I am a big fan of working for yourself, but not for the most obvious reasons. If you have never tried it, I want to share with you some of the most rewarding and challenging things self employment makes possible.
In this post I will use the word business or self-employment interchangeably to refer to any type of structure you create to work for yourself, whether you freelance, work as a solopreneur, build a business that relies on contractors, have business partners, or grow an enterprise with many employees.
While there are important differences between these approaches, some things are true across the board once you take the leap. That’s what I want to talk about today.
Here are 10 things no one tells you about working for yourself.
1. Relationships are different
The biggest open secret of working for yourself vs. as an employee is the relationships you build. When you work with clients, there is a feeling of equality, freedom, sometimes being part of a shared community. I have found that some of my most long lasting professional relationships built on mutual respect and support were possible exactly because of the different dynamics that are only present when doing business, and not possible inside a company.
As an employee the feelings are different because the whole set up is different. First of all, your entire income and benefits depend on one company. Often there is a hierarchy at work and power dynamics that existed for years before you even joined. If you do not cultivate a mindset of self responsibility and abundance, you can easily fall into scarcity mentality, fear, or feeling disempowered.
Of course it doesn’t have to be that way at all: healthy work environments foster mutual respect, open communication, empowerment, stability, and a sense of being supported in one’s growth, helping you create long lasting professional relationships.
But when you work for yourself it’s a lot easier to create such dynamics because as a self employed individual you simply have to take full responsibility for your experience and what you accomplish. You cannot default on negative patterns, blame the boss, or look for another job if you don’t like the environment.
2. You have to put in the time
Is it possible to grow a multi million dollar business? Yes
Is it possible to create a business with great income and work life balance? Yes
Is it possible to go on vacation, work part time, and still make plenty of money? Yes
But you probably will not get there by taking an online course that promises that you will make 6 or 7 figures in a matter of weeks running a business a few hours a week from the beach.
Building a long lasting, sustainable, rewarding business takes time, can be messy, comes with plenty of challenges, and requires you to grow as a person. You might get to the dream life you want - working on the beach and all - but you will first have to do the work.
There is no magic formula, otherwise we would all be millionaires working very little!
So plan to love what you do day to day, enjoy growing your business, and play full out to achieve your goals.
3. Freedom comes with responsibility
I love this post by Seth Godin, it perfectly captures this point: we often imagine that working for ourselves is a way to be free and do whatever we want. In reality, having that sort of freedom requires taking responsibility for your day, your decisions, your finances, and your choices.
Do I feel much freer working for myself? Yes! But I had to learn how to be in charge of my own life, business, and time. That is what gave me freedom.
Repurpose Your Purpose is not my first business, so everything was a little bit easier. But the first time I truly went into business for myself, learning to properly schedule my day and finding self motivation to do the things I had to do (rather than relying on outside pressure) was definitely something I had to learn!
Having your own business can give you a lot of freedom…but only if you learn to cultivate and take on responsibility.
4. You will come up against all your issues
Which brings me to the next point: the moment you get in business for yourself, you come face to face with all your hang-ups and fears.
Are you afraid of expressing yourself? Negotiating pay? Setting boundaries? Taking risks? Networking? Saying No? It all becomes unavoidable once you take the leap into self employment. The only way is through.
The good news? This is exactly why I am such a fan of working for yourself: it is one of the most powerful things you can do to grow.
The other good news? It never stops: the longer you stay in business, the deeper and more rewarding the journey.
This is why I have been working with my coach for many years now and I have no intention to stop. I also have an accountability buddy, and I am part of two communities of fellow coaches/practitioners. If you want to be in business and stay in business, one of the best investments you can make is working with a coach.
5. It can be harder to unplug
When the buck stops with you, it can be hard to unplug. Even if you turn off your computer, your mind can be thinking about your business 24/7. The idea of closing shop, going home, and not thinking about it until the next day (or until Monday) can at first seem impossible.
Having been in business for a long time, I can tell you it is possible to rest and not have your mind on work so much - but it takes some learning (and a lot of unlearning).
This is another one of those things about working for yourself that are either worth it to you or make you realize that you much prefer having a boss who gets to be ultimately responsible for the company.
6. You need to plan for your tax bill now. No, really.
If you are used to working as an employee, you have simply no idea how to handle your taxes as a self employed person. This is not my area of expertise (and it would take way longer than a bullet point to cover it anyway), so the best advice I can give you is to get an accountant. Now.
Not when you make more money, not closer to tax season, not after you try to do your taxes yourself. As soon as you go into business - including as soon as you start freelancing - start looking for an accountant. If you can get a referral, that’s even better.
I don’t know anyone who didn’t underestimate their tax bill as a newly self employed professional, so do not wait. Start planning for it now.
7. There are many ways to create a business
I am very passionate about alternative ways of doing business, approaches to operate outside of the traditional greedy, hierarchical, and sometimes inhumane way business is often talked about in the mainstream.
Many amazing individuals and companies are working on creating profitable businesses - large, and small - that value human beings and the planet. From B-corps to workers owned coops, from the circular economy to local initiatives, there are a lot of ways people are coming together to change the way we think about and create wealth. It’s exciting, and it’s only the beginning.
8. You have to be willing to learn (and enjoy) sales and marketing
Contrary to what some experts will tell you, you cannot have a business and not learn about sales and marketing. These are two areas you need to understand before you can delegate. Especially if you want to run a small operation - for example if you are a solopreneur, only work with contractors, or want to hire a very small number of employees - you have to understand how your business works.
And key to your business success is how you find clients (or how clients find you) and how you sell your products or services.
There are no shortcuts. You have to take the time to lean in and learn.
After you get a good sense of what your business is all about and how it generates income, then you can choose what and how to delegate.
9. Your perspective on leadership shifts
Do this: start a business and hire someone to do some work for you. And see how fast you realize how blind you were to what your boss was really looking for and going through.
As employees we are bombarded by social media content designed to make us feel like it's an us vs. them world. While this is true in some work situations, it’s not always the case.
When you experience hiring someone for your own business, you quickly become aware of both how hard it is to lead and also how difficult it is to deal with contractors or employees if they are mostly focused on what’s in it for them, and do not understand what you need from a bigger picture perspective.
Expanding your perspective often makes a huge difference if you ever then choose to go back to corporate.
This is also why I consider any business experience a win-win situation: whenever I have seen friends go back to full time employment after trying having their own business, I saw them rise up the ranks much faster, negotiate better pay, and step it up in a number of other ways. Why? Because as a self employed individual you learn it’s up to you. And you understand the big picture, including the stresses and challenges of those at the top.
This shift in awareness also makes you recognize red flags and leave unhealthy environments much faster: you know how important it is for leaders to work on themselves and can tell if that commitment is not there.
10. It’s a personality thing
Ultimately whether you prefer working for yourself or as a full time employee is a bit of a personality thing: the happiest entrepreneurs love working for themselves.
Sometimes they are making way more than they used to and sometimes they had to take a significant pay cut to work for themselves. But regardless, they just love being self employed so much, the challenges are worth it.
You either love the freedom and responsibility that come with self employment, the challenges of having to grow, pivot, and make choices, or you are so stressed out that you realize you much prefer working for someone else - and gain new insights and appreciation for it.
There is no right or wrong, it’s your journey. Get to know yourself, try things out, and enjoy living your best life. Now.
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