25 Lessons Learned in 25 Years

A funny thing happens when you’ve been in business for yourself as long as I have. You start to get all reflective.

February 2023 marked my 25-year business anniversary.

In 1998, I lost my Copywriter / Producer job at a small ad agency. As I looked for another job, I kept running into two obstacles:

• Agencies wanted to hire those with 5-10 years’ experience (Yet, how are you supposed to get that experience if they won’t give it to you??), and
• Middle-aged male creative directors didn’t want to hire young female creatives because (and I quote one of them), “Why should we hire and train you when all you’re going to do is run off, get married, and have babies?”

Yep, I was livid, too.

Long story short, after looking for quite some time and not finding a good fit, I threw my arms up in the air, said, “Screw it!” and decided to do my own thing. I sat down, set goals, wrote business and marketing plans, and off I went!

Looking back, I have no regrets.

While I started freelancing as a copywriter , I soon started collecting other hats.

In 2003, I founded The Freelance Exchange of Kansas City and have sat at the helm of the organization in some sort of leadership capacity ever since.

Because of this, I began getting requests for media interviews and speaking engagements on a regular basis.

Eventually, I got smart about the speaking part and started charging for it, adding that to the Julie Cortés brand.

Fast forward and, in 2017, I created a much-needed, college-level course, Freelancing 101, for the KC Art Institute , where I’ve taught as an adjunct professor ever since.

Soon after, I opened a coaching arm to my business to offer similar lessons, motivation, accountability and support to my fellow creative freelancers.

All that to say, I’ve definitely learned a thing or two along the way. And without further ado, I present to you:

25 Lessons Learned in 25 Years

1. Freelancing IS a Business—I’ve never quite understood the negative connotation surrounding the term “freelance.” Do you sell a product or service in exchange for money? Do you pay taxes for sales of said product or service? Then, IMHO (Don’t @ me!), you run a business. No matter what the naysayers say, your role, your job, your contributions to your industry make you a business owner. So, own that sh!t.
2. Treat Your Business Like a Business, Not Like a Hobby—There’s a big difference here. A hobbyist does their craft for fun; a business owner does it for profit. If you’re a business owner, you need to shift your mindset and productivity into doing the things you need to do to get ahead, such as: getting educated, investing in yourself, showing up every day, adhering to best business practices, industry standards, legal issues, and more.
3. Act Like a Business, Get Treated Like a Business—When you’ve got your ducks in a row with things such as paperwork, policies and procedures, it lends itself to you getting treated as the freelance professional you are. It’s how you command respect. Discuss the hard things up front. Get everything in writing. And maintain proper business etiquette throughout. Bonus? Things will run much more smoothly in the long run.?
4. Price by the Project, Not by the Hour—Charging hourly is something many freelancers do when starting out. I get it; I did it, too. It’s easier. Yet, over time, you’ll come to realize that clients ought to be paying for not only your time, yet also your experience, your talent, your efforts … and the results you may achieve for them. Your work has value! And you deserve to be paid as such. Project pricing helps you do just that.
5. Get Paid What You’re Worth—Some prospective clients will judge you ONLY on price, often comparing you (with XX years’ experience, awards, etc.) to someone fresh out of school. They’ll wonder why they ought to pay your prices when they can get “the same thing” for much cheaper. Yet you and I both know it’s not the same thing. Stick to your guns. If they’re shopping on price only, do you really want to work with them?
6. You are Not a Financial-Lending Institution—You get to set your own payment terms. For the life of me, I will never understand why some clients will try to dictate your terms. Like those who say, “We’ll pay you after we get paid by our client.” That’s not how it works. And that’s a lot of risk to take. Payment’s due when you say it’s due. You are not a bank, credit card, loan, etc. Do not allow clients to treat you as such.
7. Freelance Isn’t Free—Some clients will try to not pay their invoices at all. It doesn’t matter if they didn’t end up using your work; that’s on them. Think of it like they went to a doctor and got a diagnosis they didn’t like. They may not like it. They may get a second opinion. Yet, they still pay the bill of the first doctor. It’s the same concept. Be proactive in your paperwork. And take legal action when necessary.
8. Always, Always Use a Contract—Louder for the folks in the back! Contracts don’t have to be scary. In an ideal situation, a contract will protect both you and the client. It’s nothing personal; it’s just business. If a prospective client won’t sign a contract, that may be a huge red flag signaling it’s best to walk (read: run!) away. Ask why. If the answer makes you raise your eyebrows, it may be best to find other clients.
9. Look for Red Flags—There are a ton of red flags out there that might make you want to run for the hills , yet some of the bigger ones include: if the client doesn’t treat you with respect, if they demand your attention 24/7, if they ask you to work on spec or for exposure, if they needed something done yesterday, and if they expect you to drop what you’re doing and move them to the top of your queue without paying extra for it.
10. Trust Your Gut—Some clients can be difficult if not downright crazy. Sad truth: not everyone is kind, honest, and professional. Be proactive and communicative, and pay attention to details. And be sure to get everything in writing. If something feels wrong, it probably is. Listen to your gut and walk away if necessary. Preserve your sanity. There’s plenty of work out there from people who aren’t bad for your mental health.
11. No One’s Going to Save You—As a self-employed individual, you have no boss, coworkers, or anyone who’s got your back. That means you’ve got to deal with everything (the good, the bad, and the ugly) by yourself. Being part of a freelance community can help in these instances where you can bounce ideas and stories off like-minded individuals in similar situations to get their feedback, support, and suggestions.
12. Set Boundaries … and Stick to Them!—Some people will try to take advantage of you simply because you’re self-employed. That’s why it’s essential to set boundaries to help prevent that from happening. Be proactive and share these upfront, whether verbally, in an email, or through a Working with Me document or a What to Expect page on your website. The key is for you to uphold these boundaries if and when the time comes.
13. Mindset is Everything—Get in the right frame of mind if you want to succeed. Being motivated, driven, productive, etc., doesn’t always come naturally for some people. The good news is, there are several productivity hacks you can subscribe to in order to help you become that way … simple things like getting showered and dressed in the morning as you would for any other job, sticking to a routine and work schedule, and more.
14. Work on Your Business AND in Your Business—There are many things to be done (or that can be done) in addition to paid client work. Think bookkeeping, organizing, new biz dev, self-promotion, continuing ed, networking, and more. Schedule the time to do these things, even when you’re busy. And, on the flip side, when you’re not busy, take advantage of that time to get caught up or get ahead in these areas.
15. Use Software and Apps Designed to Make Your Life Easier—Don’t get bogged down with doing things by hand or the old-school way. Take advantage of the myriad of tech tools that are available and designed to help you with things such as bookkeeping, tracking mileage, invoicing, scheduling social media posts, sending out emails, and more. This will save you time and energy so you can better focus on your clients and work.
16. You’ve Got to Spend Money to Make Money —You may be thinking, “How can I afford to spend money on tools, coaching, self-promotion, etc., when I don’t have much to begin with?” I totally get it. Yet, if you do it strategically, these things can actually help you make money in the long run. Budget for the things you want, plan ahead, save, and find a way to pay for the things you want so you can get ahead faster.
17. Outsource What You Can—Free up your time and energy to focus on the things that are really important and that you’re good at. For example, you could hire a virtual assistant to help you with admin tasks or a social media manager to create and schedule all your posts. Not good at bookkeeping or taxes? Hire an accountant. If design or web development isn’t your forte, outsource those tasks to someone for whom it is.
18. Identify Your Why —Why is it you do the things you do? What gives you a strong sense of purpose and well-being? Why are you a graphic designer, illustrator, copywriter, etc.? What got you into this business? What drives you each and every day? Is it your family? A problem you’d like to solve? Once you have this established, use it as motivation to inspire your path, find more fulfillment, and make a more positive impact.
19. Be Clear on Your Target Audience—Many freelancers make the mistake of targeting anybody and everybody, casting a wide net in the hopes of getting a bite. Yet, it’s important to get specific. Who’s most likely to buy your product or service? Dive deep into demographics and psychographics to figure out who your ideal customer is so you can focus your marketing efforts (and not waste time, money, and energy!) in this area.
20. You’ve Got to Be Your Own Cheerleader—That means you’ve got to put yourself out there by promoting yourself. I know, it’s not easy for everyone. (Outsource it if that’s the case!) Yet, it’s one of those necessities in business. How are people going to know who you are and what you offer if you don’t tell them? Promote yourself to get the word out and stay top of mind for if and when they need your product or service.
21. An Online Presence is Essential—In today’s digital world, there are no two ways about it. You’ve GOT to be online … whether that’s through a website, portfolio site, and/or social media. Not doing so can be detrimental to your professional reputation, leaving a prospective client wondering if you’re really serious about your business. Make it easy for them to get to know about your business, contact you, and leave with a great impression.
22. People Like to Work with (and Refer!) Those Whom They Know, Like, and Trust—It’s one of the most basic truths of business. That’s why you’ve got to become that person. You can do this through networking, relationship marketing, volunteering , serving the community, writing thought pieces, using basic etiquette , and even through strategic social media posts and engagement. Stand out, form relationships, and be that go-to person.
23. Diversify Your Income—This is the secret sauce! Because freelancing is prone to a feast or famine income cycle, it’s important to have multiple income streams so you don’t rely on just one. For example, I went from being a copywriter to also a teacher, speaker , and business coach . What else could you do with the skills you have? Creating passive income (like selling digital or physical products online) is another way to diversify.
24. Create a Sales Funnel—This mainstay of the sales process is often overlooked by freelancers, yet it can really help bring in and close more business. You’ve got to take a prospective client on a journey from awareness, interest, decision, and action. This may entail a variety of tactics, yet this strategic framework will no doubt help you convert prospects into paying clients.
25. Design a Life You Love—There’s certainly no one right way to go about your freelancing business. Yet there is something to be said for creating a life … a career … that you love. Find the things that feel good to work on and the people who feel good to work with. You—and only you—are in charge of your career. You have to push yourself if you want to achieve your dreams. So go on, and design a life that you love.

There you have it. My 25 lessons learned in 25 years.

Sound off below: What was your favorite lesson?