My Big Career Bets - 2021 Edition
3 min read

My Big Career Bets - 2021 Edition

An initial look at the three big career bets I'm making for 2021.

A friend of mine, Billy Bob Brigmon, recently walked me through an exercise to help focus some of the various thoughts, ambitions, and curiosities floating around my head. The core concept starts with a deceptively simple question: What are the big bets you'd be willing to take in your career for the next several years?

I've never thought about things from this perspective. On a side note, exposure to new perspectives has been the best part about getting more active on social media and starting to blog. If I hadn't started sharing thoughts, I never would've been exposed to his!

Anyway, his approach is really thought-provoking. I'm not going to use his exact phrasing (since I didn't take great notes in our call), but it goes a little something like this:

  • What are a few "big career bets" based on how you see the world now?
  • For each of those, what evidence exists in the world that causes you to be willing to make those bets?
  • For each of the bets, what are some of the shifts, changes, or disruptions that may happen if this bet is true?
  • For each bet, can you come up with "future case studies" demonstrating the impact? This is essentially just writing a story that hasn't happened yet. Let your creativity run wild.
  • The final aspect of this...for each bet, how do you fit there? What solutions, tools, services, thought leadership, etc. do you provide to leverage you foresight into this bet?

When I originally sat down to think about my career bets, I was a bit surprised at the thoughts that were coming out of my pen. Some of these ideas weren't related in any way whatsoever. Others looked like siblings. Some thoughts felt like good bets, but not necessarily good bets for ME to take.

This exercise forced a new perspective to cross my mind, one that asks, "What change in the world do I want to be a part of driving?"

The world is changing fast, and I'd like to think most of us have opinions, ideas, and contributions we can make to the change to keep moving the world in a better direction. If you were to look at your "career bets" from that angle, what would you want to go do?

Here are the top three bets I'm making, in no particular order:

  • What's the Bet? Leadership teams that adopt lean experimentation and a strong facilitation mindset will outpace the rest of the market. How do I fit? These skills need to be adapted and taught. My experience of lean facilitation and history of working with go-to-market leadership teams positions me to design solutions that fit this audience.
  • What's the Bet? The rise of no-code technology will make it easier for solo founders to build stuff, but the ones who know how to build the RIGHT stuff will be the next class of quiet millionaires. How do I fit? The lean startup methodologies, user centered design, and ruthless prioritization that startup teams have leveraged need to be adapted and taught for solo founders using a no-code loop. My experience teaching at startup accelerators and working with no-code tools positions me to design solutions for these individuals.
  • What's the Bet? The Customer Success mindset and operations will start to "shift left" in organizations instead of being viewed as a post-sales "role." How do I fit? My combination of product management, go-to-market leadership, and customer success experience positions me to help design a success evolution for companies that want to win the experience battle.

I had a list of 7 things that came to mind, but these three things rose above the rest. For each of the 7 bets I listed, I asked myself the question, "Hey, you have to wake up tomorrow and be thinking about X...are you excited about that?" For 2 of them, the answer was a resounding no. For another 2, the answer was yes, but they felt similar enough to one of the above 3 that I combined them.

What's next? Well, I need to sit down and do a deeper thought exercise to fill out the rest of Billy Bob's methodology. Thinking through the evidence, impacts, future stories, and solutions I can provide feels like a good use of time. On a daily basis, though, I'm going to be thinking about how I can tie the content I share back to one of these three themes. We'll see what resonates with the people I engage with, we'll see what really feels like me, and we'll double down on that.

I'm 87% confident Billy Bob will be releasing a small course to walk people through how to do this exercise for themselves. When that releases, I will share it, and I will go through it myself. The clarity of mind after only 30 minutes of this perspective has really astonished me. You should do it, too!

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