I recently celebrated my five-year freelance-iversary. This is a pretty remarkable milestone for me and I honestly wouldn’t have thought it’s where I’d end up. I had written this up at the one-year mark and pretty much all of it still applies. There are a few more lessons I’d like to add to it, though.

Celebrate the little things

I am at a point in my career now that I can take more vacation time and not feel as guilty as I would’ve before. The whole reason why I wanted to go off on my own was because I wanted a better work-life balance and not reach burnout so many times. So now I make sure to celebrate as many things as possible: getting invoices done on time, signing a retainer client, my freelance-iversary, and even that I’ve been sending this newsletter consistently for six months.


Say no

While this is something I’ve constantly struggled with, I am getting better and better at saying no. That would be a no to a random person asking me for all the free advice (aka my paid work) and a no to a potential client who isn’t the best fit. I have the privilege to say no, because I’ve built up this business to this point.

I am all about honesty here. If we have a consultation and you’ve told me what you think you want, I’ll let you know if I’m not the best fit for you. My services are pretty niche and it’s possible that someone else can do a better job at what you want than I can.

The other part of saying no is to emotional labor that takes up time that I can be using for my paid work. I am active in my community. I write a lot and sometimes I don’t get paid for it. I will often prioritize my paid work over the emotional labor work, because I need to pay my bills. It’s simple: my paid work fuels the ability for me to do unpaid work.


Listen to what people say you’re good at

Back when I was running a coffee crawl business – because I thought that was the American dream and entrepreneurship was romantic – people would compliment me on various things: writing, photography, and social media marketing. Eventually, I thought, why not combine all the things I’m good at (and want to do) and charge for it all?

After a few years of running other people’s social media accounts, I’ve decided that I’m tired of the day-to-day management and am now more into the strategy and direction part. But I wouldn’t have gotten to this point if I had ignored what people were telling me.


Write / Photograph for one person

One piece of advice I had read somewhere about the trickeries of writing was to picture one person for you to write to. This can be a real person or a fictional one. It’s something that has stuck with me and is how I still write. If I think about hundreds or thousands of people potentially reading my work, I’ll freak out and never get a thing done.

Instead, I picture one person and write for one person. If I can make someone stop and think from a piece I wrote – or a photograph I took – then that’s it. Goal accomplished.


Give back

All those articles about people making millions of dollars on their own are crap. In every scenario, they’re backed by people or privilege, sometimes both. Maybe they had a partner who was shouldering a good chunk of the household chores while they were focused on their startup. Or maybe they had seed money raised from relatives. No one truly “makes it” on their own, there’s always a helping hand around.

For me, it makes sense to help cultivate the local coffee community. I want this industry to keep going and I want new people in it to keep it thriving.


I still don’t regret quitting employment. I have come so far and I’m very excited to see what the next five years are like.