I’ve always loved business.
I discovered that love while handling the bookkeeping in the classifieds section of a local newspaper in high school. By age 21, I was managing a Bank of America branch, trying to learn as much as I could from the people around me. Once I realized that I wanted to experience something outside of banking, I started looking for new opportunities.
And they came in waves.
I recently turned 40, and I’ve been reflecting on how I got to where I am today in my career.
In the last two decades, I’ve accomplished more than I thought was possible when I was 20. I’ve learned tough lessons, made mistakes, and been blessed with the insight of some great mentors.
Here’s what I wish I could tell my 20-year-old self:
The relationships you develop with peers and managers are the most strategic investment you can make, especially early in your career.
A Bank of America executive named Gail Brown asked 20-year-old me what I wanted to accomplish while working there. I told her I wanted to be senior leadership one day. She asked if I was willing to do what it would take to get there. I, of course, replied, “Absolutely.”
Luckily, she saw something in me and gave me a list of things she wanted me to do. Through the gracious help of those around me (I had to ask a lot of questions and learn a lot of processes to tackle that list), I managed.
To this day, I credit Gail for giving me that opportunity and jumpstarting my career with the bank and beyond.
I’d be remiss to not mention Kent here, as well. Kent Gray is my former business partner who taught me more about business than I ever thought I’d know.
I wouldn’t have had the opportunities and achievements I did if I hadn’t formed relationships with people who took an interest in me and helped me. These relationships go both ways, and I had to do my part. Work hard and show people you have what it takes to succeed.
I’ve moved around a lot in my life. When I was really young, it was with my parents, and the rest was of my own doing as an adult. My journey started in Richmond, Kentucky. Then I moved to Cleveland, then to Venice, Florida, then to Orlando, Chicago, Denver, Sacramento, San Francisco and then back to Chicago—and now I’m in Austin, Texas.
Outside those first two moves with my parents, every relocation meant I was taking a chance and betting on myself—betting that I could take on a new challenge and be successful. Every move and every job worked out, some better than others, in part because I went into them with the right mindset.
Sometimes, the best opportunity isn’t where you’re located right now. Remember that if you’re ever nervous about moving for a job. Not only did moving to all of these places give me opportunities that I may otherwise never have gotten, but I ended up learning more than I would have ever imagined. I learned so many new skills and gained a ton of valuable job experience, but I learned even more about developing relationships, making friends and what it’s like to live and work across the United States. Not only did making these moves help me advance my career, I now have friends all over the world.
It would have been great to know that there’s nothing wrong with being unsure about where you want your career to go in your 20s. At that point in life, most people still don’t know exactly who they are, what they want, or what they don’t want. And that’s OK.
You just have to make sure that you don’t waste time being so wishy-washy about what you want to do that you end up not doing anything. The most important thing is to be actively trying to figure out your goals and a plan to reach them—don’t get stagnant and settle.
We’re always told we need to have work-life balance, but what does that actually mean? I love working and I love my personal life—can’t I have both? The answer is absolutely.
I’m very driven and have always been very work centered, and it took me a long time to understand that only focusing on work was no way to live. And I think I probably would have been a better version of myself had I taken a few more vacations during the more stressful times of my career. Being overly tired and stressed makes it so much more difficult to think clearly, and for me, there’s nothing more frustrating than when I’m off my game at the office.
A healthy personal life balances your career. It gives you valuable time with people outside of work. Disconnecting from work, even for a short period of time, is more important than I realized early in my career. It allows you to recharge so that you can tackle work the way you want to tackle it.
I also realized that work-life balance doesn’t mean a 50/50 split. My work life and personal life are fully entwined, and I get benefits from both. Check out my post on the strategies I use to find balance.
Don’t get me wrong—I love to make money, for myself, for the people on my team, and for my investors. But it’s not my biggest motivation by any means. I’ve certainly taken jobs with lower compensation than I felt was appropriate for the role. I did this because I saw a more valuable opportunity to learn and grow.
But the opposite tradeoff never works. No matter how high the salary, if you don’t like the job, the money will never make up for it. After a few paychecks, you become comfortable with the money and are now left with the job itself. You’re going to have many difficult days if you don’t like the job or your co-workers, or you don’t believe in the mission of the company.
If you take a job for the right reasons, the money and advancement will come.
I make mistakes. I can be difficult. I’m not always my best self.
But I am always honest with myself.
Having this awareness is important for three reasons: You need to forgive yourself for being human and imperfect, you want to avoid bringing others down when you’re feeling off, and you want to always strive for personal improvement.
When you’re open and transparent with yourself and your team, it builds trust and understanding that makes it easier to move past difficult situations. That way, if a conversation with a colleague doesn’t sit right with you, for example, you can approach the other person, apologize, and continue with your day with no hard feelings.
On too many vacations, while friends and family were at the pool having a blast, I’d sneak back to my hotel room to work on my laptop or take conference calls. So now I take two different kinds of vacations: those where I disconnect completely, and those where I still do some work but draw boundaries around it.
Make sure you’re not in semi-disconnect mode on all your vacations. It’s not worth it. Your team will be fine. In fact, they will feel empowered knowing you trust them enough to take your hands off the wheel.
Hard work only really pays off when you take the time to enjoy your success.
There are times during my career when I wish I had stopped for a moment to reflect on and appreciate what I was doing. Maybe I would have enjoyed the ride more. Perhaps I would’ve realized I was being too driven, to the point of overwhelming myself. Had I realized that, I probably could have been a better leader.
When you find yourself in a good spot in your career, but you’re too busy to enjoy it, it’s a waste. Work hard, but find ways to savor the moment.
This one is the most important to me. Life is a roller coaster, and it’s easy to have self-doubt and insecurities that will limit what you think you can accomplish.
There have been many, many times when I had to push through doubts and strive for unrealistic goals. I didn’t always achieve these goals the first time, but I never stopped pushing. Today I have the biggest goals I’ve ever set ahead of me, and I’m more determined than ever to exceed them.