A journey of imperfect choices

What I work on seems to be ever-changing and often coincides with the changes in my life. So here we are again with something new.

It looks like I’m doing it again.

That’s right—a new project. What I work on seems to be ever-changing and often coincides with the changes in my life. So here we are again with something new.

Chances are we met when I released my first font at Sunday Type Co., or perhaps Design Twitter, maybe in the early days of Dribbble, or through my vlog or podcast (which, as it seems, this newsletter is now a continuation of). Those have always been more than just fun outlets to make and share things with you. Those tools gave a kid in his 20’s the ability to rediscover his passion, change careers, and make a living for his family.

It doesn’t seem like long ago when I first asked someone on Twitter how to design at 2x. Oh, and in those days, we were still designing in Photoshop!

Thirteen years later, I’ve climbed through the ranks of Jr Designer to a manager, director, and Head of Design.

They may only be titles, but they remind me of many milestones that define where I was, not just in my creative journey but in my personal life. As a Jr Designer, I was nervous I’d ruin a project. I felt like somehow I had to make something groundbreaking and prove myself lest someone realize I was a fraud. And at home, that stress knew I needed to maintain a job to afford rent and essential utilities. Forget about vacations and going out; there wasn’t enough money. Later, as a manager and director, I knew I had the talent to design things I was proud of, but this stage came with a new challenge of learning to guide other design teams to do the same. I had to learn on the job and seek advice from other industry friends in similar positions. As it turns out, they also felt like they were screwing things up. It’s funny when you realize that you have the skills to accomplish the things you need, but by the time you get to these mid-level positions, your job is to help others. That’s the problem when we try to do everything under our power and don’t realize that we’re there to support and care for others before ourselves. This brings me to the Head of Design. Without a doubt the most rewarding title I have ever held. Much like at home, you’re here to serve others selflessly. Your job security doesn’t hinge on the success or failure of a design but rather on your ability to respond and support your team, which is often like family. And, of course, there are countless more learning lessons at this stage. Gone are the days of imposter syndrome and stressing over rent as a kid. From here on, there is nothing else to prove; continue learning, growing, and enjoying the life God has blessed me with.

Ben Pedersen just wrote about Imperfect Choices, which prompted me to reflect on the journey that led me to write this for you today.

Options are important, but no amount of freedom can produce perfect satisfaction. Acceptance is an important part of life.

—Ben Pedersen

He says that even if you could customize everything around you, you wouldn’t be satisfied. It caught my attention because he’s right. I can’t tell you how many times I’ve made goals for different areas of my life and thought to myself, as soon as I work on these things over here or as soon as those fall into place, things will finally be moving forward. Nothing ever goes according to plan, and eventually, I end up with a whole other set of circumstances. Better than before, but not quite like I planned. So Ben’s post made me think, would I be any more satisfied than I am if I could customize everything around me?

No.

Everything has trade-offs, and our choices lead to outcomes that may be different than what we could foresee at one point, making us wonder if we made the right ones.

Whether I could have done better in some of my past roles, each one, from Jr Designer to Head of Design, has taught me valuable lessons. So today, I choose to learn to love and appreciate more of what I have rather than focus on what I don’t have. That’s a good source of happiness if I remember staying there.

I wonder what trade-offs I’m making today?

We’ll find out. For now, think of this as a friendly letter between friends. I’ll share insights on personal growth, design, and my spiritual journey as I work on my projects.