoever that someone is, is who you are accountable to. And just like there are irrational, disrespectful and downright bad bosses, there can be all that (and more) when working with clients and customers.
You have to know your appetite for risk and uncertainty
The risk and uncertainty that comes with self-employment feels so obvious, I wasn’t even sure whether to include it. But seeing as how I’ve managed to remain successfully self-employed for a decade and still can’t predict what the next year or two, much less five years, of business and revenue will look like, I figured it was worth reiterating. It’s not like risk and uncertainty suddenly disappear once you’ve found some semblance of success.
Of course, traditional employment is not risk-free or certain either, but there is a question of scale that I think every prospective self-employed person needs to ask themselves about the level of risk and uncertainty they are willing to tolerate. Along with an assessment of their financial realities, and what they can potentially rely on to help mitigate those risks.
Having no structure can mean having no boundaries
The shift to working from home during pandemic lockdowns was a lesson for many in the slippery slope that is not having definitive spaces, structures and expectations around work.
Without the structure of the workplace to help create boundaries between what you do and the rest of your life, it’s easy for work to seep into all the places and all the hours of your day.
And while this can be true of traditional employment as well, when you’re self-employed, and the potential for greater revenue and rewards is effectively limitless, it feels exponentially easier for the time you spend thinking about work to become limitless as well (and not necessarily in a good way).
Being good at something, doesn’t mean you’ll be good at operating a business around that thing
Just because someone is a great baker or knitter or carpenter, doesn’t mean they’ll make a great bakery owner or self-employed craftsman. Because the skills that go into a particular craft or discipline, are not the same skills that go into creating, growing and running a successful business (i.e. marketing, sales, customer service, etc).
I’m personally terrible at hiring, delegating and managing operations. It’s a constant hindrance to my business that has nothing to do with the service I’m actually providing. But because it’s critical to the sustainability of my work, I have to dedicate time, resources and a lot of trial and error to doing it.
There is always more to do
This is one of those general life truths that can get amplified to what feels like infinity when you become self-employed. As can the guilt of doing absolutely nothing.
Being self-employed can be incredibly isolating
As frustrating and flawed as the workplace can be, there’s a lot of community built into it.
Before I started working for myself, I, like many other people, met my future husband at work. I had friends and acquaintances and people I’d see regularly to check-in with. And while I’m grateful for the alternative sources of community I’ve been able to find and grow for myself, it can still feel isolating when so few people understand the realities of what you do.
When you’re self-employed, creating your own support system becomes another item on your to do list that’s easy to deprioritize among the endless list of other things to get done, but it’s also essential to making self-employment sustainable in the long term.
All of this being said, working for myself has proven to be one of the most rewarding, fulfilling and exciting aspects of my life.
I speak to self-employments’ challenging realities not to dissuade anyone from pursuing their own self-employment journey, but to acknowledge the ways in which however you choose to work can be simultaneously thrilling and challenging, overwhelming and boring, rewarding and maddening, all at the same time. And it’s not a matter of one way of working being better than any other, it’s about finding a way of engaging with your work in a way that works best for you.
Thank you so much for being a supporting member of “Too Ambitious”.
For a deeper dive into some of the financial considerations of business ownership, check out this episode of the Money Confidential podcast: Is now a bad time to start a business?
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