Five Things I’ve Learned in Five Years of Freelancing

Freelancing
Written By Kristin Hanson

April 1, 2021. My first day of unemployment.

Stepping away was my call, but that didn’t make the facts of the situation less terrifying. I picked up some freelance jobs while looking for a new full-time position. Freelancing for good was never the plan, but five years later I’m still at it.

Through the end of the pandemic. Through the birth of my second child. Through the political upheaval of the past year-plus. I’ve made it.

I’m usually not the type to toot my own horn but I have to say: I’m proud of myself.

Over the past year, I’ve watched so many friends and former coworkers become casualties of this horrific job market. Some have asked me what it’s like to go out on your own and, more specifically, how to do it successfully.

The truth is, I don’t have a simple answer. Independent contracting is just that—independent. What works for one person may not work for another, even if they’re in the same sector.

That said, here are five things that seem universally helpful, no matter your freelancing circumstances.

1. Talk to as many people as you can.

People like to talk about what they do, and most people want to help. Don’t be afraid to ask for a conversation.

Think about people who do the work you want to do. Ask them: How did you get started? Find clients? Market yourself?

Think about the companies or organizations you’d want to work for and find a contact you may know. Ask them: What are your pain points? How do you find freelancers? What makes a freelancer stand out to you?

Don’t ask for work, ask for information. These conversations may not directly lead to income, but they’ll help get your business started and also let people know that, when they’re in the market for your skills, you’re available.

2. Protect yourself and your time.

Don’t work without contracts. Don’t work without having a clear scope of work that illustrates what you will and won’t do. And get granular, even down to the number of emails or calls you’re willing to field. These things take time, and some clients will assume that, if they’re paying you, they can take up as much time as they wish. Save yourself (and your clients) headaches and set scope boundaries early.

3. Pursue free or low-cost professional development.

I’ve learned so much from newsletters, podcasts, webinars, and even just following thought leaders on LinkedIn. Most of these resources are free, and others come at a reasonable cost. Some—like conferences or certifications—are more expensive.

If you come across something you really want to do, don’t let price stop you. Things like registrations or memberships can be classified as business expenses that you write off on your taxes.

If you’re in the communications, marketing, and/or advancement fields, I highly recommend:

(Note: This is not an exhaustive list, just what I could come up with off the top of my head!)

4. Don’t take it personally when people don’t treat you well.

Yeah … I’m still working on this one. In five years, I’ve had a handful of clients drop me, sometimes respectfully, sometimes less so. Even when you do your best and live up to the letter of your contract, some clients simply won’t be pleased. Getting let go stings, no matter how you slice it.

Let yourself feel that sting, but don’t marinate in self-doubt. After some time passes, look back on that client engagement. You’ll notice the red flags you missed or interactions you could have handled better. Change your approach based on that knowledge and move on.

5. Find friends among fellow freelancers.

Although it’s liberating to be your own boss, freelancing can be lonely work. You don’t have colleagues down the hall to ask questions of or just shoot the proverbial sh*t with. That’s why it’s important to intentionally build your own community. Here are some places to start:

  • Look for local networking groups in your field or affinity (e.g., women entrepreneurs).

  • Check out a local coworking spot and strike up a conversation with who you meet there.

  • Ask that second-degree LinkedIn connection you’ve been following for a Zoom or phone chat.

OK, I really tried to keep this to just 5 things but … I’m gonna throw in a bonus…

6 . Don’t quit.

Freelancing can be feast or famine. I’m usually swinging between having a handful of projects to being so busy I’m working day and night. Five years in, I still haven’t found that happy medium.

But I have learned these two things help keep you going through the doldrums:

  1. Keep reaching out. Talk with former clients and colleagues. Connect with local networking groups. Call your friends and family.

  2. Work on things you never have time for. Update your website. Take an online class. Read that book atop your TBR pile.

But do not quit, because the dry spells end—and you’ll want to be ready when they do.

Dang, that was a lot! If you’ve made it this far, I hope you’ve found something helpful here as you start (or continue) your freelance journey. If you have more questions, please don’t hesitate to reach out. I’d love to chat.

To the clients, confidantes, and cheerleaders who’ve gotten me to this point—thank you so incredibly much for your support. I quite literally wouldn’t be here without it.

Here’s to another half-decade of Kristin Hanson Writes!

Kristin Hanson
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