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15 Lessons After 15 Years of Freelancing


Today (March 3) is our daughter’s 16th birthday. She was born at the exact time of the total lunar eclipse (6:05 pm) in 2007. Maybe that was an omen because the first year of her life sucked bigly, to be honest.

Three weeks after she was born, she started to cry and she didn’t stop for about five months. Seriously. And when she finally mellowed out, my Mom, who had been battling cancer, took a turn for the worse. She passed away five months later, in January.

Yeah, those first 10 months of our daughter’s life were exceedingly crappy for me. I was emotionally exhausted and needed time to grieve before I could do anything else so I took time and space to get my head together. Finally, I emerged from the fog ready to re-enter the world around the time of our daughter's first birthday.

As I thought about what I wanted and needed professionally, I knew it would look different than before. That meant working from home on my own terms as my own boss. And, as luck would have it, I found that.

Actually, I fell into it and the world of freelancing, helping a food start-up  with its marketing communications. That was 15 years ago, and the first step in building my business.

A lot has changed since my first gig and first clients, but looking back at my journey, I wouldn’t change a single thing. Strike that. I’m sure I’d change many things but after 15 years doing of this, I've learned a lot.

15 lessons after 15 years of freelancing

Truth be told, I've learned much more than 15 lessons, but in staying true to the theme of this article, here are the top 15 lessons I've learned as a freelancer, in no particular order:

1. Self-motivation is key – some days it’s hard to get moving and there’s not really anyone  there to give you the kick the ass you need to move forward. That’s why it’s critical to be self-motivated because if you’re not, you may be more idle than productive.

2. Find your tribe – I admit, it  took me a while to find mine but I am glad I did. Without them, I wouldn’t be where I am today. Of course, my husband and kids are part of my tribe, but so are colleagues, other freelancers, referral partners - people who understand your working world who you can talk to, vent to, rant with, etc.

3. Network in person – I used to LOATHE networking, but now I love it. It took a while to learn how to do it effectively, but it is an absolute lifeblood to my business. I did join a couple of networking groups, but now I mostly meet people through other people or through LinkedIn. We'll meet them for coffee (if local) or over zoom (if not local) and it's great.

4. Network online – I found some great places to network online, too, such as LunchClub. It’s a platform that facilitates 1-2-1 meetings for you so all you have to do is login and show up. There are plenty of other options available, too. The point is, network!

5. Make sure you get paid – I invoice at the end of every month, and if a client is late paying by one day, they get a reminder from me. It sucks to have to chase down payments, but you need to get paid.

6. Get an accountant who specializes in self-employed taxpayers – I learned this the hard way and lost a lot of money when I first went out on my own. I didn’t know I needed to incorporate my business and what I could write off so I found an accountant who specializes in business owners like me. It’s made all the difference in the world.

7. Keep every receipt – you can write off a lot as a freelancer so keep all receipts and develop a system to track your expenses. Every year, I tell myself I’m going to be better about recording my expenses, and every year I scramble come tax time. Don’t be like me; be better organized.

8. Get a coach – Freelancing can be lonely and I found I need someone to provide help in the areas of mindset and marketing. I also need someone to kick me in the ass every now and then and hold me accountable to the things I say I’m going to do.

9. Raise your rates – Prices for things keep climbing. So should your rates.

10. Charge by the project – this is my preferred way of doing business and how I work 90% of the time. I do have a couple of clients who pay by the hour but for the most part, it’s all project based.

11. Build an email list – I wish I started doing this sooner. I was in business for about 12-13 years before I started building my email list and sending out a regular email. And even though I was relatively late to the game, I’m glad I did it. Every freelancer needs to have an email list.

12. Some days you don’t feel it – that’s OK. It took me a while to be OK to throw in the towel on those days where I’m just not feeling it, but now I’m at a point where I tell myself it’s better to log off and do something else than to sit in front of my laptop stressed that I’m not productive.  

13. Find the hours that work best for you – being a freelancer means not having to work between the hours of 9:00 and 5:00, but of course, you can. You can work as much or as little as you want, when you want.

14. Set boundaries with clients – this is critical. If you give an inch, some of them will take a mile.

15. Not every client is a good client – I've been blessed with really great clients for the most part, but I have had a couple that I never should have taken on. It's a difficult lesson to learn but a critical one.

And one to grow on – along the same lines as #15, it's OK to fire a client. If they don't value your time, your terms or your boundaries, they are not worth it. Let them go.

I can honestly say I'm so glad fell into freelancing. I know it's not for everyone, but I truly can't imagine doing anything else.

How about you? If you're a freelancer, what are some of the biggest lessons you've learned? 

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