What I’ve learned after 3 years at a startup — and what I’m planning for the next 3.

My journey from college dropout to Product Manager.

I recently celebrated 3 years at Shipt. It’s been the ride of a lifetime, full of twists and turns and ups and downs. I’ve been challenged and stretched and molded. I’ve had great successes and crushing defeats. I’ve learned more than I ever thought I could, and I’ve failed more than I ever thought I’d be comfortable with — and moreover I’ve come to learn those failures have been more important than the successes.

In early 2016, I made a difficult decision to drop out of college. I had a lot of struggles with deciding what I wanted to study, and I didn’t have the funds, nor the desire to put myself in debt to keep the ball rolling. So I did what any rational, sensible person would do — I dropped out and didn’t tell my parents (sorry, mom and dad…).

I had learned of Shipt from a friend, and decided it was worth a shot. I applied for a role on the Experience Team (think real-time customer support), and hoped for the best.

Three years later and I’ve made some big moves — I taught myself how to code, tested software for a year, and now I am a Product Manager leading Shipt’s Payments Infrastructure and Internal Tools. During that time, Shipt was acquired by Target for $550 Million, Birmingham, the city I grew up in and love, is becoming a big player in tech, and the fears I once had around not finishing college aren’t haunting me. It’s been a wild ride to say the least, and I’ve learned so much.

Kick fear in the teeth

Growing up I was a timid kid. People who know me now often laugh when I tell stories of my childhood, and even my teenage years. I was so afraid!

Fear is the great de-motivator.

We fear we’ll never measure up. We fear we’ll never be as good as so-and-so. We fear that we’ll fail. We fear the unknown.

The funny thing about fear is that it just breeds more fear. Fear comes from a place of self-preservation — we want to keep up the image, the facade. We’ve been formed and molded to believe that we will be eternally defined by our failures, and that the reward is not worth the risk. We’ve built up our brick homes and picket fences, our well manicured lawns, and our filtered photos.

But what if we leaned into our fears? What if the embracing of our fears are what make us uniquely human, and uniquely “us”. What if instead of hiding behind our crafted lives, we were real with ourselves… our full selves, our strengths and our weaknesses?

When I started doing this, and I stopped backing down from the things I was afraid of, it unlocked so much potential within me. I view my weaknesses not as problems, but rather the things that make me, me. Kicking fear in the teeth emboldens us to move forward.

Find your tribe

I think the number one thing I lacked a few years ago was a solid group of people who had my back. Loneliness is rampant. This statistic from the US Department of Human Resources is mind-boggling.

Two in five Americans report that they sometimes or always feel their social relationships are not meaningful, and one in five say they feel lonely or socially isolated.

We shouldn’t be doing this life thing alone. Both my career and my personal life completely changed for the better when I began prioritizing relationships with encouraging, kind, diverse people. And it’s hard work. But it’s rewarding. Every personal victory is made better with friends willing to celebrate, every hardship and suffering is more bearable with people willing to bear your burdens, and the hours I spend at work are worthwhile when I get to build products with intelligent, creative, and kind coworkers.

Stop trying to arrive

We all have a destination we’re striving for. Whether it be applying for that new job, packing for the next trip around the world, starting a family, buying a house — we all want to be the better, made-up, version of ourselves.

But there is far more value and beauty in the process than there is in the outcome. We should be big dreamers with goals and ideas. We were made to be creative explorers, pioneers of life. We’re also fickle people. Tell me, how many new years resolutions have you left sitting in a half-filled notebook? How many big goals and dreams have you traded out for mundane tasks and the same old same old. I think I have about a hundred.

Embrace the awkward. Be comfortable with the journey you’re on. The journey of a thousand miles really does begin with one step.

That doesn’t mean you shouldn’t dream. On the contrary, dream bigger than ever before. But don’t measure yourself against a dream that isn’t really yours. What habits can you put in place today that will have changed your life in 5 years. Do that.

What’s next?

I think what I’m most excited about 3 years from now are the things that will look back and think are ridiculous. That’s the joy of growing! I know that I’ll discover new ways to be a better employee, a more intentional friend, a caring citizen.

Professionally, I’m enjoying the work we’re doing at Shipt. I have the pleasure of working on some really cool technology with some of the brightest minds.

Personally, I plan to read and write more. A lot more. I plan to stretch my abilities and learn some new skills, both for work and for hobbies. I plan to take some really fun trips and eat a lot of good food. I’m excited for the next chapter — one that I’m writing right now.

Product @ Fetch Rewards 💳, previously Product @ Shipt 🚀 (acq. Target, 2017). I write about product, payments, food, drinks, and more.