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10 things I’ve learned after one year of working for myself

One year ago, I made the decision to leave my full-time job and start my own web design business. Being my own boss had always been my dream, but the time just never felt right to take that leap.

The thought of waking up whenever I want, setting my own schedule, not answering to anybody… I mean, who wouldn’t want that?

That’s a completely naïve way of looking at it, I know that now. And while it may not be a 100% accurate view of life as a freelancer, it isn’t completely untrue either.

It seems as though every single day I learn something new about myself, and about running a business. And while my freelancing career may be completely different from the career you’d like to pursue, I want to share with you some of the most important things I’ve learned over the past year in hopes that just maybe it can help you out on your journey.


1. There is never a perfect time.

“What if I fall? But oh, my darling, what if you fly!”

I have that quote on a plaque right above my desk, and it’s one of my favorite quotes in the world. Before I went off on my own, I was waiting for all of the stars to align. I wanted to limit the amount of risk involved to essentially guarantee that I’d be okay.

But life doesn’t work like that.

There’s a huge risk in leaving a steady paycheck to dive into the pool of uncertainty that is starting your own business. But that’s part of the thrill! We get so caught up focusing on how poorly things could go that we forget to think about how incredible it could all be! My thought was always “what if I lose a bunch of money? I’m going to regret leaving my job.” But I never thought, “what if this goes incredibly well and I get to live my dream?”

Maybe the day will come when it just feels right. That’s when you need to go for it. Because if you’re waiting around for everything to be perfect, you’re never going to do it.


2. It’s not always about getting an immediate return.

When I first got started, I read countless articles in hopes of learning everything there is to know about freelancing. One reoccurring theme was that you should NEVER work for free. Basically, you need to value yourself and your time more than that.

Well, spoiler alert, I did not follow that advice.

Look, everyone needs to get paid. If I did free work for everybody, I’d be on the streets right now. But when I was starting out, providing free work to certain people helped to set the framework of my business! By providing work for free in the beginning, I was able to build my portfolio and my reputation. The ongoing work that set me up for is worth way more than whatever the paycheck was that I would have collected.

I don’t suggest working for free for just anyone. If you’re a personal trainer, you don’t need to train your cousin’s best friend because you feel bad. But if you have the opportunity to work with somebody that you know has a lot of connections in the industry and can help you to network, it’s certainly not a bad idea!


3. Social media, when used correctly, can be incredibly valuable.

I love Instagram, I’m just not great at it. At the time of writing this, I don’t even have 1,000 followers.

That being said, with the small amount of followers I do have, I have actually been able to make a difference. I post whenever inspiration strikes, and I’ll post anything from fitness motivation, to nutrition tips, to memes. Maybe a few hundred people see every post, but I’ve had countless people message me either thanking me for a specific post, or telling me that they really enjoy my work.

Believe it or not, I’ve even had a few clients find me through Instagram. Not by marketing, but by engaging with the community.

I can’t imagine how that would be amplified with 10K+ followers. But having just one person reach out to me and thank me is enough to keep me going.


4. You can’t be afraid to admit when you do not know how to do something.

A year ago, I thought I knew everything. I wanted to promise the world to my clients. If something came up in a project that I was unfamiliar with, I would take to Google and spend hours upon hours trying to figure it out. In same cases, that’s not a bad thing. I mean, that’s how I’ve learned most of what I do as a self-taught designer.

However, when it’s something miniscule that is not going to make or break a project, it is not worth 8+ hours of research and stress. Too many projects for me have unfolded this way. If you don’t know how to do something, there is no shame is saying so. Be amazing at what you do know, and be willing to ask for help from others if needed.


5. Confidence is important, even if you’re faking it.

I’m an incredibly introverted and humbled person. I do not like to brag about myself. I workout almost every single day to look as good as I can, and I still feel uncomfortable if someone asks me to flex. Working on it, though.

When I began my career as a freelancer, I was landing projects with not much evidence to back up my claims. Sure, I was always confident in my ability to do great work, but how can you assure someone that paying you will be worth their while?

Turns out that confidence goes a very long way. It’s the reason why some people out there can charge 6 figures for their services. Are they that much better than everyone else? Maybe not. But they are confident enough in their work that they charge what they know is fair for their services, and if a client can’t afford it, they move on.

Don’t get me wrong, I know it’s not all about confidence. But when you quote someone $5,000 and you end up doing a project for $500, there is a serious lack of confidence there. If you don’t value yourself, nobody else will.


6. Stay on top of your bookkeeping. And your taxes.

Taxes were the last thing I thought about when starting my business. I only knew life as a full-time employee, where taxes were automatically taken out every paycheck, and when tax season rolled around the government sent me free money.

Things are a little bit different now.

There are a ton of resources out there, and I suggest making sure you have a firm grasp on what you’ll have to pay to make sure you set enough aside. That $20,000 you just received is going to look a hell of a lot lighter once you have to pay your taxes. Side note, odds are you’re going to have to pay estimated quarterly taxes. To be honest, I had no idea these even existed, but I had to pay a fine for not filing them last year!

Also, make sure you track all of your business expenses. I was surprised at the amount of deductibles I was able to claim, but disappointed that I didn’t have everything on record. Business lunches, gas, software… it’s all deductible! Make sure you keep records.


7. Utilizing your contacts and resources is pivotal.

Maybe it was a pride thing, but I did not want to ask for help a year ago. I was determined to build my business on my own.

Well, what I didn’t realize is that life is all about who you know! I had heard that before, but never taken it seriously.

It’s true. Don’t be too proud to ask for help.

Take to Facebook and let your network know that you are starting your own business. You’ll be amazed at how many people either need your services, know someone who does, or can help in some way. I even reached out to somebody I interned with in High School, and they are now in a high position at a large company with countless connections. If I never reached out, I never would have known, let alone gotten the introductions!


8. Making your own schedule is pretty damn amazing. 

Everything I learned this past year isn’t necessarily some deep lesson. Working on my own schedule might just be my favorite part of it all.

If you like waking up at 7, getting ready, commuting to work, working 9-5, sitting in traffic on the way home, eating dinner, then doing it all over again… then good for you I suppose.

I love my mornings, so I still wake up early. But I go to the gym and enjoy my breakfast before beginning work between 10-11am. If it’s a beautiful day outside, I can work outside or take a mid-day break to enjoy the weather. Sometimes I’ll do minimal work during the day, and then sit down and do the majority of my work in the evening instead.

Some days I may need to hop on the phone with a client at 9am or 8pm, or commute to a meeting in the middle of the day. But for the most part, I can start and stop as many times as I want throughout the day, because I am not “on the clock”. I set deadlines, and I work in the most efficient way possible for me to hit those deadlines.

Working for 8 hours straight quickly burns me out. I need to work in intervals of a few hours. And being my own boss allows me to do just that. Plus, I have unlimited vacation days. Not bad.


9. You spend a lot of time doing the annoying work.

When you have a “real” job, you get to focus on whatever it is you do best. Designing, teaching, leading, training, etc. Sometimes you may have other tasks assigned to you that you are not excited about, but for the most part, you get to do what you’re best at.

When you work for yourself, you need to handle everything. Marketing, cold calling, bookkeeping, taxes, follow-ups, proposals, contracts…the list goes on. Looking back on the past year, I probably spent more time doing “everything else” than I did actually designing.

Luckily, it’s all good stuff (except the tax part). Cold calling and marketing eventually lead to new clients. Proposals and contracts mean you’re fostering a new relationship. It’s all time consuming and not the most fun, but it all leads to doing what I love most, and to me that is worth it!


10. Not every month is going to be great.

I had a great month last year, and I felt on top of the world. But because of that, I became really complacent and stopped pursuing new work. As you could guess, what followed was my worst month. I still made enough to pay my bills, but significantly less than I’d want to make in order to earn a living.

When you work for yourself, you need to expect that some months are just not going to be amazing. There’s no steady paycheck here. You might earn next to nothing one month, but then the next month make 10X that amount.

For me, it’s all part of the thrill. I know a lot of people would rather have a guaranteed, steady paycheck, and I totally respect that. I love that my success and failures all ride on my shoulders. I have nobody to blame but myself if I underperform. And if I do, it motivates me to do better.



I don’t have all the answers. In the grand scheme of things, a year is not a long time. But based on just how much I’ve learned and grown over the past year, I am SUPER excited about what’s to come.

I finally feel like this is a sustainable career, and one that I will be able to hold for the rest of my life.

If you’re on the fence about going off on your own, or need some advice, I’m always here to listen. Feel free to shoot me a message or leave a comment below!


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About Matt Rosenman

With over 15 years of experience in health and fitness, Matt Rosenman is the expert voice behind Matt’s philosophy is simple: no foods are off-limits, and a healthy lifestyle shouldn't be complicated or restrictive. As a former certified personal trainer with a bachelor’s degree in Health Behavioral Sciences, Matt brings well-rounded expertise to his blog. From revamping classic recipes with a nutritious twist to breaking down fast food menus, his goal is make healthy living less confusing for everyone. Featured in major publications and with a strong following on social media, Matt is committed to making “healthy” uncomplicated—no matter where you are in your health journey. Join Matt on his mission to simplify health without sacrificing flavor. Learn More