20 Lessons in 20 Years of Freelancing

Happy Anniversary to me🥳. This year I celebrate two decades of being in business for myself. As the cliché goes, where has the time gone? It's been a roller coaster since Day 1, but I don't want to get off. Tech is constantly moving. My clients have changed. Times have been good and bad. But some things have stuck. Here's what I've learned...in a nutshell.

1. Client relationships and a strong network are the most important things you can have.💜 This cannot be understated. Relationships are integral to my business and still make up at least half of my work—whether it's repeat business from one client or recos from colleagues.

2. Communication skills matter.🔛 There's no denying it, people hire people. Yes, the consultant must bring the skill-set, but clients want to be comfortable and understood. If you establish a personal connection, your work relationships will thrive all the more.

3. Obey your lifestyle. 🙌 Some consultants prefer to have one client and go to an office. Others like to manage multiple clients and work remotely. There are many ways to work, but however you set up your freelance life, do what's right for you or you'll unhappy in the long run.

4. Know your market worth. 💸 One decision I made from the get-go was that I would never take roles that were under my market value. Occasionally I make the exception for a non-profit or gigs that are super appealing. Stay in your zone and you'll feel good about yourself and the work. Otherwise walk away, head held high, and continue your search for a gig.

5. Risk… take it or leave it. 😬 It's quite possible you'll go months without work. Or have too much work. Or spend hours on a proposal only to lose the job.The list goes on. While the negatives come with the territory, they don’t outweigh the benefits of self-employment (but always have $ in your bank account as back up!).

6. Put yourself in your client's shoes. 👠 Flip the switch to your client’s needs and concerns. Here are some universal no-no's: Don't talk about how busy you are with other clients. Treat them as a high priority. Don't overcommit. Be honest and forthright. And don't miss deadlines (unless it's a damn good reason).

7. Get it in writing.✍🏼 Sometimes we’re eager to start a job without the formalities. Ensure you have all commitments in writing, even if you know the client. What are the terms? When and how will you get paid? Don't get caught flat-footed. It's happened to me a few times and it ain't pretty.

8. Create a network of trusted vendors. 👥 One of the best ways to fortify your network is to work with vendors you like and trust. For my business, that's graphic designers, editors, and other creatives. You'll have a jump-start on ramping up on jobs, along with a great source of referrals. (This also goes for writers. If I'm busy, I refer them and likewise—coopetition works).

9. Be honest, but understand limits.✋🏼 I've been in situations where a client made a decision and I disagreed. I make my case, but in the end they own the project. You can try to affect change, but it’s never a guarantee. Check your ego at the door or reconsider freelance life.

10. Be creative with marketing. 🗣 Most consultants don’t have the time or money to do marketing. Take advantage of low-cost and free opportunities: In addition to my website and blog, I promote my brand through social media posts, write articles for industry pubs, teaching marketing classes, and speak at events. It takes time but is worth the payoff.

11. Change is good. ↗️ 10 years into my business, I moved to San Francisco and decided to rebrand from a marcom generalist to a full-time writer. I'm happy with this decision and confident that I attract the right kind of work and people doing something that fuels my passion.

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12. Add skills outside your comfort zone. 🧠 Similarly, two years ago I added UX writer to my portfolio of skills. I learned a lot on the job and now appreciate how writing for an app makes me a better writer on other projects. Always look toward the future and what the market needs.

13. Immerse yourself in education. 🤓 Every year I try to go to at least one conference plus as many local industry events as I can squeeze in. These are excellent ways to soak in the latest trends, rethink your own ideas, and yes, meet new colleagues and potential clients (write-off included).

14. Money matters, but so does sanity. 🙅‍♀️ I was six years into my business when I fired my first client—I didn't get paid (surprise!). Since then it's been few and far between jobs gone bad, but no client is worth the difficulty. When you cut bait in these situations, you leave space for a client that's a better fit.

15. Follow your gut but leave room for surprises. 🎉 I've been on projects that seemed perfect at the beginning but then turned sour. Or a situation that I thought was going to be a PITA that turned out to be interesting and fun. Try not to pre-judge and leave room for serendipitous engagements.

16. Take advantage of downtime, even if it hurts. ⏳ One of the simple pleasures working for yourself is going to the grocery store, gym, or doing errands the middle of day. But when you have too much time and not enough work, it's stressful. I've learned to appreciate this time for marketing, home improvements, etc. Before you know it, you'll be too busy to have that luxury.

17. Plan vacations, yes, really. 🏖 Pro tip: If you don't plan a vacation, it won't happen. For years I never took a proper, extended vacation for fear of missing work opportunities or disappointing a client. The attitude change comes with confidence, but also with the need for sanity breaks. When you come back you'll be refreshed and ready to roll.

18. Work with friends...if it works.👯‍♀️ Most consultants deal with this at one time or another. Mixing friends and business has generally been successful for me. The key is agreeing that friendship is more important than the work. Not all friends are meant to be business partners. Conversely, I've made friends with some clients and I'm grateful for that.

19. Get some technical skills. 💻 Over the years I've acquired a decent set of tech skills working on my own. Otherwise plan to pay an arm and a leg for help. Do the research, ask fellow consultants, or better yet be BFF's with a technical type. But try to learn yourself before you automatically shell out the dough.

20. It's never too late. 🤩 If I had a dollar every time a curious person asked about joining the ranks of self-employed...and then doesn't do it. It's like jumping off a diving board for the first time. The anxiety is is crazy-making until you do it and get that adrenaline rush! Remember that sage wisdom: It's not the things we do in life, it's the things we don't do that we regret.