How I transformed my life: a guide to personal reinvention

Spring 2015: For nearly a year, I’ve had this nagging feeling that something important is missing from my life. I run through the mental checklist:

  • Business? Running well.
  • Friends? I see them often enough. Those far away I talk to and email.
  • Love life? I have an amazing girlfriend.
  • Physical health? Check.
  • Mental health? There is something nagging at me…
  • City I live in? Eh, I don’t care for it it.

For the life of me, I can’t figure out what’s wrong. I just know that something is…


Looking back, it’s funny how much I was deluding myself. A more accurate version of the checklist above:

  • Business? My heart’s not in it.
  • Friends? I don’t see them nearly often enough.
  • Love life? The woman I was dating at the time was amazing, but we weren’t right for each other.
  • Physical health? Check.
  • Mental health? I should have been paying wayyyy more attention to that quiet nagging feeling (and you should too…).
  • City I live in? I hate this town.

What strikes me is just how out of alignment I was with myself.

From May 5th 2015 – May 5th, 2016, I went on a mission to realign myself with my truth. Doing this was not easy. Personally, it required ending a serious relationship, selling my stuff and leaving Washington, DC. Professionally, it required walking away from a thriving speaking business that I spent the better part of a decade building.

Before I began this process, I felt like I was just going through the motions. In fact, feeling subdued had become normal for me.

As I started reinventing myself, I began to feel alive again. The process was hard. A lot of the time it felt like a free fall. In any given week, I would feel on top of the world one day and dejected the next.

Today, I feel more like myself than I have in ages. Friends comment that I sound happier and more at ease. Things that I had to work for in the past come easily now.

Is my life perfect? Of course not. But it’s  better than it’s ever been (by far), and this is the direct result of finding the courage to reinvent myself.

What follows is my personal account of reinvention, as well guidelines for those who want to reinvent or recalibrate themselves as well.


Create an inflection point

Reinvention - inflection point

May 5th, 2015, Washington, DC. on the roof of N*’s car, watching the planes land. N* looks at me and asks, “So where are you at with our relationship?”

I’m not ready for this. I know we need to break up, but I want just one more month with her. Or at least another week. She’s amazing. I’m not sure I’ll ever find another woman like her.

I’m almost shaking as I open my mouth. I don’t want this to be real…

I take a deep breath. I tell her I don’t see this working out long term. She tells me she hasn’t been happy either, and suddenly, that’s it…


Let me guess: you’ve been wanting to change your life for a little while now.  You’ve read a few self-help books and told your friends about your bold plans. Maybe you’ve even taken a bit of action.

For some reason though, you’re still spinning your wheels.

Been there.

If you really want to change your life (as opposed to just talking about it), you need an inflection point.

An inflection point is a bright line that makes change inevitable. All you have to do is jump over it.

There are two types of inflection points: the ones you create, and the ones inflicted upon you. Each requires a different approach in order to be effective.

If you’re creating an inflection point, burn your ships:1  There was a lot in my life that needed to be recalibrated: my relationship, my city, and my work.

Changing all of those things at once was so intimidating that it felt impossible. In fact, on May 6th (one day after the breakup), I wrote to my friends, “Most of me feels as though I’ll have to live off the financial and emotional goodwill of my parents or friends or something… I hate that changing my business, my city, and my relationship are all things that I’ll have to do more or less at once. I wish I could do them one at a time, but that’s not really the hand I’ve been dealt.”

After N* and I broke up, I knew I needed to take life by the reigns. I was also afraid to make so many significant changes at once.  To ensure that I actually took action, I informed my landlord that in six weeks, I would be breaking my lease. Without an apartment, I would have to leave Washington, DC, which was something I’d been yearning to do (and putting off) for over a year.

If you need to create an inflection point in your life, here are a few ways to do it (just make sure that you’re leaving something that doesn’t work for you):

  • Ending a long-term relationship
  • Quitting your job
  • Starting a business
  • Embarking on extended travel, especially with a one way ticket
  • Getting professional help for persistent mental or physical health problems
  • Moving from somewhere you don’t like
  • Investing a large sum of money into yourself to help you become the person you want to be (going back to school, doing a personal development retreat, hiring a personal trainer, etc.)

If you’re struggling to create an inflection point, then you’re probably avoiding a lot of pain that you really should be feeling. Feel the pain you’ve been hiding from and let it inspire you to take control of your life.

If you’ve had an inflection point inflicted on you, use the inertia to change your life: Some events are so dramatic, that they will automatically create an inflection point. A few examples:

  • Being broken up with by an intimate partner
  • Getting fired from your job
  • Losing someone you love dearly
  • Surviving a serious injury or a near death experience
  • Coming into a lot of money
  • Losing a lot of money

If you’ve just experienced one of these things and you feel like you need to make sweeping changes to your life, now is the time to do it. Use the energy from the inflection point to fire you forward. Consider asking a friend to hold you accountable and to check in with you for the first month or two as you begin to make changes to your life.


Trim the fat

June 30th, 2015, my last day in Washington, DC: It’s surreal. Everything I own fits easily into a rented Jeep.

I grab a coffee and walk around the neighborhood to say goodbye. Then, I hop in the Jeep. As I drive away, my entire system floods with energy and emotion.

It’s taken more courage than I thought I had, but I’m starting to feel like myself again. It’s been… lets just say it’s been a long time.


One of the most common ways that people lose touch with themselves is by filling their lives to the brim.  

As you reinvent yourself, you need as much space in your life as possible. This means getting rid of the junk that’s not serving you. Be ruthless as you eliminate things from your life. A few areas to look at:

  • Relationships: do you get psyched to spend time with the people in your life? If not, spend much, much less time with them. It’s better to be lonely, than to roll with people who make you feel small or mediocre.
  • Professional organizations: are they actively improving your professional life? If not, leave.
  • Volunteer organizations: are you still enthusiastic about the cause and the organization? If not, resign.
  • Possessions: the things you own, own you. If your house, apartment, or office is cluttered, your life is cluttered. Get rid of the things you haven’t used in the past year (better yet, the past six months).
  • Extracurriculars: rec sports teams, clubs, classes, professional commitments beyond the scope of your contract, etc.  If it’s not making your life better, kill it.
  • Habits: if you have habits that work against your happiness, it’s time to ditch them. Common examples include mindless Internet surfing, watching more than 60 minutes of TV/day, shopping for the sake of shopping, eating unhealthy food.
  • Work: if you hate your job, it’s time to quit. Go on a financial fast and save enough so that you can get by for three months, then quit. Do this even if you don’t have another job lined up. If you’ve been spinning your wheels, there’s a good chance you need to quit before you get a better job. You can always pickup part time work at a coffee shop or drive for a ride share service.

It’s common to wait for perfect circumstances before you start changing your life. Here’s the thing: it doesn’t work that way. You cannot reinvent yourself by waiting around for some fictional deus ex machina to set everything up for you. You must begin by clearing out the shit. When you do this, you’ll create time, energy, and space to for the new you.

Here’s what I had to clear from my life:

  • Washington, DC, where I had lived for six years
  • Most of my possessions
  • Commitments to non-profits I was no longer aligned with
  • Speaking engagements
  • People who brought me down
  • Reddit
  • Conferences and organizations (including a few elite ones I was lucky to get into) that were not worth my time or effort


Start by addressing the real issues

July 2015, Ireland: I can’t stop crying. For the longest time, I’ve been telling myself (and everyone else) that I had a dream childhood.  I claimed that I felt blessed to have been a successful child entertainer. I thought that it laid the foundation of my current success.

Now, for the first time ever, I’ve admitted the truth: I hated being a child entertainer. Not only that, but it fucked me up.

Though I’m sobbing, I’ve never felt so free.


Let me be blunt: if you’re in a situation where you feel the need to make dramatic changes to your life, there is an underlying issue that needs to be addressed. The problem isn’t that you need to change your life; it’s that you have accepted a mediocre life for so long.

Something happened in your past that has tricked you into believing that you aren’t worthy of an amazing life. That same thing is making it hard for you to create the life you deserve. Use this period of recalibration to work with a professional and heal the wounds that are holding you back.

As much as I love self-help, there is nothing that compares to working with a professional. By professional, I mean any of the following, a:

  • Coach
  • Psychologist
  • Psychiatrist
  • Mentor

Personally, I went on a week-long retreat in Ireland led by a coach I trust and admire. Looking back, a good psychologist would have done the trick too.

Emotional wounds do not heal themselves; they grow old and sabotage you along the way.  These wounds need to be healed, and now is the perfect time to deal with them.

You can skip this step, but I hope you don’t. You deserve amazing mental health. By giving yourself the love and attention that you need now, you’ll be setting your future self up for even higher levels of happiness and success.

One thing I can promise: future you will be thrilled that present you gave yourself the care you need. If you don’t, future you will be pissed (and stunted).


You know those things you’ve been dreaming of doing for a few years? Do them.

For years, I dreamt of spending a solid week with my close friends from high school. I wanted to get to know them as the adults they’d become.

Sure, I saw them at Christmas and Thanksgiving, but it never felt like enough. I wanted an entire week. Spending real time with them was something I had wanted to do for years, but never actually got around to.

A huge part of reinventing myself was checking big items I had been dreaming of off the bucket list. For me, that included:

  • Spending time with my high school friends
  • Visiting the summer camp I grew up at while camp was in session
  • Kissing an ex from way back when who I was still attracted to (I don’t actually recommend this, though I’m glad I did it.)
  • Returning to Montreal, where I spent my early 20’s

Most of these things were insanely fun.

They were also deeply healing. Reconnecting with the people and places that shaped me reinforced my sense of self; revisiting my past helped me understand where I came from. Kissing my ex allowed me to let go.

If you’ve been dreaming of doing something for a long time, it’s important that you actually do it, and now is the time.

Practically speaking, it’s good to work it out of your system; it will allow you to tie up loose ends and create a fuller, more complete life.

Psychologically speaking, there’s a reason these things have been lingering on your mind, and it’s time to find out why. In doing so, you’ll learn more about your true self. You may also create emotional openings that will bring you closer to becoming the person you’re meant to be.

To be clear, I’m not saying that you need to revisit your past like I did. What you need to do is take action on all of those things that you’ve wanted to do for a while, but haven’t.


Resist the urge to plan everything out

August 2015, chatting with my family during a visit: “I’m going to spend a few months traveling and looking for a new home.  Though, honestly, I’m pretty sure I’m moving to Durham, NC. A bunch of friends live there, the cost of living is low, and it’s a quick flight to many of the people I love. I’ve also been there a few times and really enjoyed it. Durham is the perfect place for me!”

Only one problem: when I got to Durham, it was clear that it wasn’t the perfect place for me.


As you reinvent yourself, it will be extremely tempting to plan everything out and make decisions as quickly as possible.

Don’t. Doing so will close you during a time in your life when staying open is critical.

Besides, if planning was all you needed to do to solve your problems, you wouldn’t have any. You could just sit reflecting for a few hours in a coffee shop, and you’d be all set. In fact, I bet you’ve already tried that.

Stay open. Wait to make big decisions until you have clarity.

If you’re having trouble getting clarity, start by making small decisions to test the waters. As I was looking for a new place to live, I visited nearly 20 different cities trying to find the one that was right for me. When I found a city I liked, I stayed for a week or two feeling it out.

If you’re having trouble staying open during this period of reinvention, it’s probably because the constant change is wearing you down. I get that. Spend a day or two recharging. I like to hole up and binge watch Parks and Rec. (More on how to handle the emotional chaos of change, here).


Experiment. A lot.

October, 2015, Mexico: I’m clutching my coffee. For the life of me, I can’t remember why C*, S*, and myself decided to host this seminar at 8:00am. I don’t even like being awake before 8:30….

Regardless, the room is filling up, and I’m getting excited. As the seminar unfolds, I notice something amazing happening: every single person we’re working with has had a real breakthrough. In fact, they’re all crying right now because each one of them has gotten in touch with something they’ve been needing to feel or realize.

I feel completely in my element.


The only way to create a better life for yourself is to take action and see what happens. While you’re going through the reinvention process, say “Yes” to as many opportunities that intrigue you possible (just make sure they don’t become long-term commitments).

As you have new experiences, you’ll gain clarity about who you are and how you want to live. Once you find something that clicks, own it.

During my transformation, I knew that I wanted to leave my job as a speaker, but I didn’t know what I wanted to do instead. I dedicated all of October to finding out by seeking new opportunities and accepting invitations that seemed cool.

I learned that I loved giving keynotes with friends (as opposed to solo), that I had a surprising gift for one-on-one work, and that I thoroughly enjoyed running retreats for small groups. Today, these discoveries actively shape my business’ future.


As you complete your reinvention, reflect back on where you came from.

11:00pm, May 6th, 2016 at a coffee shop in Denver, CO: one year ago, I wrote a long email to my close friends. I was heartbroken and afraid of the changes I needed to make. I wanted to feel their love and support.

Today, it is exactly one year later, and I’m sitting down to give them an update

As I do, I go through that mental checklist to examine my current life:

  • Business? I love spending my time writing and doing one-on-one work with people. Not only that, but I’m on track to make more this year than I ever did as a speaker.
  • Friends? Though I’ve only lived in Denver for six months, I have a better, more active social life here than I did in Washington, DC.
  • Love life? I’m single. While it would be nice to be in a great relationship, I don’t feel the need to rush it.
  • Physical health? I’m in the best shape of my life.
  • Mental health? One of my friends mentioned that I’ve become effortlessly happy, confident, and relaxed. While I wouldn’t personally say it’s “effortless,” I am happier than I’ve ever been before.
  • City I live in? Oh hell yes!


Changing your life is turbulent, and the timeline for success is unpredictable. For me, it took about a year to make all the necessary  changes.

When you commit to changing your life so that you may live as authentically as possible, you are bound to succeed.

When success sneaks up on you, pause to take inventory of your new life. You’ll be delighted (and hopefully proud) when you realize just how far you’ve come. You’ll notice that in many instances, you exceeded your own expectations. You’ll notice that you’ve become the best version of yourself yet. That’s an amazing feeling.

Your final task is to celebrate yourself. Share the details of your transformation with your close friends (they’ll be glad you did), and buy yourself a gift. Make it something that you will use or see regularly. Let it act as a reminder of how powerful, capable, and downright awesome you are. Watches, necklaces, tattoos, jackets, or bracelets all work well for this. Personally, I bought a cool hoodie.


Final tips for reinvention

I want to leave you with two pro-tips on how to handle reinventing yourself.

First, prioritize your physical and mental health. For me, this meant a steady regimen of meditation, journaling, and exercise. Find what helps you stay grounded and healthy, and stick with it.

Second, be cool with being emotionally volatile. Normally, I’m pretty even tempered. During reinvention, my highs were higher, and my lows were lower. I may have even cried once while I was watching Parks and Rec (what?).  If you notice yourself swinging between the extremes, don’t worry; it’s a normal part of the process. My hope is that you reach out to someone who loves you when you’re feeling low.  


Still on the fence?

If you made it this far and you’re still on the fence despite being excited about reinventing yourself, I have one last piece of advice for you: go create an inflection point. Start now.




  1. Burning your ships refers to an old war strategy. Supposedly some generals ordered their soldiers to burn the ships they all sailed in on before attacking the enemy. This would leave the soldiers with only two options: win the battle or die trying. It’s not clear if this ever actually happened, but it’s a clever idea all the same. For our purposes the goal is to eliminate anything that might hold you back from success.

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25 thoughts on “How I transformed my life: a guide to personal reinvention

  1. Great story Jason, actually right now this article comes in handy for my current situation. I returned to my home country, I´m fine but my mind still misses everything I had. 99% of the thing you´ve mentioned are happening to me now, so thanks a lot, it really helps.

    1. So glad to hear it resonates, Richar, thank you for letting me know. 🙂 And wow, when you say that your mind still misses everything you had, I know that feeling well. The process of reinvention is pretty damn intense. In fact, it’s so intense that most people will never actually do it, even if they could benefit a lot. I’m glad you’re on your path my friend.

  2. Enjoyed every bit of reading this, and a little bit uncomfortable too. Even better. Thank you 🙂

    1. Wow. Thanks, Cindy. I really appreciate that! And hopefully it made you uncomfortable in a good way and that the discomfort translates into action.

    1. My pleasure, Becky! And yes. I feel substantially more aligned with myself than I did in the past. 🙂

    1. Thanks, Joseph – I really appreciate that. 🙂 And you’re totally right. People do hold onto lives that no longer serve. I did for ages.

  3. Glad to see you have found what many of us in Colorado know! Please don’t reveal why this is such a great place to live. It snows all of the time and winter never seems to end.

    For those getting rid of clutter and things in their life I would recommend the KonMari method of getting rid of clutter. Great books! Great psychological clearing to go with the elimination of so many possessions.

    1. Hahaha, thanks David. And yes, to be clear: Colorado is a terrible place. We get over 300 days of cloud cover, the people are grouchy and pessimistic, and it’s basically an Arctic tundra. 🙂

      I’m not personally familiar with the KinMari method, but I’ve heard great things. And I’m with you: getting rid of the physical stuff you don’t use is an amazing way to create more psychological clearing. Thanks for reading.

  4. Quit my job, traveled the world, came back, and now working on my own projects. I like that I have a term for it now. Massive INFLECTION POINTS!

    Thanks dude. I just found your site today and it’s awesome. Feel like I made a new friend!

    1. Hi friend! Good for you for being so wildly bold as to quit your job, travel, and then pursue your own projects. I also have a strong feeling that you’re going to succeed beyond your expectations. It’s amazing how much better and more alive life can become when you find the courage to follow your path. I’m psyched for you. 🙂

  5. Wow.

    You are able to put into words what I am feeling right now. I’m currently at work, started reading your article, and as soon as I was done reading it finally struck me: I can’t work here. No plan B; I’m quitting my job by the end of June.

    Thank you so much for your words, they have made quite an impact. Now I’ll spend my time doing what I have dreamt about all my life: be a full time musician.

    Once again, thank you!

    1. Wow. Adam, from the bottom of my heart, thank you. Your note has made my day. I’m so excited for you. Trust that clarity that you’ve found in this moment. As crazy as it sounds, you’re right to quit your job next month and pursue what you love. It takes huge courage to do this, but with huge courage, comes huge rewards. If you ever think of it, drop me a line and let me know how it all goes for you. My expectation: it’s going to be amazing. BTW: whenever people do something as bold and exciting you are, other people will try to convince you it’s a bad idea. Ignore them. Stay true to you.

  6. Jason – just by you walking this path you’ve lit the way for others to follow that ‘nagging voice’. For me it was nearly 9 years ago and I couldn’t be happier I did. Well done. I miss you here around DC but I’ll be Denver in Oct 😉

    1. Yanik – great to hear from you. And also, thanks for the encouragement. I’ve found that when I have the courage to live authentically and out loud, “leadership” becomes nearly effortless. I didn’t know you had gone through a similar transformation. I look forward to hearing about that. Let me know when you’re in Denver. I miss our chats in DC too. 🙂

  7. Wow. Great post Jason. I was led to it by your email today “There is no path …”

    Spooky timing. But I don’t believe in coincidences.

    I’m not quitting a job, since I built a new company out of the ashes of the last major inflection point of my life in 2001 which was forced on me when I was fired in the middle of the dotcom crash.

    A traumatising bereavement, but looking back the best thing that ever happened. Plenty I can say about that …

    But I’ve created a new inflection point because I have to divorce my wife of 20 years and move to a new place. We’re just making each other desperately unhappy, and I’m fed up of this nonentity of a place I live in. UK is a big place, and so is the world.

    I’m considering going back to a place I lived in back in the 1980s, still got wonderful memories and a close friend there.

    I’m ready for these big changes, and all my family and nearly all my close friends know and approve.

    I have no idea where I’ll end up and it’s really exciting!

    – Business? Doing ok and plenty of scope to grow
    – Friends? Supportive and I’d like to see more often and have more
    – Love life? Non-existent for at least a decade (looking forward to a new one)
    – Mental health? Poisoned by a toxic partner
    – City? Get me out of here!
    – Reinvention? Been there and done that – I know I’ll survive and thrive
    – Ending a long-term relationship? 20 years of marriage and ready to move on
    – Staring a business? Re-booting it
    – Extended travel? Great idea!
    – Investing in myself professionally? Part of how I came to this realisation
    – Relationships? What’s the point of being with anyone if you don’t make each other feel good? (all my friends do)
    – Professional organisations? Hugely enriching
    – Possessions? Most could go in the skip, and I want new ones

    Thank you again for your story.

    1. David, I appreciate you sharing all of this with me. Thank you! It sounds like you’re on the precipice of some really good changes here. Stay true (and kind) to yourself, and my bet is that some amazing – AMAZING – things will come into your life. And I’m not sure I believe in coincidences either. 🙂

  8. Just ended my 25+ years of marriage, it is absolutely mind-blowing freedom to me!! You are right, sometimes we just dig in deep in our heels for no reason because we are mostly creatures of habits. My marriage was a burden that I carried for a long time, every year I told myself that when my youngest son became 18, I would walk…sometimes late last year, I asked myself, “Why wait? Why can’t I do it now?” – well then, I did.

    I am not here to encourage people to not try to make marriage work, or making things work, or least, not making your best effort. As you mentioned, there is always that voice inside you prompting you to think things beyond what you are willing to settle.

    I am slowly making changes in my life and I don’t give myself any timeline but with only end goals in sight, aka, “I” need to be happy with the end result, so I take my time. I enjoyed this article for the simple fact that I know someone else out there has listened to that little voice and created a brand new life for himself. Thanks for sharing.

    1. Crystal – first of all: CONGRATULATIONS! That’s a bold, dramatic, and from the sounds of it, ultimately healthy change you’re making. Congratulations. You’re wise to listen to that little voice. You’re wise to be true to yourself. It sounds like you’re stepping back into the true you. Enjoy the changes and chaos and the beauty and the turbulence. Honored to have been a small part of your path.

  9. Wow just amazing. I felt a jump in my belly the kind I feel when a pastor was speaking as if he was talking to me. The only thing I am stuck on is my job as a mom. My sons are 21(who is out the house) 19-18 who are not out but under my roof and on my heart. I want to do a lot of what u have written but I feel I am a mom. Where do the lines start and in for mothers who feel it in the deepist part of me I need to run and go far. I am disabled in a wheel chair and on good days I am walking in a walker. My sons at as if they are grown men and don’t need me unless their hands are out. When can I pull my hand back and move own . I was a single mother from the start no one has ever kept them it was us 100%. Now it’s like I’m in the way.

    1. Hi Beflossy! I’m wildly honored to hear that this made your belly jump like a pastor speaking just to you. 🙂 First of all: I really admire you. Being a single mother is difficult and beautiful work. Big picture: if you feel the need to travel, then I URGE you to travel. I can tell that you’re a smart capable woman. You’ll be able to make it happen even while you’re still a mother and working with a wheel chair / walker. A bit more strategically though, consider working on this project one step at a time. Maybe your first step is to take a long weekend trip somewhere by yourself. Maybe somewhere you can go on the bus or with a quick flight. See how it goes for you, and for your sons. If it goes well, you can take longer and longer trips. You don’t need to make huge changes all at once. It’s truly amazing to see how dramatically life can change if you just make slow but steady modifications. Good luck, and let me know how it goes!

    1. And a good question, at that, Michelle. I think the best thing you can possibly do is play the card’s you’re dealt. I was in my late 20’s, single, and had a bit of walking around money when I did all this stuff. With a kid, I think I’d begin by asking, “What is the singular thing I can do that will make the biggest difference for me?” It may be moving to a new city, starting therapy, taking a vacation, whatever. From there, I’d break it down into small steps, and start taking action.

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