Graphic of 17 Things to Remember Your First Year of Freelancing with coffee cups and computersDo you feel like you struggle to figure out how to reset your life when you go into a new job or work situation? I definitely felt that way during my first year of freelancing.

I had just left working a regular, salaried office job, and I didn’t know how I was going to make it without the set 9-5 schedule.


I got through it, I managed to build a company, and I was making twice my salaried income by year two. Here, I’m going to provide you with the tips and tricks I wish I’d known that would have made my first year even better – and more successful.

Because I didn’t have a lot of clients starting out, and I didn’t know how to get them, at first I struggled to make money. I worked in a specialized area of my industry that didn’t have a lot of job opportunities. So, I was hustling, but not making a lot of headway.

That said, I managed to earn the same amount in my first year freelancing as I had in my last year of office work. By year 2, I had doubled my pay.

It wasn’t all roses and unicorns (is that a saying? I’m going with it), but it was a learning experience. Here are 17 key things I wish I’d known my first year:

1. Cut yourself some slack.

This was difficult! But remember, it’s okay to be stressed and not know what’s next. Don’t be too hard on yourself, even if you’re an overachiever like me.

2. Make time for fun.

I really wanted to spend the whole year working, but I learned in my 2nd year that spending time having fun – with my cats, going out with my wife, or my favorite, taking a midday trip to an amusement park once every six months – all contribute to a happier me! And a happier me is more productive.

3. Spend time outside the home “office.”

When I worked in an office, my “escape” was going home. But when home became my office, where was my escape? I learned that going on short walks was a great way to clear my head and get back to work more focused.

4. Eat well.

My first year, I definitely had poor eating habits, because I was struggling to make ends meet. I felt like if I just sent those 2 more emails, I might get a new client.

But that wasn’t everything, and here’s why: 

My health suffered, because I was skipping meals. I know it can be hard to make money that first year, and I definitely don’t expect anyone to get 5-star restaurant meal delivery, but try to take a break for a snack. It will help your energy, and your emails will be more intelligible (don’t ask how I know this).


In your first year freelancing, it might not be the easiest to do this in a budget-friendly way, so be conscious of what you can afford and plan accordingly.

5. Get enough sleep.

This may seem like basic, 101-level life advice, but it’s really important to get into good habits in your first year freelancing. I used to get 4 hours of sleep and wake up exhausted the next day. Getting a standard, healthy amount of sleep will increase your productivity during your waking hours.

first year freelancing weights and jumprope inbriefwriting

6. Work out.

This is something I didn’t do, and, again, my health suffered. Now that I’m in my 7th year of working from home, I’ve found that working out every day puts me in a better mood and makes me more able to tackle whatever comes my way. I don’t think it’s realistic to expect a daily workout from everyone in their first year, but try to take the time a few times a week for exercise. It will pay off.

7. Self-care.

Practice self-care whenever you can. This can be meditating or listening to your favorite song or reading or seeing a movie, but make time for whatever makes you feel good about being alive. Freelancing in its first year can feel like hell, and you definitely want a bit of heaven to slip in there.

8. Read something else.

If you spend your daily life, like me, reading a lot of work-related text, take the time to read something else. Anything else. It keeps your mind active and more engaged when you tune back in to work. Always be learning is a key motto for me, and it serves me well time and again.

And, here’s what reading also does:

It helps minimize the need to do research later. Most freelancing gigs will require some amount of knowledge of something, and reading a lot is bound to bring up something you’ll use down the line, even if it’s just jumpstarting conversation topics. 

9. Staycation.

I didn’t have the time or money for a vacation, but I did spend a couple weekends at a local hotel. That re-energized me for the rest of the week, and made it feel like I was “vacationing” even though I didn’t have the cash for a lavish trip.

first year of freelancing man on phone inbriefwriting

10. Keep in touch with friends and family.

As an introvert, I don’t have a huge circle of friends, but I do have people I care deeply about. I didn’t check in with them enough, and I regret that to this day. Try to remember to check in with the people who matter most to you.

It doesn’t have to be every day or even every week, but give them a text once in a while.

11. Hobby it up.

Don’t forget your hobbies. Whatever they are – writing, knitting, gaming. Spend time doing these things, because it’s brain fuel, and it keeps you mentally feeling more alive. In my first year freelancing, I went back to martial arts, which I hadn’t been doing in a while – double-up on the hobby and the workout!

12. Learn something new.

I started DuoLingo [Not an affiliate link, just a fun thing!] this year to learn French, and I wish I’d done it sooner. A lot of this advice is “brain activity” stuff, but I swear by it, and I know it’s been the most helpful for me.

I was both my most productive and had my highest paid year when I took more time to focus on self-care, self-love, and self-improvement.

13. Have coffee with people.

Okay, so as introverts, we don’t love the socialization thing. I get that. I kind of hate it. But 1-on-1 coffees with work colleagues actually helped me get more work. And I needed the client base.

So – go have coffees or teas or hot chocolates or whatever. Or Skype with someone. Do whatever it takes to keep some of those personal, face-to-face contacts in your life, and you’ll increase your potential for more work.

first year of freelancing house plant inbriefwriting

14. Get a plant.

This is going to sound a little “out there,” but having something to take care of, whether it’s a plant, or a pet (if you have the time and responsibility) – something that’s not a human family member – is a great way to feel good. And feeling good = more productive = happier clients. I wish I’d done this my first year, because now that I have – I’m so, so much better at my job and happier in general.

15. Volunteer.

I have met some of my best recurring clients through volunteer work. I volunteered at a local community theater. The work was mostly data entry, but I met some great folks, who knew other people who needed my services. I only volunteered for 3 days, but it paid off in spades with clients and potential clients.

I intend to keep volunteering other places, and I highly recommend finding a cause you can lend some support to.

16. Document your time.

I journal sometimes, though these days, I spend most of that time blogging (ha!), but I recommend keeping notes of what works and what doesn’t. It’s a good way to track your time and prioritize in the next years.

17. Hustle.

Okay, so everything else here was really about how to get your brain ready for this last one, which is: hustle, hustle, hustle. Let everyone know you’re looking for work. Put up posts on social media about your job. Read job boards regularly. Send cold emails (respectfully! Don’t bombard them) to places that might need your services.

Find new strategies to get new clients, and use them.

Some major questions I get asked include:

How Do I Know When to Quit?

You don’t. I went back to the office my 2nd year! And it was wrong for me. I lasted a month, and hopped right back to freelancing. That’s how I knew that office life wasn’t for me. But you might have a different journey, and that’s totally cool.

Do I Always Have to Be Hustling?

NO. I really hate the “always be working” mindset. I think it creates burnout, and I try to modify my own daily schedule to make time for things like exercise, reading, and spending time with family. Those are key in my mind to a happy lifestyle, and I don’t think freelancing is viable if you can’t find a way to be happy within that space.

Try not to get burned out, if you can help it. You’re just beginning the freelancing journey. Make time to take care of yourself. It will pay off.

What else did you do your first year of freelancing? I’m sure I missed some stellar advice, as it’s been 7 years since my first year of freelancing. Let me know what else I’m forgetting in the comments!

Graphic of 17 Things to Remember Your First Year of Freelancing with coffee cups and computers