The 5-Step Proven Process to Help You Plan Your Next Career Move

Stop wondering if there is a better job out there for you. Go and do the work to find your next adventure.

If you wanted to go somewhere, you wouldn’t just hop on the first train that stopped at the station.

You’d research where you want to go and then find the best path there.

So why are you sitting at a job that doesn’t interest you, doesn’t motivated you, and isn’t helping you grow? That’s just like boarding a train to… nowhere.

Don’t wait to make your move

I, like many people, had a tendency to stay in my job beyond the expiration date. I chalked it up to loyalty, but if I’m being honest, I was just lazy and scared. It took major, dramatic events to get me to get my butt into action over the years: serious illness, deep resentment, and insidious depression.

But even though I stayed too long, I still made moves. These moves got me into more engaging roles, helping to launch exciting new technologies, creating new companies, and revamping old, staid ones. It’s how I got the opportunity to become a COO and a CEO. Beyond titles and industries, it allowed me to meet and work with incredibly talented, warm, and driven leaders.

The process was challenging for me because I didn’t have a roadmap laid out for me. I had to create it myself. But it doesn’t have to be for you. Below is my proven 5-step process to finding where you want to head next.

The bad news?

It will take time. For some folks, you’ll be well on your way in a few weeks and for others, it might take months and even a year.

The good news?

This process isn’t hard, and anyone can execute it. You can be a high school dropout or a multi-term executive. It’s the same for everyone.

Get started today and if you want to make it more fun, bring a friend along for the journey.

5-Steps to Your Next Career Move

1. Write your obituary

Photo by The Good Funeral Guide on Unsplash

I first learned of this exercise from “What Color is Your Parachute” by Richard Nelson Bolles. It’s such a simple activity in many ways. And yet it is also an existential question, one that hits you at your core. It challenges you to deeply examine what matters to you and how you think about your legacy.

When I did mine at 22, it revealed to me how little the things I was prioritizing actually mattered to me.

While financial well-being and financial security were important, I wasn’t motivated by large sums of money and the things that money could buy in the ways that others around me were.

I was very happy with my Toyota Corolla and driving it didn’t make me feel less successful than my colleagues driving BMWs or Audi’s. I didn’t need a pair of Jimmy Choo’s or a Chanel handbag. This is what the people around me valued. And that was OK. I wasn’t judging what my friends or colleagues valued. I just didn’t value the same things.

And yet in my day to day, I was easily influenced by their actions. If they were going to Cartier to get a watch, I thought, maybe I should as well. If they were going on a fancy vacation, should I be booking one, too? I wasn’t confident in using my own yardstick.

“There's an African proverb: 'When death finds you, may it find you alive.' Alive means living your own damned life, not the life that your parents wanted, or the life some cultural group or political party wanted, but the life that your own soul wants to live.”
​— Michael Meade

Writing my obituary clarified what mattered to me and what didn’t. It gave me the confidence to carve a career path that met my needs and my standards. And it allowed me to see the opinions and choices of others as information, but not necessarily as guidance. It was up to me to determine if what others were influencing me to do was right for me.

How to get started:

1. Recognize that this is 100% your decision — There is no one way to write your obituary. There isn’t a template you have to follow. There isn’t a specific length or set of elements you have to cover. If you really feel lost, go to the NYTimes or some other publication’s Obituary section or search for some online. Read examples with a lens towards how they make you feel and jot down what resonated with you.

2. Find a quiet place and give yourself enough time — You can meditate, listen to calming music, or go for a walk. This is something that should come from your inner sage wisdom. Don’t force it and give yourself enough time to visualize it and write it down. It’s also OK to write this over several sessions.

3. The words are less important than how they make you feel — This isn’t a writing test. If you only have what feels like random thoughts or disjointed ideas, that’s OK. Write them down. you can edit later.

4. Once you have a draft, use it to assess your current life — The power of the obituary is that it creates your guideposts for your career, your relationships, your priorities, and more. Once you have a draft, use it to help you assess if how you are spending your time and resources matches up with what you truly care about. Here are some sample questions:

   1. Am I pursuing my career in a way that aligns with my legacy?

   2. Are there ways to make my job better align with my values?

   3. When I look back at the end of my life, what will I have wished I’d taken a risk doing in my career?

5. Share it with your trusted circle — When you are ready, use your obituary as a conversation starter with the people you most trust in your life. They will both learn something about you when they read it and they can help you reflect on it and what to do next. Some sample questions to ask them include:

   1. Does my obituary capture me and what matters to me? What did miss or get wrong?

   2. What surprised you about what I wrote?

   3. Given what I wrote, where do you think my current career (or life) is most out of alignment?

2. Know your non-negotiables

Photo by Katie Harp on Unsplash

When you are starting to search for what’s next, it’s helpful to know what your non-negotiables are. These are the bare minimums you need in order to move forward.

Why only list the minimums? Because once you know the minimums, it’s far easier to be creative, take calculated risks, and try something different.

When you have a long list of requirements, which might include nice-to-haves and not just must-haves, it makes it harder to be open-minded and strategic about your exploration process. When the list is too long, nothing will be a fit and you’ll give up before you start.

Most non-negotiable lists comprise some combination of the following categories: money, level (including authority and managerial oversight), title, location (including travel required), industry, function, hours of work, and people. But don’t be married to these and don’t feel like you need to have requirements for any or all of them. Only list what actually matters to you.

How to get started:

1. Write down what comes to mind first — If you think you need to make $150K a year, great. Write that down. If you know that you need remote work to take care of loved ones, write that down. Don’t overthink the list. Remember, it’s not about length. It’s about what is a must. And less is truly more here because less means fewer restrictions on your path forward.

2. Verify your assumptions — Maybe you’ve assumed that your partner expects you to make more money. Or maybe you have managed teams for years and are scared to become an individual contributor even though people management has recently been stressing you out. Check your assumptions before you commit to them. Talk to your partner, talk to people who have switched from managerial to IC jobs, etc. Don’t assume something you haven’t checked.

3. Reflect on the list regularly — The world changes rapidly. So make sure your list is up-to-date. If your partner gets a raise or they lose their job, your requirements change. Sometimes, the shift isn’t that obvious, it’s more gradual. Setting aside time to review your list periodically will help you be strategic when you make your career decisions.

3. Wonder “What if…?”

Photo by Yuheng Ouyang on Unsplash

Once you know what matters to you — existentially (obituary) and practically (non-negotiables), now you can and should dream a little.

One reason I have so few regrets in my life is that I gave myself room to dream throughout my career.

What does room to dream look like?

It means taking the time to wonder, “What would it be like if…?” or “I’d love it if I could one day…”

A few of my dreams that came true because I asked “What if…?”:

• Worked at the forefront of digitizing the media industry with some of the largest media and technology companies

• Launched a $50M e-commerce business with some of the largest luxury brands, surrounded by makeup artists, creative directors, photographers, and models

• Grew a social impact business that delivered more than $250M in skilled labor to the nonprofit sector

None of my dreams were likely to happen. Nothing in my experience before each happened was an indicator that I would get the opportunity to even try to play in the spaces I did.

So what made the difference?

Being curious and unafraid to wonder openly about what was possible. I literally said things like, “I like media. What if one day I could work in media?” Or things like, “Gosh, fashion is so much fun. What if I got work in fashion one day?”

You can do this, too. All you need is the courage to let your imagination wander.

How to get started: