Avoiding the Career Plan Trap

When I left Microsoft in 2010 after many years of challenge, excitement, success, and failure, the obvious question I got asked was “why are you leaving?” Of course, some were genuinely interested while others were just looking for some salacious executive suite story. The truth was pretty simple – I’d decided it was time to pursue some other goals in my personal and professional life. As I’ve recounted before, knowing when to move on is an important life skill.

"With all of that said, I’ve come to realize that 'career plans' can be a trap best avoided."

As I look back now, that first question was almost always followed by a slightly more interesting query: “what are you going to do next?” When you choose to leave a good job with a great company, people naturally assume you have a “plan.” I definitely wanted to find a way to have impact beyond the world of selling products and making money, and my time at Microsoft had afforded me a unique opportunity to pursue that plan.

Career planning encompasses a significant percentage of the questions when I speak publicly or meet with someone looking for advice over a cup of coffee (or water in my case). “What do you think of my career plan?” “How should I think about the next phase of my career?” “How do I change my career trajectory?” “Do I need a new career plan?” The list of similar questions goes on – and it doesn’t matter whether I’m talking to an undergraduate student, MBA graduate, someone early in their career, or someone who is at my advanced age – the quest for the perfect plan well executed seems fundamental to our human condition.

I should be clear that I think taking the time to create a roadmap for personal and professional development is extremely important. It forces us to evaluate our strengths and weaknesses, consider our desires and ambitions, and contemplate the costs and benefits of various paths. As I discuss in my book Xbox Revisited, having a clear purpose statement, some guiding principles, and a set of priorities is a necessary step in attacking any type of problem. I have a one page “personal plan” in the right-hand drawer of my desk that does just that.

With all of that said, I’ve come to realize that “career plans” can be a trap best avoided. I’m a huge believer that to paraphrase General (and President) Dwight Eisenhower, “planning is indispensable, but plans are useless.” In my experience, the thought that goes into the specifics of a career plan are usually overcome by the dynamics of our lives, the changes that happen in our career and personal environments, and the opportunities that unexpectedly come across our paths. I see power in this serendipity – the events and circumstances that we encounter in our journey that create forks in the road that we never expected. In that serendipity lies career and personal opportunity.

This is not about “luck” or “accidental outcomes” but is much more about recognizing new opportunities and being willing to pursue them even if they change “the plan.” From my own life, a few quick examples:

-- My college plan was to be a lawyer and US Senator – I went into investment banking and then to business school.

-- I have no technical background at all – I spent 22+ (mostly) successful years at a very technical and product-oriented company.

-- I was never supposed to be the leader of Xbox – my job as Chief Xbox Officer was in many ways an “only person willing and available” decision.

-- I met my wife through a post-it note left on my dorm room phone – we’ve been happily married for 32 years.

The important question, then, is how we develop and utilize a plan without getting trapped into the preconceived notions or pathways that restrict our ability to explore and grow. A few suggestions:

1.    Come Up for Air: We all get very focused on the work at hand, the path in front of us, and the next obvious step. It’s incumbent on us to pause periodically, step away from our current course and speed, and evaluate if we are still headed in a positive direction. Taking off the blinders for a moment allows us to ask if we are learning new things, enjoying the people we work with, and being challenged. A breath of fresh air can do wonders to our career trajectory.

2.    Ask and You Shall Receive: Curiosity and the willingness to explore new areas is key to generating unexpected opportunities. Even if we are “on plan,” it’s important to meet with people in other areas, ask questions about what they do, read about new topics, and generally open our minds to what might be possible. When we ask, serendipity often answers.

3.    Knock and the Door Shall Be Opened: We all have managers, bosses, mentors, and partners who guide us through our careers. Making it clear to them that we are open and interested in branching out sets the table for unexpected paths. We should all hope to generate the question, “Would you be interested in…” because that can open doors to an exceptional future.

4.    Know Thy Self: Career plans are frequently more about what we think is expected of us – or what is the “traditional path” – or how others have been successful. Branching in new directions requires a high degree of self-awareness. Are we willing to take risks? Can we thrive even if we fail? Do we know deep down in our gut what makes us happy? What is right for our family? If we can honestly evaluate our strengths and weaknesses, it provides a great roadmap to pursue opportunities and avoid threats as we branch out from the core plan we’ve established.

5.    Keep the Faith: Shifting our career plan – or at the extreme tearing it up and starting in a completely new direction – requires great faith. We must trust and believe that there is a better path in our future and commit completely to taking that new approach. Faith and belief – whether through a religious conviction or personal confidence – is a force multiplier in our career path. When we are true “believers,” more opportunities arrive, and better outcomes are possible.

All of this may sound like I’m suggesting that we weave our way back and forth across the career map, following every gust of wind we encounter. I also know that the generation called “millennials” has a bit of a reputation (whether deserved or not) for being job hoppers. I’m not advocating for anything like this. I am proposing that it is easy to get stuck in a career plan rut – and a paralysis around the planning itself – rather than establishing a roadmap and being open to changes at key crossroads we hit. When we do commit to something, we must do it with the gusto, energy, and perseverance required to make that particular branch of our career a rousing success.

Rather than building the ideal career plan, we should be in search of the optimal balance between job commitment and openness to new opportunities. Finding that balance requires an intentionality and nimbleness that is not easy but can be incredibly valuable in opening new doors. I had the ten best years of my career as a result of a commitment to start and run the Xbox business – and heck, I don’t even like to play video games. Serendipity indeed.