The Mentor Sessions


February 26, 2019

Screenshot from Louise Fili’s Skillshare Class: Lettering for Brands

“We’re here for a reason. I believe a bit of the reason is to throw little torches out to lead people through the dark.”

— Whoopi Goldberg

Flashback five years ago, and I was gearing up to start my full-time freelance adventure. I had about a month left in my temporary design job and I knew in just four weeks’ time I would be my own boss. I was equal parts excited and nervous, but with just enough self-confidence and naïveté to believe it would really work.

Had I known then how difficult of a year I was about to have, I wouldn’t have been wasting hours brainstorming about all the amazing projects I thought I was about to begin. I would have been signing up for therapy.

I often receive messages from young designers who are just starting out. Each one wants to know how I got to where I am – doing something I love and making a sustainable living from it. The truth is that the path has been rocky.

Here are seven lessons I learned the hard way during my first year as a creative entrepreneur.

The numbers actually do matter.

I wasn’t concerned with financial planning when I first started freelancing. And I really should have been. I quit my job with a dream to work for myself, but not a lot of experience working with money and no savings account as a buffer. To say that first year was tight would be a massive understatement. I was working my tail off, but just struggling to get by.

It’s tempting when you’re starting out to think you have to prove your worth by doing really cheap work or trading your services for friends and family. But you also need to be responsible and pay your bills. When you look at the numbers and realize that you do need to turn some kind of profit in order to run your business long-term, those trades don’t seem like essential building blocks – they look a lot more like time wasters.

Pro-tip: If you know you’re not good with money, ask for help before starting your venture. Get someone to go through your expenses, the cost of running your business, and what you’ll need for taxes.

Hours behind a desk don’t equal success.

I bought into the mentality that if I worked hard enough, or long enough, that my business would be successful. I actually would wake up at 4:30 a.m. to begin my day and often not go to bed until late into the night. I thought I was in startup mode doing whatever it took to get myself off the ground.

But I really was just exhausted and operating from a place of fear. I’d fill my day with little tasks and crash at night without ever feeling like I moved the needle. Not only was this not productive, it was disheartening and emotionally draining.

Pro-tip: Pace yourself. Work hard, but don’t hustle. Map out your projects and give yourself milestones. Once you’ve finished your tasks for the day – go outside. Call a friend. Make a nice dinner. Read a book. Just don’t keep mindlessly working.

Your social life is crucial.

This was one of my biggest lessons. In that first year, I ignored every friend while I tried to build my business. I withdrew into my head and spent my days behind the screen because I didn’t want anyone to know I was struggling. I wanted to show up as a success, not a work-in-progress.

So it shouldn’t have been a surprise when my relationship broke up, my friends disappeared, and I felt disconnected from the outside world. If I could, I would tell myself then that those friendships mattered, and that I needed to lean into my community during that difficult time instead of pushing away from them.

Pro-tip: Be a work-in-progress. Schedule time to call friends and show up for their important life events, too. Let them in to your journey and share your experience as you learn how to work for yourself.

Don’t be afraid to take on a side hustle from your freelance life.

I remember getting to a point when I was so desperate for creative community and encouragement that I reached out to some people I had worked with in the past to ask if they had any advice. They suggested that I reach out to a local coffee roaster since I had always loved working in coffee during college.

I was nervous about the idea of becoming a barista, because in my head it felt like going backwards from my agency job. I was worried that I would be judged by my friends back home who didn’t understand how important my new business was to me. If I’m honest, I was also afraid of being judged by my new friends in Dallas who had amazing corporate jobs.

But I listened to their advice and it ended up being one of the most rewarding experiences that led me down a path of joy, fulfillment, and growth. I met my first business coach, my current boyfriend, and enough new clients to allow me to truly become a full-time freelancer in less than a year from when I began.

Pro-tip: I learned from that experience that opportunity doesn’t always look like a step up. But when you lean in, you’ll see the hidden potential in new friendships and showing up in your community. You already have everything you need.

Discover your values.

I think the turning point in my freelance journey was when I started working with a coach who challenged me to identify my core values and get really honest about what mattered most. I don’t know why I hadn’t gone through that thought process earlier. I may have been too charmed by the idea of freelancing that I didn’t check in with myself to discover my why.

Knowing my purpose and intentions behind starting my business really helped me to shift my perspective and start to take my work seriously. It was also the moment that I committed to being a brand designer (not a do-whatever-you-need graphic designer, illustrator, artist, glorified creative assistant, etc.) Having a clear sense of purpose and structure in my business helped me to articulate my worth to new clients. In fact, I quadrupled my prices overnight and then booked out for the next six months.

Pro-tip: Find someone who will guide you through the hard questions and help you find your purpose. There are a lot of lies we tell ourself when we’re afraid or anxious, and those lies are keeping us from making a real impact.

You will fail.

Let me talk to you about failure. I’ve experienced A LOT of it since starting my studio. And as a 3, I’m sure you know how difficult each of those situations has been for me… mortifying.

I started a stationery line, no one bought a single piece. I started calligraphy, and quit a month later. I started a course about Squarespace, and regretted it halfway through my first webinar. I partnered with countless other creatives, only to end up with the short end of the stick.

Pro-tip: I’ve gotten really comfortable with failure, but I’ve also become really comfortable bouncing back. Even though I still struggle with disappointment, I am thankful for how it’s forced me to grow as a person.

You CAN do this.

Even as I sit here and remember all of the struggles I experienced, I’m smiling as I remember the wins too. There are few things more profoundly life changing than starting a business. I have grown tremendously as a human, and found an inner strength that has made my entire life better.

And you can too.

Getting the opportunity to fully invest in your dream is a magical experience. I can’t describe the feeling of not only reaching your goals, but having other people come alongside and believe in your vision, too.

A few weeks ago, I decided to start a program called The Mentor Sessions. I know how isolating the first year can be. Hell, I know these first FIVE years have been a roller coaster of change. It was only when I started asking for help and reaching out to mentors that I really turned things around.

Rocky helped me find my values and articulate my aspirations. It was during that time that I discovered my identity and gained a lot of confidence around my purpose. Krysta helped me learn how to be a leader when I started adding people to my team. It was during that season that I became fully aware of my flaws and defense mechanisms, which ultimately led me to my work with the Enneagram.

It takes a village to raise a business, and I would love to be that person that comes alongside and cheers you on while also being honest about what it’s going to take. I owe so much to my own mentors, and am excited and ready to be that person for someone else.

The Mentor Sessions

  1. Sally says:

    Thank you for this raw and uplifting post. I needed this and am so grateful you shared the you’d, the bad and the ugly. 🙌🏻❤️

  2. Christina F says:

    Really incredible messages here – thank you so much for sharing!! I can’t wait until the next one 🙂

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