How long does it take to truly transition careers? And what is the best strategy for doing so?
These are two of the questions I’m most commonly asked about career transitions. My coaching clients are keen to leave jobs that no longer inspire them and step into their dream job almost instantaneously. What they’re often not prepared for is the transition period – typically at least a few years – where they test their hypothesized answers to the question “what should I do with my life?” and learn as they go.
Cross the river by feeling the stones. – Chinese proverb
I love this Chinese proverb for how elegantly it describes this transition period between careers. The bigger the shift we want to make, the more we need to prepare ourselves for a period of uncertainty that we must “feel our way through” in order to fully step into the next chapter of our lives.
Over the years, after seeing many people navigate career transitions, I’ve started to talk about this period of our lives using the metaphor of bowling. And when it comes to strategies and timing, the two archetypes I typically see are The Strike Planner and The Bumper Bowler.
The (Bowling) Strike Planner
The Strike Planner (thinks they) knows what they want to do next. For example: One person I know, motivated by a personal health scare, decided he wanted to move from a tech implementation role to a strategic role working with rare diseases (without going down the route of becoming a scientist). Another, after having spent years building successful teams in his large organization, decided he wanted to work with other leaders on creating psychological safety on their teams.
Strike Planners try to map out the trajectory of their bowl, calculating exactly how the ball needs to roll to knock down all the pins. Even if they don’t bowl a strike, they are pretty sure they can bowl a spare – or at least get high points on the board – strategically knocking pins down in sequence. As career consultant Richard Rosser, founder of OnUpBeyond, always counsels, career transitions inevitably comprise several moves, as employers will only take a risk on an applicant in one dimension – for example, similar job title, but in a new industry; new role, same industry (ideally same company); same role, smaller (or larger) company. Sometimes we may also need to take time out (or on the side) for education or re-training.
In all cases, sure of their destination, Strike Planners try to plan their bowls in advance to collect the right experience that gets you from A to B. And, in rare cases, someone will bowl a 300 (a perfect game). But for most people, it’s not so simple.
The Bumper Bowler
I actually think even Strike Planners are actually Bumper Bowlers. Because actually, even if we have a sense of what we want to do next in our lives, research on affective forecasting by psychologists Timothy Wilson and Daniel Gilbert has consistently shown that we don’t KNOW what will make us happy in ten years’ time. So, while it’s good to have a goal, we should also be prepared to course-correct along the way.
At the risk of mixing metaphors, think of it like exploring new lands. Back before GPS and Google Maps, explorers had nothing more than the vista in front of them, and perhaps reports of those who had gone before them. With each step they took, new parts of the landscape revealed itself. The mountain pass that looks promising turns out to be impassable. The river that looked so turbulent actually turned out to be the smoothest way through rocky terrain.
The point is: the only way we can reach our destination is by walking the path – and the smoothest path may take us somewhere unexpected. A year into their transitions, the person who wanted to work with rare diseases has found more satisfaction (at the moment) coaching others in similar crisis points; the aspiring psychological safety expert is (for now) a personal finance coach. They got there by following their personal energy and interests rather than by trying to over-engineer their transition.
I have started to describe this experience like bumper bowling. You know how, when you go bowling, you have the option to put up bumpers in the gutters so that your ball stays roughly on track? That’s what career transitions can feel like.
We launch the ball down a new path. Because we’re still learning, our ball is a little wobbly. We hit a bumper (roadblock) – a sign that perhaps we’re not on the right path – that can feel jarring and unsettling. It sets us down a new path, until we hit the bumper on the other side, course correcting our trajectory again. This keeps happening over at least a few years, but the ball eventually makes it down the lane (it doesn’t go backwards!).
You have two options for how to respond when your ball inevitably hits a bumper:
- You can become frustrated with these “barriers” (or your own failure to predict the failed trajectory of this path you set off on); OR
- You can be grateful for these gentle invitations for reflection and course-correction.
Love Your Bumpers
Trying to bowl, let alone get a strike, can be scary (especially if – like me – you are a terrible bowler). There are all sorts of cognitive biases that conspire to keep us in place: status quo bias, the endowment effect, loss aversion. Only a big enough dream (or a big enough upset) can give us the fuel to overcome the inertia we face.
But while the lane you are bowling is your own, the good news is that you are not the first person to have attempted such a feat. Here is some wisdom from other people who have gone before you (and knocked down the pins – although it may have taken more bowls than expected!)
- Give yourself time. Most career transitions take at least 2-3 years, if not longer, from initially contemplating a change to fully “arriving” in the next chapter.
- Expect discomfort. Truly changing careers – rather than just moving to a similar job in a different company – is an act of transformation. Making space for something new means clearing out what no longer serves you, and trying something new. You will, in some ways, be a beginner again (this is especially uncomfortable for people who like to be in control). Give yourself permission to learn. After all, a learning / growth mindset is how you got to where you are today. You can do it again.
- Create your own definition of success. As you step into the unknown, you may start comparing yourself to others as a way of measuring success. I am guilty of this – especially comparing myself to people in my field who are around my age and seem to have achieved so much more. Throw out these external ‘markers’ of success and define for yourself what it means.
- Follow the energy, and be prepared to pivot. As mentioned above, our minds are terrible predictors of what will make us happy. Treat the destination you’ve come up with as a hypothesis to test, rather than a destination you MUST reach. If what you’re doing feels like a struggle, and not in the good way, be prepared to pivot towards something that gives you more energy. You will know for yourself where you want to lean in to hard work vs. when it’s time to re-evaluate your path based on how motivated you feel, internally.
Remember: even the pros don’t bowl perfect games every time. What matters is that you accept the bumps as a natural part of the process.
