The Art and Science of Pivoting CareersFeatured

Bad jobs and bad bosses are just like bad relationships – it’s all about knowing when to leave and, just like breaking up, the process can often feel confusing and draining. Even if you’re not unhappy with your current situation, the average person will change jobs 12 times in their lifetime, so pivoting with intention is critical in making work simply work for us.

From a job in food delivery to tech sales exec and career coach, over the span of 5 years, I’ve changed careers, continents and industries at least 7 times. It was only in the last transition that I learnt the most meaningful change. I went from “running away” (from bad bosses, toxic workplaces, inequitable pay…you know the usual culprits) to “running toward” the vision and work-life that I wanted for myself. Here’s how:

The first step I took was having a frank conversation with myself where I laid out two ground rules:

  1. Knowing what I wanted and simply going after it wasn’t a thing – we are psychologically incapable of predicting what will make us happy if that source of happiness is unknown. From Brianna Wiest’s 101 Essays that will change the way you think, “Your brain can only perceive what it's known, so when you choose what you want for the future, you're actually just recreating a solution or an ideal of the past".
  2. I am a biased, emotional being and that is okay – as long as I’m aware of my biases so they’re not driving me. My availability bias (the tendency to over-index and orient myself around things that come more readily to mind) has landed me in less-than-ideal situations when I’ve given it the power to. It’s caused me to skip important steps and evaluation criteria in my career pivots and be lured by flashy offers. Had I taken a moment to check-in with my values, I would have thoroughly vetted the companies and avoided a rude awakening further down the line. All this to say – acknowledge your biases, leverage them for how they fuel you into action but don’t let them drive you.

It was in establishing these ground rules that I started my year of obsessively researching how could someone – with all their biases and flaws – navigate career transitions effectively amidst toxic work situations and glitzy new offers. As a coach, I began testing these exercises out with my clients. This is a small selection of our best starting points:

  • Get clear on you
  • Understand your context
  • Make the subjective more objective
  • Envision the path forward
  • Consider an internal pivot
  • Explore new opportunities
  • Assess your pivot using a weighted matrix

Get clear on you.

If our brain can only perceive what it has known, then start by taking stock and building a list of values based on your past experiences.

List your past jobs and projects, now brainstorm and write down thoughts that come to you when you ask yourself questions like:

  • On passions: What have you enjoyed? What have you not enjoyed? Why?
  • On work preferences: What gives you energy? What drains you of energy? Why?
  • On skills: What has always come naturally to you? What took time to learn but you eventually mastered? What do you still have a hard time learning to do and/or completing?

You may come up with things like “Solving problems” or “Friendly teams to work with” - compile these thoughts, which we’ll call “Values”, into one list.

If you’re looking for more work values to add, an exhaustive and thorough list can be found here.

Understand your context.

Ask yourself: Where am I in my life? What do I want to change in my current situation? Why?

As you think about your current work situation, brainstorm further and apply Design Thinking principles – almost like a UX Designer coming up with a new product solution. For this, I recommend the AEIOU Exercise to dig deep into the different areas of your current work situation and jot down your thoughts or any additional values that arise from this exercise.

  • Activities - Which work activities are fun/fulfilling and which aren’t? What is my day-to-day role and how do I feel about it?
  • Environment - Where do I feel comfortable/uncomfortable? What is the feeling like in my workplace?
  • Interaction - What interactions with others enrich/deplete me? Who was I dealing with (i.e boss, clients, direct reports)?
  • Objects - What did I enjoy? What defines my work experience?
  • Users - Who do you like to collaborate with/who do you not? Which people will help you get ahead?

Now you should have a list of values and, to make sure you’re not swayed by any of your biases, you’re going to assess just how important each of these things are to you by quantifying them and rating how satisfied you are with them within your current work context.

Make the subjective more objective - put a number on it

First, create a column for ‘Importance Weighting’ and rate each value on a scale of 1-5. Assume a 1 = Not important at all, 3 = somewhat important, and a 5 = extremely crucial to my job satisfaction.

Use this in your job search to hone your focus on evaluation criteria that are important to you so you don’t spend too time and energy on a value that ultimately may not be as critical to you.

Next, create a column for current job satisfaction and again, rate each value on a scale of 1-5 to help you see how your current situation matches up with the values that are important to you. 1=Not satisfied at all, 3=Somewhat Satisfied, 5=Very Satisfied and fulfilled

Envision the path forward

If your list of values is long (20+), refine it by looking at your top rated values and rank your top 10 in order of importance.

Take a moment to reflect when you’re done with this exercise. Ask yourself:

  • What emerged for you when you had to rank these 10 values?
  • How do you feel about the list?
  • What surprised you?

Consider an internal pivot

Do I stay or do I go? Not all career pivots involve moving companies. Sometimes it might mean moving teams or functional roles. Look at how your current job satisfaction scores in comparison to your top 10 values and ask yourself:

  • Where does it fulfill me?
  • Where does it fall short and why? Is this something you can live with or need to address?
  • If it’s something you need to address, can you fix or change it or is this not something that can be changed?

If you’ve decided that perhaps your current job is aligned with you in many ways, but there are things you want to improve, come up with a plan by asking yourself “WH” questions:

What needs to change? Why? Who do I need to help me change it? How am I going to do this? When do I want to see improvements?

Explore new opportunities

Alternatively, if you’ve decided that your current situation is misaligned with your core values and you’re looking to leave but don’t know what you want to do next, use your top 10 values and brainstorm companies, roles, and industries that could be in line with each of them. The internet is your friend.

As you begin to ideate, talk about it. Engage with friends, family or a coach and talk it out. Remember we are biased creatures and have blind spots. Ask them - What other ideas do they have? What do they think of your list? Does it correlate with the person they know you to be? How can they help you find out more about each possibility or begin moving into those new fields?

Assess your pivot with a weighted matrix

By now you’ve either decided on a new path or perhaps an improved version of your original situation. Maybe you even have multiple offers and opportunities you’re deciding between. So how do you make sure you’re trading up and not getting swept up in the moment? As they say, the devils in the details so, go back to your original list and turn it into a weighted matrix.

A weighted decision matrix is a tool used to compare alternatives with respect to multiple criteria of different levels of importance.

To do this, add 3 more columns:

  • 1 column to give you a score of how your current situation is doing (Importance weight x Current satisfaction)
  • 1 column where you rate how well you think this new option could satisfy that value. (If you’re struggling to rate this, ask people in that role/company/team to give you a better idea) Like you did for your current situation, use the same scoring: 1=Not satisfied at all, 3=Somewhat Satisfied, 5=Very Satisfied and fulfilled
  • And finally, add 1 column to give you a score of how your new situation might do in comparison to your current job (Importance weight x New option potential)

When you look at the highlighted columns of your current situation vs the new option, what stands out to you? Does one option seem to fulfill you more than the other? If so, in what ways?

Digging deeper for the value you care about most (those you rated a 4-5 in importance), look at how each job option fares, paying special attention to your top 10 values that you’d previously ranked.

For example – based on the matrix above – if feeling accepted in your workplace is rated as not very important at a 2 versus helping others as the most important at a 5, then assessing how your new offer will enable you to help others in contrast to your current job will be more valuable and impactful to you.

Reflect on what the numbers are saying to you. For many of my clients (and myself), when forced to put numbers and assess work situations across a variety of values, the numbers often uncovered a new part of our stories we weren’t as aware of. Invite conversation with a coach, friends, and family and ask them their thoughts.

At the end of this, you may be tempted to make a decision solely based on the numbers, but I’d caution against that. Go back to the questions and brainstorming you did – people are complex and the numbers are just one of many tools I’ve found to help navigate what can often be messy and confusing transitions.

For anyone looking to apply this, they can download my weighted matrix template here. For those looking to explore more exercises that help build clarity and make their workplaces work for them, they can reach out to me to pre-order their own workbooks with guided exercises and prompts (launching soon!).

Wow this is incredibly thorough and thoughtful. A great read, thanks for posting!
Just what I needed!
This is such a great article. Thank you so much!
This is amazing!! This is perhaps one of the best articles I have come across on pivoting careers. Thank you for sharing.
Bookmarking this for later. Thank you!