7 Small Business Owners on What It’s Really Like Working for Themselves

7 Small Business Owners on the Hardest Part About Working for Themselves

I often find myself romanticizing the idea of being a business owner. I like the vague idea of being the boss and doing my job on my own terms at all times. In fact, my parents are both entirely self-employed, and watching them live full lives in which they only have to answer to themselves is inspiring, and often makes me want the same thing for myself. However, I’m also often reminded that there are many not-so-glamorous sides of owning a business and being the boss of yourself. I really shouldn’t have to be reminded that these exist — I failed hilariously at my Etsy shop endeavors (which I would write more on, but it is hard to, because it really was so short-lived).

But even though that “business” obviously blew up in my face, it only fueled my curiosity about working entirely for myself. To feed my need for more knowledge on the topic, I got nosy and picked the brains of a few small-business owners in my life and asked them to tell me what they honestly feel is the hardest part about working for themselves. Here’s what they had to admit. (Take some notes if you ever want to take the plunge and start your own business — I think they gave some good advice!)


1. “Building the foundation of a small business is really hard. It starts small, and sometimes it stays pretty small, but it does grow. Eventually, any business is going to have at least a few more people involved in it. So you have to make rules, establish some sort of protocol or mission for how things get done and what the point of the whole business is. It is weird when you start something and then you bring new people in and need to delegate tasks to them, and you need to figure out how to make them think something is as important as you do. People need a reason to say ‘yes, I’ll do this thing this way’ and it is your job as a small business owner to give them that reason.” – Sam


2. “The hardest part for us I think was definitely taking the plunge, and actually doing it. My husband and I took a leap of faith, and we just went for it! We quit our secure jobs and focused solely on this company, and honestly, I feel that is the hardest part. Not too many people have the drive or whatever to dive into it. We are taking every day step-by-step, but it’s been a great ride. And if it doesn’t work out, I will regret nothing. I’d rather try and fail than not and never know.” – Ashley


3. “For me, the hardest part is figuring out the financial side of it. I know my business, I know how to create the product and stuff, but it is hard to figure out taxes and stuff and make sure everything is in order so you don’t get in trouble. I made a lot of money when I very first started and felt really good about it, but then I realized I needed to pay taxes. I was like, ughhhh. I felt like I lost everything. It’s weird. You need to be so diligent about setting aside money for that, and not just putting it all away and thinking it’s all yours to keep.” – Joe


4. “Holding yourself accountable for everything is really hard. It was so easy when things got f*cked up at my previous job to be like, oh, it was my stupid boss’ fault, or blame any company problems on the higher-ups who are supposed to keep a good handle on everything. When something gets messed up with my business, I am really at fault because I’m the higher-up who’s supposed to be watching over everything and making sure nothing slips through the cracks. It’s just me here trying to make it all happen – no one to blame. I have to take so much responsibility, and it’s kind of terrifying that when shit goes down it is all kind of on me to accept responsibility and try to fix it.” – Haley


5. “Honestly, the hardest part is making myself do shit when I don’t want to. It is entirely my business; it runs on my will to run it every day. It’s so tempting to do nothing on days when I feel lazy because I’m the only person I have to answer to. You have to be extremely motivated and disciplined.” – Erin


6. “The hardest part I learned about working for myself was to learn to pay myself appropriately. At first it’s hard to compartmentalize yourself from your business. At first, I would hear someone’s budget for a project, and I would work with them as a friend to make it work for that price, even if it meant paying myself much less than I originally intended. Your time is valuable and important, so you need to set rates and prices and stick to them. It is hard to learn that it is okay to say no to a client. Doing it respectively is equally important. You need to really know your worth and not let people take advantage of your services just because you are their friend.” – Thomas


7. “I think the hardest part is probably just achieving any sort of healthy balance between work and your personal life. When you are a business owner, it maybe starts as a hobby, and when you figure how to profit off of it, it sort of takes over and becomes your entire life, because you like to do it but it’s also your work. But even if you own a business that you feel passionate about, it’s important to keep some sort of balance and distance between work and personal time. All of your down time can’t be spent focusing on work. You need to find a way to combat that tendency, because it’s easy to fall into. Especially if you run your business from your home. Running a business is always stressful, and even if it’s a huge part of your life and you love it, you need to separate it from your down time if you want to be a sane human. Taking breaks from work is so important, and so hard when you don’t get to leave your business in the hands of a boss when you go home at night.” – Aidan

Featured image via WOCInTech Chat

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