Giving Advice to My Younger Self

I was about to turn 40 and was having lunch with an old colleague at a cafe downtown. I said to him “I’ve been at the bank for ten years, climbing the corporate ladder, and hoping that the next level would make me happy. Now I realize that climbing higher will never make me happy. What should I do now?”

“I know,” I said. “I feel the same way. Why didn’t anyone tell us this when we were younger?”

I was thinking about this sitting at my desk looking out the window at the Brooklyn Bridge. I got a call from Cathy, an amazing new recruit from UNC Chapel Hill. She was looking for career advice and started asking me questions like, “What was the most important factor in your success?” and “What is the best advice you ever got?” After I answered her questions, I said, “These are really great questions but they’re not the right questions.”

“What do you mean?” she said.

“You’re asking what I’ve done to be successful. You should be thinking about what you want to do.”(1)My two favorite way of figuring out what you want to do with your life are  Seven Stories and the Via Character Strengths. Let’s set up some time in a couple of weeks to talk about that.

I like taking mentoring calls while I’m walking around outside. For our next call, I was walking through downtown Manhattan on the cobblestone streets. “I want to be a product manager, like you,” she told me. “I’m going to get a Masters Degree in Information Science which will help me get my MBA. After that I’ll join a consulting firm and that’ll give me the skills to be a great product manager.”

“Hmm,” I said, thinking that this sounded exhausting. “There’s a lot of stuff here. Let’s take the Masters in Information Science. It feels like you’re collecting things just to collect them. It reminds me of the Japanese concept Tsunduku which means buying lots of books and piling them up but not reading them.”

I heard a pause on the line. “How did you know I have a pile of unread books next to my bed.”

“Because we’re the same person,” I told her. Except of course she’s better and more diligent than me, like any good mentee.

We continued chatting about once a month. Then, about a year later, I heard a got a call from her. I heard some rustling in the background. She was packing up her boxes at work. “Rob,” she said, “my current job isn’t giving me what I wanted, so I decided to move to Deloitte as a consultant. That seems like a good way for me to try out consulting and get those consulting skills. Also, they’ll pay for me to go to business school!”

“That’s amazing!” I told her. Though I felt a bit embarrassed as a mentor. Why hadn’t I thought of this?! I felt like I was in Star Wars when Luke Skywalker starts to surpass Yoda. But I was happy that she was moving her career forward such a rapid rate.

We last talked a couple of months ago. It was during the quarentine so I was walking on the beach looking at the ocean.

“I’m leaving Deloitte.” I was not expecting this. This takes her off the career path we were talking about.

“Why?” I asked. Why would she move so far away from the product management path?

She said, “After working at Deloitte for a year I realized that it’s not what I wanted out of life. What I really love is healthcare and medicine. I’ve had some exposure to healthcare at Deloitte and I really like it. Also, I think there’s something incredible about really healing people, especially with this pandemic going on. So I’m going to take a year off to do the prerequisites and then apply to Med school.”

I thought about this. I’m about 40. If I would do this I’d have to take the pre-requisites, go to med school, and do my residency. This would take 10 years and I’d be 50 before I made any money. So I asked her, “Cathy, how old are you?”

And she said, “25.” And I realized that working with her, we were able to shortcut her career. She didn’t have to get a Masters in Information Science. She didn’t have to get an MBA. She didn’t have to get a job in consulting after consulting. Instead of waiting until she was 40 before she knew she wanted to do something different, we were able to shortcut her career path and get it all done by 25. Now she can build a career she’s passionate about.

And that’s when I realized, the best thing about being a mentor is being able to share my life lessons with a younger version of myself.

Feeback to make this better: The beginning isn’t the exact opposite of the end. It starts with where I am in my career and ends with where I am in mentoring. Maybe change the beginning a bit.


1 My two favorite way of figuring out what you want to do with your life are  Seven Stories and the Via Character Strengths.