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How to Reinvent Yourself When You’re Lost (2 Exercises)

If you’re wondering how to reinvent yourself when you’re lost, let me share something with you.

I was raised in a very fundamentalist form of Christianity. We had a simple view of the world. We knew who was good and who was bad. We knew what our purpose was and the type of world we wanted to see. ​

When I ultimately left the religion of my youth, it caused a crisis of my identity. I had no frame of reference anymore. The things I believed about myself, the world, and my place in it no longer fit. It was the same experience I went through years later when I left academia after my PhD. I was chasing a professor job that never materialized. ​

We all come to places in our life that feel like this. These are times when the world we thought we knew doesn’t make sense anymore. We need a reset.​

Most people will reach a time in their life and career when they feel lost… stuck. When it doesn’t make sense. And when the world might have crumbled.

In the Catholic tradition, the Dark Night of the Soul is a time when a spiritual seeker feels lost– based on a poem by St. John of the Cross. Although painful, that time of emptiness is said to serve the higher purpose of purification and, ultimately, producing stronger faith.

In a less spiritual form, the dark times in our lives–whether personal or work-life–can produce the same goodness at the other side. But it’s really hard to get through these type of desert periods. And, unlike the dark night of the soul, not everyone sees these times as a divine gift with a happy ending coming.

But often, from the darkness. From the crash and the burn. There can only be one escape…


I wrote these series of questions when I was at my lowest. They’ve evolved a bit, but have been the framework I used to create my own reinvention, and now have shared with thousands over my email list. I hope they help you.

Take a hard look at where you are right now

5 preliminary questions

Where are you in your life. Right now. As one of my favorite motivational speakers, Les Brown, says, “Look at your life. If you’re not getting what you want, you owe it to yourself to do something different.”

  • Do you still love your work and field, but you just don’t know how to turn it into a career?
  • Did you spend years of your life in a degree or walking down a road you hoped would give you a career, but it didn’t? Do you now have to change direction and start again?
  • Are you waking up from sleepwalking, and realizing you’ve been walking down someone else’s path that doesn’t feel real or right to you? Did you do a degree that your parents, your friends, or your guidance counselor told you would be great for you?
  • Or, have you reached a dead-end, realizing that moving forward is not an option.

Wherever you’re at, it’s time to do some inner work to make sure you’re on the way to where you want to get to.

Take a walk. Get by yourself. Take a hard look at where you are, based on these questions.

Where are you at right now? Ask yourself…

1. Am I where I hoped I’d be right now? Is there anything that doesn’t match my picture of where I thought I’d be?

2. What has been driving me, my own dream or someone else’s? Am I on autopilot?

3. Is there a fear that’s holding me back from living the life I want? What is it?

4. Am I where I am because it’s RIGHT for me, or because it makes sense?

5. Am I chasing someone else’s version of success? What would success ACTUALLY look like for me, on my own terms?

How to reinvent yourself

When was the last time you really felt alive? I hear myself typing this and—my God—I sound like a bad bumper sticker. But I’m in too deep now, so I’m just going to go with it!

I’m a firm believer that the thing you spend your life and time doing in exchange for money should be something you believe is worthwhile. Now, we all gotta pay our dues sometimes. I did some work this morning I didn’t love because it pays the bills.

But the long-term vision for your life and work, and the gift you want to give to this world, needs to be something that makes you come alive.

In the beautiful words of Howard Thurman: “Don’t ask what the world needs. Ask what makes you come alive and go do it. Because what the world needs is people who have come alive.”​

So, before getting down to the nuts and bolts of how to build a career, let’s figure out what makes you come alive. I’m going to give you some questions to answer, some homework.

Answer based on any part of your life or anything you’ve done. This is not specific to jobs you’ve had. If the thing you love to do is building model railroads or playing football, I don’t care.

Answer the following questions:

  1. When was the last time I got so engrossed in something I was doing that I forgot to pee? What was it about that thing that held my attention? (ie. being creative, organizing something, solving a problem, etc.)
  2. What’s the best role (paid or otherwise) I’ve ever had? What did I love about it? (There might be some crossover with #1.)
  3. If my labor helped me to fix one problem in the world, either local or global, what would it be?
  4. If money wasn’t an issue, how would I spend my time?
  5. What’s one negative, toxic thing in the way I’m wired that has brought me to where I’m at right now?
  6. What’s one positive, healthy thing in the way I’m wired that has brought me to where I’m at right now?
  7. If I knew I couldn’t fail and money was no object, what thing would I bring into the world?


Let’s turn those answers into your personal work statements. Fill in each of these with your answer from the corresponding number above.

  1. I have to do work that lets me . . .
  2. I love doing work that is . . .
  3. The purpose of my life RIGHT NOW, lived through the work I do, is to . . .
  4. My ideal way to spend my time is . . .
  5. If I’m not careful, my (answer from 5 above) will drive me.
  6. In my best self, I’m being driven by . . .
  7. One of my Big Hairy Audacious Goals is to . . .

Hopefully you followed along with this. It’s a bit tricky, but I found asking these sorts of questions to be life changing. Tape your answers on a wall somewhere you can see them.

Acknowledge who you are and what you love . . . Sit with it

Can I tell you something? I HATE research. I really do. I love people. So why the HELL does someone who hates research do a PhD and then go work in public policy? Because I was good at it. Because I was too afraid to face the reality of what I actually wanted to do, which was be a writer and speaker (not to mention my first world—the religious one—fell apart. So I jumped into academia). Because I desperately craved that “ooh nice” that people would say when I said I had a government job with a pension. ​

Yup, that’s right. I’ve wasted years of my life on things I hate doing because: 1. It made sense; 2. I was afraid to admit to myself what I wanted to do; and 3. It impressed people. ​

Who are you, really? What do you want to do?​

Be brave enough to say it to yourself. Read the answers to the above questions out loud. There’s a truth in it that needs to be acknowledged. ​

Maybe you’ve gone down the completely wrong path for the last 10 years. The question now is, are you going to keep going down it? ​

Acknowledge who you are and the type of work you love to do (not a job title, just the type of work). And if you still can’t figure it out, sit with it a bit longer. It’s worth finding out. ​

Even without a specific job title in mind, ask yourself the question one more time. ​

“Where do I want to go?”​

Hopefully you’ve got the beginnings of some answers and perhaps even enough of an idea to start moving. ​

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