When I was younger, I always found myself saying things like “Ugh, I never want a boss — I want to work for myself!” only to be met with a hearty LOL from both of my self-employed parents. They had to remind me (quite often) that the perks of answering to no one but yourself sometimes come along with responsibilities that someone like myself (scattered, not great at organization, highly forgetful) may not do well with.
In any case, I’m still into the idea. I have a mix of jobs where I work for myself and work for other people, and I see the benefit of both working scenarios. But I decided to dig a little deeper and ask some of my most successful self-employed pals to tell me some of their secrets — the good, the bad, and the stressful.
I asked nine self-employed people what their most important work-secrets are — here’s what they had to say.
1. “You have to have a ‘boss’ alter ego to whip yourself into shape when you try to get lazy. It is sooo tempting to let yourself take a long break or a day off on a day you’re feeling blah and lazy just because you’re the boss and have that liberty. But obviously, you should usually not do that. You have to be strong enough to be able to say something like like ‘no employee me, boss me says you have to keep working.’” — Janey
2. “The biggest ‘secret’ I have is just that you have to try a lot harder to separate work from personal life. I think it is often more difficult to be self-employed than when I was working under an employer (I work in construction) because there is no way for me to clock out and go home and show back up tomorrow and do what I’m told. The whole business and the office and all of the planning is all inside my head — I can’t clock out from it at night, so it is hard to stop thinking about what I have to get done the next morning. But I guess it can be that way for many other jobs, too — whether or not you’re self-employed.” — Andrew
3. “I’m a writer and freelancer, and the weird thing I’ve found is that people don’t often believe it is legitimate. I’m like, I have an LLC! Lol. But really, one thing I’ve found difficult since I’ve been working for myself is that people have a tendency to not really believe your job is real, or make the assumption that you have no structured work schedule and are just sitting on your ass all day. But I’m like, no, I work for myself and I work mostly from my home, but I also earn a full-time income and have a savings account and pay taxes and own the house I’m ‘sitting on my ass’ working all day in. So it is legitimate, and sometimes I think people who do what I do need an extra little layer of confidence to navigate the inevitable questions they’ll be asked a million times about what their job is.” — Jill
4. “You have to remind yourself (often) that your chosen path may have resulted in a pay cut at the expense of offering you other perks, like flexibility and freedom and other liberties. I make significantly less even years after switching from a corporate design job to freelance, and obviously I don’t get benefits. But those obviously-financial perks were replaced with other ones, like flexibility with hours, ability to take on more or less work to allow for personal matters to take priority or to earn more money in a given month by taking on more work if I choose to, etc. it is not equal if I compare the two jobs dollar for dollar, but personally for me, the benefits of my self-employment beat out my old benefits, like steadily higher salary and group health insurance.” — Clare
5. “I started a business dog sitting, walking, and grooming a few years ago because I worked at a local pet store as a groomer and eventually realized I knew enough people who would still use my services if I left and started on my own. I knew I just could do it in a more efficient way and generally just have a different business practice than this giant chain store’s small grooming department.
So a lot of people definitely thought it was kind of childish, like ‘oh, dog walking is what 16-year-olds do during the summer for extra cash.’ But I did actually pick up a lot of momentum right away and have done really well for myself and expanded a lot. For me, the most difficult part is that it is so easy to overextend. One of the perks about not working out of a shop and scheduling my own appointments with clients is that I can be flexible for people, but I need to also keep balance between my work and personal life and sometimes I do have to say ‘sorry, I can’t dog-sit on that weekend because I have important plans’ or ‘I can’t actually make any grooming appointments after 6 PM’ because I need to keep some boundaries, especially because I do it out of my house.” — Jacqueline
6. “I don’t feel like I have a lot of security, which is really hard. I have to find the work myself and make it happen, and if it doesn’t happen one week or one month, that’s money I won’t have to pay bills that month. I’ve never come to that point, but the point is, it is super important to just be so careful with money and always keep a buffer and emergency fund and everything. You have to be super prepared for the worst, but hopefully, the worst will never happen. You need that extra bit of security when you know there is no guarantee of work, and no employer to be in charge of making sure the work is there for you.” — Daniel
7. “My advice to everyone considering a career change and moving towards being self-employed is this: get an accountant straight away. You may think you can keep up with everything, but you can’t. You will need help figuring out your money –- you’ll definitely be grateful during tax season when you’re trying to make sure you pay the right amount so you don’t get in trouble, but also that you’re paying the least you possibly have to. Save your receipts, get an accountant, and generally just stay organized as fuck with your business-money more so than anything else, or else your personal-life money will be screwed too.” — Erin
8. “You have to have compassion, and it is great to be in charge and be able to make moral and ethical decisions you feel good about. However, you also have to bear in mind that your business is also your livelihood and how you feed your family. Bending the rules, giving financial breaks to people who can’t easily afford your services, etc. are nice things to do, but you also need to sometimes put your foot down and take care of yourself and your business so it can stay afloat.” — Alexa
9. “I will say this — there seems to be a lot of talk now amongst younger people about how the ideal life is to work for oneself and have the ability to create your hours, have a flexible schedule to allow for travel and other personal activities, etc. And I think it is really nice that people want to create that kind of lifestyle for themselves. But the thing I have to say to a lot of people who are seeking a ‘carefree’ life as their own boss is that, at least for a while, their lives might actually be a little bit more difficult. Starting your own business and working enough to make something of it and to earn an actual living off of it takes work that can’t be accomplished by working 9-to-5 shifts — it’ll take way more time than that for a while. You’ll really have to put in the hours to build the kind of life for yourself that affords flexibility and frequent travel, whether or not you are working for a boss or for yourself. The type of time and effort required to start your own business endeavor is so taxing that if you’re doing it for the sole purpose of having a flexible, travel-friendly lifestyle, it may not happen for you. You usually need to have pretty great passion about what you’re doing to make it into something real.” — Jake
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