“I was 41 when I went freelance. Kids on the verge of college. Nice house. It made the decision very difficult. I thought about it for years and years and years.”
Jeff Winkle wrote about being a freelancer in his college notebooks. But it took a couple of decades of experience before he was ready to take the leap. Now he’s been freelancing full-time for over 6 years and even inspired his twin brother to return to his first love—painting—after running a landscaping business for 20+ years.
Not only does Jeff freelance as a graphic designer (cravecreativeinc.com), but he also opened up a studio with his brother in their hometown (Ludlow, KY) where they collaborate on gorgeous custom artwork—combining graphic design with fine-art painting. You can read more about that story in this Cincinnati Refined article.
I’ve known Jeff for many years, and we’ve shared many conversations about our careers, life, etc. He agreed to share his story about how he got his start, how he decided to go freelance and how it’s worked out. Enjoy!
What was your career like before freelance?
I majored in graphic design in college, then spent about 19 years in the corporate world, working in small agencies, large agencies, etc. I designed for nonprofits, small local businesses and billion-dollar global brands. I did print work, packaging, in-store—you name it. I worked in places that had zero process and everything was a fire drill. I worked in places that were very buttoned-up and maybe had too much process. So I saw a little bit of everything.
Why did you decide to go freelance?
After a few years at my last company, I just flat-out craved way more flexibility and variety. My boss and the company was great about trying to help me get what I was longing for, but I just needed something more.
During that time, I noticed agencies working more and more with freelancers, so I started getting to know some of them. I asked them lots of questions about what it was like, and I did my own research too.
I wanted my work to be part of my life, but not what my life revolved around. Deep down, I knew freelancing was the next step for me. Even though it took SO many years, eventually I decided to go for it.
There’s a lot of thinking and worrying between the research phase and then taking the leap. What was going through your mind during that time?
Like most people probably are, I was worried about the finances. I had two kids—one in middle school and one in high school—so college expenses were looming. I needed to make a certain amount of money to keep my current lifestyle and support my family. It was scary to not know from month to month where my paycheck would be coming from.
I made positive and negative lists. I talked to my wife over and over. I talked to my freelance friends. I talked to former bosses. One guy that I’d worked for in the past and was a mentor to me gave me a lot of confidence. I called him one night to get his perspective and he said, “You can do this! There is no doubt in my mind you can do this.” And that meant a lot to me. So many people told me that they believed in me and knew I could do it…I had to give it a go so I would have no regrets.
And now you’ve been freelancing for 6 years. How has the reality compared to what you imagined it would be like?
It's exactly what I needed. I have much more freedom and variety than I ever did before. I get to choose my own schedule. I get to choose what to work on. I get to choose my clients. I have more free time (SOMETIMES). And I have more money. For me, it's been all about creating something rewarding and meaningful (which is different for everyone).
It can be kinda scary at times and can be really hard, but it is insanely rewarding to call your own shots and create something you love.
What is a typical day like for you?
I keep to a pretty traditional schedule.
I wake up every morning at 5:30am and get dressed. I make coffee and make the kids’ lunches. I sit on my back patio and drink my coffee and enjoy my beautiful landscaping. It inspires me every day!
I usually start working by 7am. Sometimes if I have a busy day, I get started as soon as I wake up.
I’ll browse Pinterest for about 20 minutes. I’m a very visual person, so I have to get some things in front of my eyes, you know? I need to see other people doing cool things.
I also check Facebook and Instagram and update my social media.
I work until lunch (sometimes I have to keep it real quick or not at all).
I might take a “thinking” break, where I get up and walk around but continue thinking about what I’m working on. I do that a lot if I feel stuck. Just getting some exercise and seeing something besides my computer screen usually gets me over the hump and onto something good.
I try to have most of my work done by dinnertime. That way, I can talk to my wife and kids about what's going on, grab a bite to eat, maybe sit on the patio, have a beer, hang out, whatever.
Usually before bed, I stop by my home office and answer email or tie up loose ends.
Is there anything about freelancing that you don’t like?
The thing I probably dislike the most is all the other work you have to do when you’re a freelancer. I love the design and the creative work, but it’s all the finances and bookkeeping and organizing—the work that I have to do but it’s nonbillable.
Sometimes I also miss being around other people. You make really good friends at your jobs. But my studio with my brother John helps with that a lot.
Do you have any advice for someone who’s considering freelance?
Do as much research as you need to do. Talk to other freelancers. Talk to your coworkers. Talk to your bosses and your former bosses. Talk to your spouse or life partner.
It’s scary as hell at first, but it's really not as scary once you get into it. I’ve never regretted it. And I’ve been able to work with so many cool people and agencies.
I’d also say to make sure you’re always giving 110%. Find ways to offer something that no one else does. And be grateful for the opportunities you get. Use every opportunity, even the shitty projects, to learn something and make yourself better.
Great advice, Jeff! Thank you so much for taking the time to chat and share your story! Keep up with Jeff: