Over the years, I’ve collected some exercises and advice about navigating career next steps. I’m finally packaging it up.
Is it time for something new?
Maybe you know that you need a change, or maybe you just know “this isn’t it” when it comes to your job. Sitting with these two phrases can be a litmus test to see if you’re ready for something different:
You should never be somewhere that makes you feel small. (Listen)
You should never be in a place that doesn’t bet on you. (Read)
If these statements pulled on you a bit and made you question where you are, it’s time to start examining if a change is the right answer.
Do you need a Small or a Big Change?
A “small change” is one that can take place in your current work environment. Small changes can have a big impact, and if you know what you need, you might be able to turn a problem into an opportunity. A “big change” might require you to drastically reimagine what you’re doing and who you are, and might have high switching costs.
To evaluate if you need a small or big career change, ask yourself the following questions:
What do you think needs to change?
Do you have the energy to fix it?
Do you have the power to fix it?
If you don’t know what needs to change, sit with question #1 as long as you can and compare notes with others who might be in similar circumstances.
If you answer No to either #2 or #3, the next thing to do is to make a big change.
If you answer Yes to both #2 and #3, you’re eligible for a small change, but give yourself a timebox (I recommend 3 months). What needs to be true at the end of your timebox in order for you to be happy? Write it down. Set a calendar invite with your criteria, and revisit at the end of your timebox. If your criteria are met, you’ve just made a successful small change! Congrats! If your criteria still aren’t met, then it’s time for a big change.
The nice thing about this exercise is that it forces you to be concrete. Chances are: your leadership team wants to help you; they just might not know how to do it.
Getting Concrete about a Small Change
Ask concretely for what you want; your team or manager can always say no.
Things I’ve seen folks successfully ask for to improve their lives without having to make a big change:
Change of scope or responsibilities - You can change your role entirely, or ask to offload the least enjoyable parts of your job to someone else. It might turn out someone likes that work more, or it creates an opportunity for someone else to take it on.
Change of hours - Many managers want to hold onto talent, even if it’s for fewer hours.
Change of location - Especially with more reliance on video conferencing, location is much more flexible.
Change in title or pay - Your manager may have no idea that you are unsatisfied with your pay or title. Make sure you mention your goals to them.
More support - Sometimes, you just need some more staffing. It could be asking for admin support, asking for more headcount, or asking for more money to hire vendors.
In some cases when I thought “I need a change”, I found that it was me that needed to change. I strongly recommend everyone listen to Leadership and Self Deception. It’s told like a story and is only 4 hours. I haven’t met one person that regretted listening.
If you get to the end of these exercises and you have more confidence that you need a big change, read on.
You need to be healthy before a Big Change
One of the best pieces of advice I’ve ever gotten was that you should be running towards something, not running away. During one particularly bad period of burnout, I realized that even if I found something great, I probably couldn’t identify it. I needed to heal before I could run again. These steps helped:
Get active, eat well and sleep - My wise Chinese grandpa always used to say, “If you don’t have your health, you don’t have anything.” When I’ve reached a point of burnout, I inevitably have neglected my body, too. There’s lots of evidence how lack of sleep can make you depressed, and good food and exercise are mood boosters. If you’re struggling to get enough inertia to move, I’ve found Pokémon Go really helpful in building a walking habit.
Get a therapist - A trained professional can guide you back to a place of empowerment.
Be kind with yourself - It takes time to heal. Don’t judge your progress. Surround yourself with friends and fuzzy things.
Take time away if you can afford it - Many tech companies offer paid leave or sabbaticals. Or sometimes it’s just taking a day or two for “vacation” to do the work of healing. If you can’t take vacation, see if there are folks in your support network that can support you to take some “me” time. They will probably be delighted you asked.
Identify what makes you happy, and cultivate it - These books helped me when trying to get out of a funk:
Before Happiness - A number of the exercises in this book illuminated what was and wasn’t impacting my happiness and allowed me to take control.
The Life Changing Magic of Tidying Up - It helps you declutter your stuff, but also a good philosophy around where you put your energy.
Life Plan Workbook - I’ve done the “Exploring You” section at two major junctures in my career, and found out new things about what makes me happy.
Know that it isn’t you - Experiencing gaslighting, morale injury, microaggressions and stereotype threat are unfortunately commonplace in many industries, but they are never the fault of the victim. Folks from minority backgrounds also don’t get as many sponsors, so a career plateau is more the function of systemic prejudice than lack of individual talent. Feeling burnt out and stuck? It’s not your fault.
Sometimes it can take a few months, maybe a few years to heal. Just make sure that when you start searching for your next gig, you need to advocate for yourself. It takes strength and centeredness to do that.
Search for Person-Problem Fit
Now that you’re healthy, it’s time to start thinking about what’s next. I like the framing of “Person-Problem Fit” that I first encountered in this blogpost rich with exercises. There’s no right way to arrive at this, but it is a lot of work. Below are some resources that I’ve found to be helpful for myself and others over the years (many thanks to those who have shared these with me 🙏):
Figuring out the What
Any combination of these exercises might help you narrow in on what you want to do. The key thing is to give them your full attention, and then marinate on the work you did. The answers will eventually come:
Complete the full Life Plan Workbook - Writing down 100 dreams was hard, but the last 50 was where the magic really happened. Only once I was able to get the superficial goals written down was I able to extract values-driven dreams that helped guide my decisions.
Keep an “Inspiration Log” - Write down all the things that inspire you: a news article, an image, a poem, a song, a conversation with a friend. Then pattern match.
Keep an “Energy Log” - Track day-to-day what gives you energy and what takes it away. Many books have recommended this in various forms: Designing your Life, Genius Habit, and the Person-Problem Fit blogpost.
Ask yourself what you hold inside - Spend a day without your devices and write down the answers to the following questions. Don’t worry if you don’t know all the answers, what’s important is writing down your reactions to the questions and everything that might come to mind. Reread everything you wrote a couple weeks later, and see if anything changes or you have more clarity:
What do you fear? What takes away your energy?
What inspires you? What gives you energy?
Where do you want to be in 2 / 5 / 10 / 20 years?
Take some classes and do some interviews - A class or an interview can be a great way to explore an idea space. Even if you hate it, ask yourself why and use the experience to guide your journey.
Things to avoid: Common advice that I’ve seen lead towards the wrong conclusions.
The “write a book” goal trap - Many people want to have written a book, but not many people want to spend hours a day writing. Don’t focus on the end accomplishment as the goal. Focus on what you’ll enjoy doing for hours and hours every day.
The skills trap - Orienting your next step towards building abstract skills is a red herring. If you find something you’re passionate about, you’ll develop the skills you need to succeed.
The strengths trap - There’s a lot of career advice out there about identifying strengths; it can lead you astray. Even if you’re good at something doesn’t mean you’ll enjoy doing it.
Figuring out the How
Once you know what you want to do, then the next step is figuring out the stepping stones to get there. Here’s some general advice to keep in mind, but make sure you don’t jump to this step too quickly. It might be tempting to start solving, but you’ll only be charting a course in the wrong direction if you’re not solid yet about your next step.
Break your goals into smaller subgoals - Celebrate mini-successes early and often. Ride the momentum to your next win. Conversely, if your goals aren’t broken up small enough, the goal might start to feel unachievable.
Build in accountability and rewards - Find an accountability buddy to share your progress with. Treat yo’ self when you reach a milestone.
Build in a tripwire to reevaluate - From the book Decisive, I’ve fallen in love with the concept of tripwires. A tripwire allows you to run in a direction, but gives you an opportunity to check to make sure things are on track before you run too far in the wrong direction. A tripwire can be a timebox, but can also be something like “my personal savings can’t dip below $X”.
Financially plan for your dreams - Finances can either be an enabler or a goal. Find someone to help you (like a financial advisor) or look for grounded advice. Here’s the best article I’ve found so far about how to build wealth.
Finally: You are awesome. You can do things that no one else can. Once you figure out what you were meant to do, run towards it as fast as you can.