If you recently became self-employed, you’re probably realizing just how big of a psychological toll it can take on you.
In fact, it may feel so hard you’re thinking of quitting. But hold on a second. Let me first share a few lessons I learned in my four years of freelance writing.
By the end of this post, you may discover that what feels like a struggle right now is actually an opportunity.
First things first: Even though working for yourself isn’t easy, it may still be your best bet. Especially if you want your work to be more than just a way to make money.
During the first years, the psychological strain of self-employment can drive you mad. The challenges seem to come from all sides — finding clients, filing taxes, branding, project management… The list seems never-ending and it can easily make you doubt yourself and quit — or, even worse, burn out.
But this doesn’t need to happen. You can still reap the great rewards of working for yourself, such as freedom and sense of purpose. For that, you need to get past the psychological hardship and see self-employment as so much more than just a job.
Author and business coach Barbara Winter put it this way:
“Self-employment is more than just a way to make money. I tell my clients that self-employment, with all its problems, is a great opportunity for personal growth. It’s a chance to challenge many of the beliefs that hold us back in life.”
You need to learn how to look at the challenges of self-employment as opportunities for growth, rather than existential threats. That’s what this post will help you with.
But first, I think we could do with some reassurance.
Self-Employment Comes With a Set of Challenges No One Prepared You For
A lot of people are lured into self-employment because of its shiny promises. Freedom and doing meaningful work. The ability to work whenever and from wherever you want.
These promises became cultural memes we’ve all seen on social media. A happy influencer sitting on a beach, working on their website with a colorful drink in their hand. A hyper-productive entrepreneur who accomplishes a day’s work in three hours and then spends the rest of their time playing, learning, and nurturing their family.
Who wouldn’t want to be like them?
Of course, we tend to forget that those memes don’t paint the full picture. While self-employment opens lots of doors, it also comes with its unique set of challenges. Most people only discover them after they start working for themselves — not before.
Contrary to what the self-help industry might have you believe, these challenges aren’t so much about productivity or “getting things done.” If you decide to work for yourself, chances are you already know how to deal with those — or, you’re actively learning it. Otherwise, you wouldn’t even consider this career path.
The most acute challenges of self-employment aren’t the practical ones. They’re psychological. As someone who cares enough to start your own venture, you’re probably more ambitious and sensitive than average. You want to succeed and make a difference. This usually also means that you’re inclined to overwork, take things personally, and beat yourself up when something goes wrong.
These don’t help you in any way — especially when you’re just getting started.
Even though you know this, it can be hard to change those behaviors. And there’s a lot at stake. Especially at the beginning of your self-employment venture, you can’t afford to feel down for too long.
As freelance journalist Frankie Miren put it:
“The trouble is, drumming up new work — be it pitching features or picking up fares for Uber — requires a degree of self-belief and togetherness. Drop below a certain threshold, and it all falls apart.”
Knowing that you can’t let yourself be down for too long creates immense pressure. This pressure manifests as a series of challenges that self-employed need to learn how to deal with if they are to continue on this career path successfully.
The thing is, few of us are equipped to deal with them. The education we receive usually prepares us for something else — obeying rules, meeting others’ expectations, and hitting arbitrary performance benchmarks. This can be helpful in a corporate career, where the rules of the game are clearly established.
But self-employment is different. You need to establish most of the rules you’re playing by. Setting income goals, negotiating work hours, establishing your creative process — there’s a lot of freedom in deciding all of that.
But as they say, with great freedom comes great responsibility. If your rules aren’t aligned with your core values and boundaries, you may be signing yourself up for burnout. And that’s even before you even take your new career off the ground.
How to Avoid Burnout as a Newly Self-Employed
Burnout isn’t the same as overwork. Sure, working too much can be part of the equation. But burning out often comes from doing work that doesn’t align with your values — or even actively suppresses them.
Psychologist Herbert J. Freudenberger described burnout in a way that’s particularly relevant here: “A state of fatigue or frustration brought about by devotion to a cause, way of life, or relationship that failed to produce the expected reward.”
That’s exactly what happens in the first months or years of self-employment. You become disillusioned when your fantasy about what it means to work for yourself meets reality.
Initially, you get into it because you want to do something you love. Then, you quickly realize that there’s more to following your dreams than just fun and games.
On top of practicing your beloved craft or developing world-changing products, there’s marketing, networking, pitching, and admin to do. You discover that to truly work on your terms, you first need to earn the trust of those you’re serving. Before that happens, you often need to walk a rough path for a while.
On that path, four psychological challenges arise. You need to learn how to overcome them early in your self-employment journey — or else, you’re running the risk of burning out or quitting.
Challenge #1: Seeing the Bigger Picture
When you first dive into self-employment, something big happens: You confront your dream with reality.
You finally start doing what you said you would. And that’s amazing! However, it can also be a huge shock to see how reality responds to your ideas.
Allow yourself to process that shock fully. It’s natural. You’re in a serious career transition, and transitions always contain an element of challenge. The important thing to remember at this point is this:
Just because you struggle it doesn’t mean you’re doing the wrong thing.
To know whether you’re on the right track, you’ll need to spend more time doing what you’re doing. The first months and sometimes years of self-employment are all about experimenting and learning the ropes.
As Tara Mohr points out:
“The first phase of a new venture is *not* about running a thriving business. It is about the process of figuring out what product or service is going to work out there in the world. The early years are about a kind of structured trial and error to find out what your business is going to be.”
Remembering this can lift the pressure of having it all figured out from the start. That’s not how it works — not for you, not for other self-employed folks. To understand it, you need to zoom out and see the bigger picture of the path you’re walking.
This is just the beginning of your self-employment venture. It’s only natural that it feels messy. Don’t let that discourage you from persevering and seeing what things may look like a few years from now if you just keep going.
Challenge #2: Deliberate Rest
The challenge of getting enough rest may be the number one among all self-employed, not just the newbies. Why is it psychological? When you’re the only one to decide when to work and rest, the “work” option may seem tempting regardless of how tired you are.
The logic goes like this:
If you want to achieve something, you need to hustle. Everyone has it hard in the beginning. You need to grind your teeth and push through until you “arrive on the other side,” successful and free to pursue a work-life balance.
Hustling may work short-term when you’re doing a work sprint, e.g. preparing for a product launch or jumping on a once-in-a-lifetime opportunity as a freelancer. I entered the “hustling mode” for a few weeks when writing the first draft of my book. It helped me get a lot done in a short time.
But in the long term, you usually need more rest than you think. When you work for yourself, it’s tempting to maximize the time when you’re being productive. Even when you rest, you may try to use this time to benefit your work in some way — read a relevant book, listen to a podcast, etc.
But this just makes you think you’re resting — while, really, your mind keeps orbiting around work.
The sooner you understand the importance of psychological detachment from work, the higher chances you give yourself to succeed. What use is there in being hyper-productive for a few months if you crash right after that?
Challenge #3: Having Enough Human Contact
When you work for yourself, you need to be more deliberate about relationships than ever before. In an office, water cooler conversations happen by default. In other professions, working with a team also grants you at least some human interactions.
As a self-employed, you’re at higher risk of feeling isolated and lonely. Being in charge of your schedule often comes at a cost of working alone. No matter how much you enjoy it, this can also lead to burnout. That’s because exchanging and communicating with others is a natural human need.
The way I found to deal with this challenge was by seeing myself as “in charge of my relationships,” rather than “lonely.” Remember what Barbara Winter said about self-employment being an opportunity for personal growth? This is particularly helpful in making sure you get enough human contact.
It all starts with your mindset. Rather than seeing yourself as deprived and at risk of isolation, notice that you’re now in charge of your relationships. This is how you transform a perceived threat into an opportunity. Because there are few default interactions in your self-employed life, you can now initiate the kind of relationships that you always wanted to build.
On a practical level, I’m sure you know your options: online communities, co-working spaces, after-hours meetups, or even just checking up on your neighbors. There are many possibilities to have human contact when you’re self-employed.
However, it all starts with seeing yourself as someone in charge, not the victim of your circumstances. Make that mindset shift first, and the rest will follow.
Challenge #4: Holding Yourself Accountable Without Beating Yourself Up
Here’s a revelation that took me a while to discover: There’s a difference between healthy discipline and bullying yourself.
As you’re just starting to work for yourself, this difference can be tricky to see.
When you’re self-employed, it often feels like the world revolves around you. Whether you experience success or failure seems to be entirely up to you. When something goes wrong, it’s easy to blame yourself and write it down as your lack of discipline or knowledge.
This is often an illusion. Like with everything in life, there are things you can control — but also many that you can’t. It’s important to know which are which, especially in the early years of self-employment.
Many people advise setting goals defined by your actions rather than outcomes. If you’re a writer, this can mean producing a set number of words in a day, rather than hitting a specific number of page views. The idea here is to hold yourself accountable for what you’re doing — but also, avoid beating yourself up for what you don’t control.
This is how you can know whether you’re doing your best and where there’s room for improvement. It won’t do you any good to beat yourself up for not reaching targets you have no control over. At the same time, you need personal accountability to know that you’re making those consistent “baby steps.”
With time, you learn the difference between disciplining and beating yourself up. This one is crucial if you want to avoid the trap of sabotaging your success by being too hard or too lenient on yourself.
Keep at It: Laying Your Own Path Will Reward You
According to PEW Research Center:
“Self-employed adults are significantly more satisfied with their jobs than other workers. They’re also more likely to work because they want to and not because they need a paycheck.”
This sounds like what you want, doesn’t it? Job satisfaction and a sense of purpose is why a lot of people choose self-employment. And yes, it comes with its trade-off — but that’s the case with just about anything in life.
While you may face psychological challenges that salaried workers don’t, you also have something that’s harder for them to come by.
The freedom to decide what you work on. The infinite possibilities to fulfill whatever your purpose is. The always available option to pivot and try a new approach when the old one isn’t working.
While there is a psychological price tag attached to all that, you can learn how to deal with it over time. Keep at it. Few people master self-employed in a month or even a year.
“[T]he self-employed are less likely than other workers to say they hold a job because they need the money (…). They also place a higher value on the intangible psychological benefits of working such as feeling useful and productive, and are more likely to say they are working to help “improve society.” — PEW Research Center
I don’t know about you, but feeling useful and improving society sounds like the ultimate reward to me. If that’s also what you’re looking for, don’t quit.
Self-employment may challenge you in many ways — but it also allows you to do the kind of work you wouldn’t find anywhere else. That’s because you create the rules here.
At Big Self School we know stress builds up and leads to physical symptoms, mental health disorders, and burnout. It can be hard to pinpoint why it’s happening. Take our free stress test and discover just how stressed you are.