Half of the coaching conversations I have evolve into a discussion about making a big career change. People often feel stuck, and once they have the space to really dig into what matters to them they realize that the day-to-day grind has kept them distracted from answering one truly important question:
“Who am I, really?”
Because I work with startups a lot, I tend to attract corporate clients who have a secret dream of starting their own company. But what follows isn’t limited to entrepreneurs, and it doesn’t always mean quitting your job.
Whether you’re thinking of leaving your current role, pursuing your startup dream, or just want something different in life, read on.
Who am I?
When I was deciding to leave my consulting job, I was more than a bit lost. Luckily, I had access to two great coaches. One of them gave me an exercise that was exactly what I needed to help me figure out where to go.
I put it off for months. I wish I hadn’t.
You, though, are smarter than I was. You’re ambitious for what you want, hungry for more clarity. You’re willing to put in a little bit of time to take stock of who you really are. Who knows, it could change your life.
All you need is half an hour and ten blank sheets of paper.
Step 1: Write “Who am I?” at the top of each page
You now have ten pages with the same simple header. Take a deep breath, and start answering that question on each page.
Keep it to a word or two, a few at most. Don’t write down what you think you want others to hear, this exercise is for you. It can help to think back to when you were most energized, most alive, or operating at your best.
The answers can be descriptions, statements, whatever you want.
“Who am I?” Highly motivated.
“Who am I?” Compassionate.
“Who am I?” Problem solver.
“Who am I?” Soccer player.
The important thing here is to give a different answer for each page. Don’t overthink it, just follow your instinct.
When you’re done, you’ll have ten sheets of paper, each with an answer to “Why am I?” written at the top.
Step 2: Write “Why?” five times on each page
Space each “Why?” out on the left-hand side of the page, like test questions. You don’t need to leave any more space on the sheet, these are the last questions you’ll write. Just give yourself enough space to answer each one.
This is the hard part. For those of you familiar with the Five Whys and the Toyota Production System, you’ll recognize this as straightforward root cause analysis. This time, though, we’re looking inward.
Now, one page at a time, answer the five “Why?” questions. Each question builds off the last, and the idea is to go deeper with each answer.
Ask yourself this question with real curiosity about the answer. Reflect on it, lean into it, push yourself.
“Who Am I?” Highly motivated.
“Why?” Because achieving great results is important to me.
“Why?” Because high quality matters to me.
“Why?” Because I always want to do a good job.
“Why?” Because if I do a good job, I feel good.
“Why?” Because it means that what I do is valuable.
See the thread here? There are a million opportunities to be highly motivated. In some sense, it’s just a decision on how to behave. But in this example, being valued or doing something valuable is at the core of what’s really meaningful. It’s what really matters for making big life decisions.
Don’t be afraid if you go in circles a bit. Keep pushing. And don’t worry about getting through all five “why” questions, you might be done in three or four.
When you get a statement that you can’t ask “why?” to again, you’re done. When you reach an “ah-ha” moment and feel it in your body, you’re done. Then move to the next page.
Step 3: Cluster and sort your pages
Once you’ve written out the whys on all ten sheets, spread them out in front of you. This is where you collect your thoughts, literally.
As a first step, just take a flip through the pages and review them. Reflect on what you wrote down and sit with it for a minute. See what themes and stories emerge.
Then, look for common themes across the pages. Maybe you came to the same final “Why?” answer, or at least very similar. Group together sheets that you feel belong with each other. These are your core values.
Finally, take your clusters of sheets or individual sheets and organize them by priority to you. Put the qualities that mean the most to you first. There’s no right or wrong, these are your words.
Before you move on, review and take stock one final time.
Step 4: Draft a “Who I am” statement
You’ve now spent a lot of time reflecting and answering the questions “Who am I?” It’s time to synthesize an answer.
You can get a fresh sheet of paper out for this, or you can draft it in an email or somewhere else on your computer. But find somewhere to collect your thoughts where they won’t be lost tomorrow.
I’d suggest you organize this memo to yourself into sections with three parts:
Make a heading for each core value that came out, e.g. “I want to be recognized for my contributions”
Underneath each core value, write out the answer to three questions
“How much am I living this value now?”
“To have more of this value in my life, what do I need to say ‘yes’ to?”
“To have more of this value in my life, what do I need to say ‘no’ to?”
Congratulations — you now have a really great start at defining who you are. This is self-awareness, and it’s the stuff that conscious choice and fulfilling life are built from.
What’s next
Where you go next is totally up to you. Save this document and revisit it daily. Or tuck it away and never look at it again. It’s your call based on what you need.
I’ve found value in sharing this with my partner. I’ve even asked her to help out with some of my “Who am I?” questions, after I did it on my own.
If you’re a founder or entrepreneur, the next step is likely figuring out how to make your daily grind more in line with your values. If you’re looking to make a career change, the next step is likely to define “What’s out there for me?” and see where the two intersect. And if you’re just trying to live a more resonant life, the next step is likely to decide which of the “what do I say yes / no to” answers you need to address.
In any case, put this exercise in your toolbox for later. You never know when you might need it again, and you never know when somebody else might need it.
Please feel free to share, and if you take something meaningful from this, let me know! Wherever you’re going next, I’m sure it will be amazing. Godspeed and good luck.
Originally published in The Ascent