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  • Danielle

6 Things No One Tells You About Being Your Own Boss

Updated: Dec 15, 2022

Being your own boss

On the whole, self-employment is pretty great. It’s the sort of thing we all dream about, especially when the days at work are long and your boss is being a bit of a jerk. As with all things in life, though, working for yourself isn’t perfect. There’s a tremendous adjustment period when you first transition from your 9 to 5 to working from home. In addition, the level of responsibility absolutely does not decrease. If anything, it quadruples.

All that being said, I love being my own boss, and I would recommend it to anyone who thinks it might be right for them. Not sure if this is what you want for your career? Here are some things I’ve learned about self-employment that I think you should consider before taking the plunge.

1. You aren’t really your own boss.

Let’s be honest for a second. While there’s no micromanager standing over my shoulder, telling me what to do and when, I still have responsibilities and people who are counting on me to get projects done. In fact, I now have a large group of “bosses,” all people to whom I am accountable. The CEOs of the companies I work for are my bosses, as are my editors and project managers. These folks expect me to get work done by its due date, just like my old boss did when I had a 9 to 5. That isn’t ever going to change.

One the one hand, it’s pretty challenging to serve so many masters, so to speak. Any one client doesn’t really care what projects I have due for another company on the same day (and understandably so), which means I have to use my time very efficiently and get work done well in advance so that I don’t run into issues with deadlines. Being accountable to many bosses just means good organization is essential. I am my own micromanager now, and that’s something that’s challenging, but it works for me. I don’t pretend to think that it would work for everyone. It really depends on your personality.

2. You learn a lot, all at once.

Being self-employed isn’t just about being a writer, a photographer, or a social media manager. Before you take the leap, you may feel as if you’ve perfected your craft, whatever it is. What you may not realize is that owning a company is also about being an accountant, an IT department, and a salesperson. When you own a business, especially if you’re a sole proprietor or just starting out, you absolutely will be forced to do it all. And you know what? I think that’s fantastic. I manage my own books, file my own business taxes, fix my own computer, and send out bids for new clients. Did I know how to do any of these things before I got started? Heck no! Are these things harder than I’d like, sometimes? You’d better believe it. But just like with anything else, as I got used to my new responsibilities, they became easier. And I’m pretty pleased that I now have all these additional skills. Knowing more is never a bad thing! Entrepreneurship is a journey, and I’m looking forward to (and a little nervous about) whatever challenges come my way next.

3. Every day isn’t productive.

There are some days when I wake up without any energy whatsoever. Oftentimes, these are the days right after I pushed too hard to meet a tough deadline. Just like when you have an intense workout and suffer fatigue for the next couple of days, mental exertion takes its toll. I find this to be the case to a far greater extent now that I work from home than when I had a traditional 9 to 5 job. Sometimes, I’m pumped up, motivated, and tackle everything on my to-do list and then some. Other days, I’m dragging and close out my day feeling like a total failure.

I’ve come to realize that these ebbs and flows are normal and that I should probably get used to them. Just because I *can* make myself do anything at any time doesn’t mean it isn’t okay to have a lighter day and spend my extra time at Target and the grocery store. I just have to understand that doing so means I’ll have to buckle down the next day. So far, at least, listening to my energy levels and adjusting the day’s workload accordingly has worked for me. I always get everything done by its due date, because I have to. This flexibility is one major benefit of self-employment.

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4. Breaks are absolutely essential.

Along the same lines, it’s absolutely essential that you take frequent breaks when you work from home. I’m a fairly introverted person, but sitting in front of my computer all day does take a bit of a toll on me after awhile. I start to crave human interaction, movement, and even just noise. I try to get up frequently, even if it’s just to grab some water, start some laundry, or make a phone call. Punctuating my work periods with productive or enjoyable break periods helps me to work faster and harder when I settle back in at my laptop.

Forcing yourself to remain in front of a computer for 8 hours straight probably won’t work. Think about all of the interruptions you have during a day in most traditional office settings. Making coffee, meetings, phone calls, and talking with coworkers eat up a huge amount of time. They also give you a much-needed mental break that can help increase your productivity. You need that when you work for yourself, too.

5. Your health may suffer.

When I worked a 9 to 5, I walked about a half a mile a day just to park my car and then get to the office. I took walks at lunch whenever I could, and running errands allowed me to take frequent trips up and down the stairs. All of this activity adds up, and suddenly not having it can be a bit of shock. The possibility to sit around the house in yoga pants all day and never move from your couch may seem appealing, but believe me, it gets old fast.

If you are self-employed and work from home, you need to make an effort to incorporate activity into your workflow. Take a walk during your least productive part of the day to get the blood and inspiration flowing. At least once per half hour, stand up and stretch. Move around as often as you can. Try to squeeze in a full-blown workout as often as possible.

Nutrition is also a key part of wellness for those who are self-employed. When I worked outside of the home, I packed a lunch every day. For one thing, I’m too cheap to buy lunch, and for another, I knew this was an easy way to improve the quality of what I was eating. If I brought something with me to work, I almost always ate it. Not only was this a great way to get rid of leftovers, it practically ensured I would eat fruits and vegetables, as long as I packed them.

Now, any food in the house is fair game when it comes to lunches. While this does allow for gourmet meals, I rarely go that route. Whatever’s quickest is usually my preference, which can be dangerous. It’s harder to resist empty carbs and sweets when they’re laying around the kitchen and I am eager to get back to work as soon as possible.

If you’re self-employed, work from home, or are thinking about it, I would encourage you to force healthy food right from the start. Whatever you do, don’t let yourself eat poorly, even a little bit. It’s too easy to get sucked into bad habits that will be hard to break.

Be kind to yourself, though. Sometimes, if I’m having a particularly rough day, I’ll force myself to eat some fruit, but then I let myself have Nutella on the side. That feels like a good compromise. Maybe it will work for you, too.

6. People may not understand.

When I try to explain what I do to other people, I get a lot of blank stares. In part, this could be due to the fact that I’m not great at explaining it yet. What do I do? I write articles on every topic under the sun, I manage social media for clients in a variety of unrelated industries, I write RFP responses, and I provide strategic planning for marketing efforts. I sit at my laptop for hours and make phone calls constantly and create invoices and work on the weekends and go to the bank in the middle of the day. It’s a weird life, to be sure. I think for many people who run their own businesses, it’s hard to nail down their “elevator pitch,” so to speak, which explains in a succinct way what it is that they’re all about. It’s something I need to work on.

Also, though, some people may not understand in a way that’s a little harder to come to terms with. I promise you that when you tell your friends and family that you’re quitting your stable 9 to 5 job to work for yourself, they’ll get a bit of a nervous look on their face. Sure, it’s because they love you and don’t want you to make a mistake, one that could hurt your career or your family’s finances. It may not matter that you’ve spent months or even years planning, hustling, and getting your financial ducks in a row. It may not matter that you already do the work on the side and know it’s a financial win. It may not even matter that you’ve never been more sure about anything in your life. They care about you, so it’s only natural for them to worry.

On top of all that, some people may think that you don’t have a “real job,” or that you just spend all of your time watching daytime television and eating candy. People may accuse you of mooching off of others, like your parents or spouse. Feeling like others think your efforts are fake and that your lifestyle is being subsidized by the hardworking folks you care about? Not a good feeling. I’m not saying all of these things have happened to me, but some have, and some have happened to other entrepreneurs I know. They may happen to you, as well. It’s all just par for the course.

But here’s the simple truth. It really isn’t anyone else’s business what your plan is or how you’re going to make it work. (Except your spouse or partner, if you have one. This is absolutely something that should be a joint decision. You need their buy-in before making a major choice like striking out on your own.) This is your life, and if you believe in your ability to make something happen, you’ve planned it out, and you’ve tested the waters, you owe it to yourself to go for it.

Just like if you worked as a corporate employee, it wouldn’t be appropriate for family or friends to ask you about your income or benefits, it’s really not acceptable for the same people to ask you about your income or the specifics of how you make it work once you’re self-employed. I’m not saying they won’t. But you should feel free to tell them you’re not comfortable discussing it. Sitting back and quietly continuing to get your work done and build your business is your best bet. In time, anyone who was worried, jealous, or doubted your abilities will see that you were in fact capable of what you set out to do, and that’s all the proof you ever need to provide.

At the end of the day, working for yourself is different, but not so different, from working a 9 to 5. You still have responsibilities, though they may look a little different. You certainly have more flexibility. If I want to schedule a doctor’s appointment for noon on a Monday and it takes three hours, that’s totally fine. I may have to work until 8:00 pm to make up for it, but that’s okay. For me, the freedom to schedule my time as I see fit makes any inconvenience worthwhile.

Running your own business is no cakewalk either, but if you can put aside the day-to-day stresses and mounting paperwork and passive-aggressive criticism from your BFF who just doesn’t get it, you’ll be able to revel in the remarkable truth that you built something for yourself. Being self-employed rather than working for someone else is like owning a house instead of renting. Sure, it’s a ton of work and you won’t love it all the time, but every moment that you spend is going toward equity in YOU. That’s something no one can ever take away, and it’s something that time will surely prove to be a worthwhile decision.


Being your own boss

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