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5 Important Lessons I Learned in 5 Years of Freelancing

I jumped headfirst into the freelance world at the end of 2017, but I had been freelancing since college several years before. I learn more every day and each new client, goal and calendar year brings a new set of challenges that always turn into valuable lessons. It's not an easy life, but it allows me to keep my most precious asset:freedom. I can work when, where and how much I want. It comes with a host of positives and negatives, but it's been worth it to me, and it's allowed me to see and do things I never thought possible.

If you're considering the life of a freelancer, check out some of the biggest lessons I've learned over the past five years.

1. Set working hours that work for you.

Structure is crucial. Flexibility too. When you're just starting out, it's tempting to test the limits of the flexible working day:wake up a little later; meet a friend for a long lunch in the park; opt for a nap after lunch. These are all wonderful things that become available when you work from home and have the ability to set your own schedule. For some, the reverse is true. You may be afraid of becoming complacent. Maybe you're excited about your new venture and glued to your computer late into the night.

None of these things are necessarily wrong, but it's important not to slip to either end of the spectrum. You shouldn't work so much that you don't have time for lunch with a friend or an afternoon nap, but you should also be careful with a free-for-all schedule that lacks structure. A routine has many benefits. I've tried different schedules, and here's the general overview of what works for me:

Wake up early because my brain is more alert in the morning, and that's when my body naturally wakes me up. Stop the hard-hitting creative work first. This is what requires more focus and thought. Eat regularly and use that time as a screen break. Add in a quick yoga session or a walk in the fresh air – both if I can manage. Work the rest of the day in “pockets”. I will explain it in more detail below. Set a time limit, after which I don't check emails or respond to notifications. Adjust as needed.

I swing more A-types than B-types, so creating structure has never been my biggest challenge. I find it hard to let go, to be flexible, to go with the flow. My work day was once as soon as you can until your time is up . During this time, I've learned that I really enjoy early mornings. My body naturally wakes me up around 6am. I also learned that around 3pm. that's when my brain is completely finished. But if I work from 6 a.m. to 3 p.m. straight, I get eyestrain headaches and I'm irritable. Not to mention that I missed some of the best parts of the day.

All of this to say:structure is important, but don't structure your work life at home so much that you forget to listen to your body and adjust accordingly. I now plan my day in the pockets of time that work best for me. This includes a nap after lunch, so I don't get sleepy the rest of the afternoon. It also includes working in short productive periods with meaningful and useful breaks in between. My way of doing it may seem ridiculous to you, and that's fine. Start building your structure, but don't forget to check in and adjust as needed.

3. When tracking your finances, remember to live.

I love setting goals. I love creating a big spreadsheet at the start of the year to track my goals. One of my big goals right now is to pay off my student loan debt within three years. I traced everything and it's aggressive. This goal comes with savings and retirement account goals. Adding that to my monthly bills and self-employment taxes means a lot of my cash flow is talked about before it even hits my account. I like managing money this way because it makes me feel more in control of my future. But it can become too much. At one point, I tracked all daily expenses to identify where I spend the most. This left no room for a beautiful and unpredictable life.

My financial tactics come from a mix of personal financial coaches that I have read and written about. That's good advice. But I forgot a crucial element:do not forget to live. Track your spending, yes, but be sure to leave yourself some fun money — the funds that don't need to be streamlined or judged. It could be as little as $20 per month depending on your financial situation. Ultimately, you make room for unstructured, benign, and straightforward pleasure.

4. Understand that money always has a cost.

The double edged sword of working for yourself is that there is always another sale to be made. I am a writer, so there are always more ideas to send and more posts to submit. Being the spreadsheet guy that I am, I know how much an hour of my time is worth at this point in my career. In other words, I know how much money I could do if I was working rather than taking a nap or playing beach volleyball with friends (one of my favorite hobbies).

One of the biggest lessons I've learned is that money always has a price. In 2019, I reached a huge financial goal. It was my best earning year yet. I was living in Hawaii and felt like all my dreams had come true. But I was also at one of my worst mental and emotional turmoil during the summer, my favorite season. I often worked from 4 a.m. to 6 p.m. The deadlines were very important and I often dreamed of my work. Every hobby and fun activity brought feelings of guilt because there was always more to do.

I learned the hard way that each new client and each new gig means more money, but they also have costs:the cost of my free time; the cost to my mental and emotional health; and the cost to my physical health at times. For me, reaching that financial goal wasn't worth all the side effects. In 2020, I set myself a new goal:do enough to be comfortable, then take the time to do anything, or nothing. I had to make some adjustments to my spending habits, but I traveled more, laughed more, and made more meaningful memories – to me, those things are invaluable.

5. Start new hobbies that have no tangible value.

I cannot stress this enough. I have been writing and practicing a form of personal development for almost five years. I believe in goal setting, accountability, structure, restlessness, self-care, productivity hacks… the list goes on. I've also learned that it becomes easy to confuse personal development with some sort of tangible step forward. In other words, every action you take in the 1,440 minutes of the day has to move you toward a goal, otherwise it's pointless. For me, it took some flirting with burnout to realize that becoming the best version of yourself is also about doing things you love, just because you love them.

Take a break from your Jim Rohn collection to read romance novels without feeling guilty. Write a short story without worrying about whether it's good or marketable. In fact, don't let anyone read it so you don't feel outside pressure. Build a birdhouse so you can look out the window and revel in the simple art of mastery without wondering if it could turn into a profitable business.

These hobbies complete us as people. They allow us to stretch creative and competitive muscles while keeping the stakes down to a pretty zero with no pressure. If you fail? Impressive. Try something else. If you're horrible at the hobby but love it? Even better. Go on and learn to laugh at all the feelings of I should be better at this.

Cecilia Meis


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Cecilia Meis is the built-in content editor for SUCCESS magazine and Moyens.net. She recently earned a bachelor's degree from the Missouri School of Journalism. Originally from Kansas City, Cecilia loves sand volleyball, new stationery and a big plate of burnt bits.





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