Since when are we supposed to know what we’re doing?

I thought I’d been invited to dinner to inspire some bright young minds. We sat at a long table at a local restaurant; me, two good friends in the Duke administration and a group of fifteen graduate students selected to take part in a global leadership program. We had a lovely few hours together and when next I saw the woman who had invited me she said the feedback had been great. I was surprised to hear that, above all, they were “so relieved” after talking to me.

Last week I spoke to a new coaching client, an executive of a Fortune 500 firm who is anxiously contemplating a career change. Like the Duke students, he seemed most interested in hearing from me how I was able to, “so strategically,” map out my career. Because he doesn’t have a path forward and he’s really worried about it.

I love what I do. I mean, shout-it-from-the-mountaintops love it, but the assumption that I’ve followed a master plan to get here is nonsense. I’ve been pushing back in these conversations, challenging the idea that one needs a blueprint to be successful. And its really gotten me thinking… when did it become necessary to have a plan? Who is requiring this level of lifelong architecting? It seems boring.

Setting goals is fine, I guess, but when you’re continually striving for what’s next (job, promotion, reward, responsibility) are you satisfied with what you have? I don’t know. Observationally, it seems those focused on the future often mortgage now for later. I used to hear this a lot in banking: “I’ll grind it out here for 10 years, make my number, cash out and do something I like.” I just don’t believe in that kind of deferral.

It’s a bit like a highway. I’m in Durham, NC and Waco, Texas is 1200 miles from here. Some people making that journey would fix on that destination and count mile markers. The faster they drive, the less time lost, the less breaks taken, the earlier the arrival. Maybe the GPS is the career plan; speediest route from A to B, avoid accidents, detour only to save time.

I’m down to drive to Waco. I’m also open to the idea that I might prefer Des Moines. I’m on the same highway, but I scan for points of interest along the way. I don’t get off at every exit, but I read all the signs so I know about alternate routes. And when I see a sign for the ‘World’s Best Milkshake,’ I’m pulling off. Maybe while I eat that milkshake I notice I’m in a sweet town with a great beach and rad people. Maybe I forget about Waco; maybe I’ll stay right there, eating milkshakes and surfing?

Because what if Waco isn’t all its cracked up to be? I worked with a CEO for a couple of years who had built his company from nothing. It was eventually acquired in the kind of deal most founders dream of. When the money was in the bank, I congratulated him on achieving all that he’d wanted. I asked him how it felt – “Empty.” was his response.

My masterplan has always been: read the signs and trust the universe. This is how my 17 year old brain did process of elimination to chose a degree and career:

  • I wanted to be in “business” (what does that even mean?)
  • Ruled out marketing because my dad was on the agency side and complained about his clients
  • Operations / OPM / SCM seemed like “factory stuff”
  • Finance and Economics involved math
  • Everything else involved technology
  • OD / HR was the last major standing so I only looked at schools with those programs
  • I needed a scholarship and it wasn’t going to be academic. I got one for music, so I double majored. I wanted to go to Spain, so I studied abroad and added a minor.
  • Ta da! Path chosen.

A family friend was an HR exec at GartnerGroup and gave me a summer internship. I loved it – cool people, interesting work, and so. much. gossip. I worked hard, I made friends. They taught me about laws, policies, hiring, ERP implementations. The gig paid three times what I made as a camp counselor and I thought – ‘this is the best racket on earth.’ I was sold.

When I looked for a full time job after school, tech / tech adjacent companies were responsive because I’d worked at Gartner. To be clear, I didn’t know a damn thing about Gartner’s business specifically or technology in general and my GPA was barely a 3.0. Here’s how my 21 year old brain parsed the three job offers that internship afforded me:
McKinsey required employees to wear suits and the interviewers seemed tense. No one smiled. KPMG Consulting paid 2K more starting salary than the third offer and I had student loans.

The tech bubble burst in 2001 and, miraculously, I wasn’t laid off with most of my department. I also didn’t have much to do, as I was working in recruiting in a major downturn. A mentor in the office introduced me to a newly hired HR Director for the APAC region. She didn’t yet have a team and let me work for her while I waited to see if I still had a job and she waited for approval to hire. Eventually, I worked on PeopleSoft implementation in Asia, the due diligence to acquire Andersen consulting and became a business partner to C-level execs at the ripe old age of 25. Master plan? No. I just stayed flexible, worked hard, tried to be helpful and took good advice from those who knew better.

Things weren’t looking great after the company went public. A mentor in the office was working with a headhunter and offered to introduce me. They had a role for me at an iBank – I had zero knowledge of financial services. In fact, I had not even walked on Wall St. before my first interview. I was offered a job supporting tech clients internally and it paid 20K more, so I took it and stayed for six years.

The first ten years of my career were spent in those two organizations and, mostly, I wasn’t restless. Maybe I didn’t know enough to want more than what I had. I trusted that the people I looked up to would look out for me and, in those early years, they did. Most of the time I just felt lucky.

At a recent meditation retreat with Sharon Salzburg, we were asked to consider all the people who’s effort or influence or generosity led us to be in that room in that moment. I could write a whole other post on the impact that exercise had on me. When I reflect on what led me to doing this work I love in the way it works for me, its with the same sense of wonder.

If there ever was a Waco, Texas, I don’t remember it. I love the road I’m on, even though I don’t know if its leading anywhere in particular. I’ll keep watch for the World’s Largest Ball of String, side trips to waterfalls and an eye on the gas gauge to be sure I don’t burn out. But a destination? I don’t think so. I’m not saying my way is for everyone. I’m am saying, if you don’t have a Waco, give yourself a break. You might end up somewhere amazing.

Since when are we supposed to know what we’re doing?