How to Navigate a Big Life Transition
Just when our fairy tale seems poised to come true, a wolf shows up that threatens to destroy it; that’s okay. Because if you banish the wolf, you banish the hero. We all need to be the hero of our own story. That’s why we have fairy tales after all, and why we tell them year after year, bedtime after bedtime. They turn our nightmares into dreams.” — Bruce Feiler, TED Talk
You’re stuck in that awkward in-between phase in life. In-between jobs, in-between homes, in-between relationships, maybe in-between prisons. It feels like you’re between an old life purpose and your next one.
What do you do when you don’t know where you’re going next?
In this article, I write about how I’ve navigated my life transitions and touch the general framework of managing life transitions as researched by Bruce Feiler. I also share Bruce’s tips, as well as mine, to help you navigate your own life transition.
Five years ago, I decided to move from Toronto to a 20,000-person town in the middle of nowhere, specifically the middle of the sub-arctic, Yellowknife. Five years later, I made the same big decision to move back.
How to get unstuck
“If you’re going through hell, keep going.” — Winston Churchill
There have been many times in my life I’ve felt stuck. Just as everything seems to be going great, inevitably, shit hits the fan, and it’s back to the drawing board. As Mike Tyson said, “Everyone has a plan ‘till they get punched in the mouth.”
Bruce Feiler calls this experience a lifequake, a massive life disruption that shakes you to the core. Your life loses meaning and causes you to have to make new meaning out of your life.
Let’s rewind to about 6 years ago.
My writing and marketing career was struggling to get off the ground. I’d been making shit money writing content and ads for the most discerning businesses. And I was depressed. But I had some writing chops, a sharp wit and a stubborn determination that propelled me forward as often as it threw me back. I also joked that I’d never work a real job. When I found out about copywriting, it was holy matrimony.
I couldn’t afford to attend a fancy portfolio school, so I had to do it the long and hard way. Personally, I don’t recommend this approach. My advice: be born into a wealthy family that sets you up with a sizeable trust fund so you can skip all the reinventing-the-wheel bullshit in the middle.
Like many university graduates experience, to get a job, I needed experience and a portfolio. It’s like ordering an appetizer at a restaurant and the waiter asking how much food you have before deciding whether to serve you. So I made a profile on UpWork.
I landed my first client all on my own. My first SEO-mill article about different stock valuation formulas earned me a whopping $4. But I was proud of putting myself out there and earning money for myself, like a real entrepreneur.
Over the next year, I wrote all kinds of stuff for all kinds of clients — people, businesses, and publications. I interviewed gay porn stars and drag queens for a magazine, despite not knowing anything about either. I wrote articles about private jets and yachts for wealthy elites. I wrote an article for a pickup artist about body language.
Crossing the chasm
After freelancing for a while, a mentor connected me to the owner of an ad agency in Yellowknife. I expected the conversation to go like this: I ask questions about the industry and she gives me advice. But when I opened my email the day after, there was a tempting job offer in my inbox. I had a huge crossroads ahead of me.
Yellowknife was the last place I thought I’d move to— but then again, how many people dream of moving to a place with temperatures reaching below -40C, ~3 hours of daylight during the winter months, and located 1,600km from the nearest major city?
On the one hand, I needed experience — and money — and adventure is always enticing. On the other, what if I didn’t like it there or didn’t like the job and lost out on other opportunities?
I decided, fuck it. Let’s go. It beats bathing in cigarette smoke at my mom’s crib.
The three phases of transition in life
When you find yourself stuck, you need a transition—something you choose to get momentum going in your life. Many of these ideas come from Bruce Feiler, with my own experiences and thoughts added.
There are 3 stages to a transition:
The Long Goodbye
The Messy Middle
The New Beginning
They don’t necessarily happen in order, and we gravitate to the one we’re best at and usually get stuck in the one we’re worst at.
The Long Goodbye
I’m going to skip all the way to my transition back to Toronto, but if you want to read more about my life in the ‘Knife, I’ll write about it in a future story.
I was running front-of-house and marketing at a performing arts theatre. I’d been burnt out for a while but wasn’t aware of (or great at ignoring) it. Though my director, some of my volunteers and friends did.
I kept trying to power through burnout while feeling unmotivated, losing track of what mattered and just being kind of grumpy, overall. Listening to how I’m feeling is a constant sticking point. How could I talk about what I wasn’t allowing myself to feel?
Like many people, I was out of a job when the pandemic hit. It was the first collective lifequake.
I was stressed out about finding another job and spent a couple of months doing much of nothing during the lockdown.
Reevaluating my relationship with work
I had the space to reevaluate my relationship with work, my craving for validation from my career successes and my need to be responsible for significant things.
My self-worth was linked to how well I saw myself performing at work, and it hurt to my core when I failed. It created a feedback loop where feeling down about myself also brought down my work performance, further fueling the cycle.
I wasn’t sure of my skills and lost confidence in myself. I felt like a failure and kicked myself in the ass for not getting a safe, high-paying government job like my friends, who were still getting steady paycheques.
Do I even want to work in arts and entertainment?
Do I even like marketing?
What am I even good at?
These questions ran through my mind as I reluctantly began to accept that the life I had, wasn’t coming back. Even if the pandemic ended, the theatre wouldn’t be the same. I wouldn’t be the same. The world wouldn’t be the same.
Eventually, I got bored of sitting around and went to work at a homeless shelter with a buddy. Working at a homeless shelter in a place that gets below -40C regularly is an eye-opening experience. It wasn’t long before I was presented with a choice between two opportunities: government communications or a reviving marketing agency. I was torn, but perspective from an old coworker helped break the tie, and I went to the government.
It was a good job, and I loved my team, but when my contract ended, I still felt I was drifting around, out of place, not knowing where I was going. I knew for sure I wasn’t going to retire from the government.
Where do I go? Where do I even want to go? I struggled to answer these. Burnout, anxiety, and depression all make it harder to gain clarity. I decided to make 2022 the Year of Me and keep working on myself.
One of my best friends asked if I could make his bachelor party in New Orleans. I told him I wouldn’t dream of missing it. While booking my ticket, I saw every flight went through Toronto. Again, I had a crossroads. Fly back to Yellowknife or Toronto?
I chose Toronto. Now I had a definite date. I needed to accept that the life I wanted for me wasn’t possible where I was. That’s when I realized I needed to move on. Cue transition.
Now I could start working on the next phase.
The Messy Middle
Saying goodbye is tough. I had to say bye to many people I loved and wrap up all the things I needed before moving. I felt like I was spinning my wheels. I didn’t want to go, but I knew I couldn’t stay. There was something out there calling me, even if I didn’t know what it was yet.
You’ve probably had this fantasy while stressed out and fed up with life: packing up and moving to the place of your dreams, or literally anywhere else. While a fresh start can be a reset button for your life’s narrative, it’s not always the magic bullet you’d hoped for.
“Wherever you go, there you are.”
I keep this quote in mind and it’s been true every time I go to a new place with the expectation that things will be different this time.
When you’re stuck in old patterns of thought about who you are and what you can be (or not be), a change of scenery can inspire you to be the best version of yourself. The thing is, it wears off quickly.
Some people never realize this and jump from place to place, person to person, looking for the right environment that will solve all their problems. You still need to do the hard work—and it’s really hard—of letting go of old mindsets, beliefs and behaviours that no longer serve you.
You don’t need to move to do this, but in my case, the two went hand in hand. What surprised me was how after the novelty of changing cities wore off, I felt my limiting beliefs start to creep back in.
Before I could move to the New Beginning stage, I had to let go of mindsets holding me back from new possibilities. One technique I use to challenge limiting beliefs, is the George Costanza Principle.
Meeting new people and reconnecting with old friends made me realize that I set my own limits. They aren’t real. They’re just stories I’ve accepted as true and I can choose to tell new ones.
Now we can write a new ending to this tumultuous fairy tile.
The New Beginning
This is my favourite stage. One I’ve always been good at. I’m constantly reinventing myself, so it feels like home.
This time is different, though. I’ve done a lot of introspection to figure out who I am—what do I value, what’s important to me, who do I want to become?
I’ve reflected a lot on my strengths, flaws and what works best for me.
Here’s a non-comprehensive list of things I’ve tried:
- Therapy (CBT, IFS, EMDR)
- Psychedelics
- Meditation
- Journaling
- Values sort
- Men’s groups/workshops
- Personality tests
- Interviewing
- Deep life chats
I wish I could say I’ve figured everything out, but I’ve just started asking better questions. It’s one thing to know yourself; it’s another to apply that knowledge wisely in the context of your life.
It’s one think to know you can act like a total asshole in some situations, even why you’re compelled to act like one. Still, true wisdom is learning to avoid being an asshole in those situations in the first place.
Write your next chapter
Many times, I’ve been sure about what I wanted and when it didn’t turn out the way I’d hoped, I started to doubt my ability to choose what was good for me.
I had to start from the beginning. I’m in this phase now, where I’m starting new projects and telling people about them. Firing up my Medium account is one of them. My techno music is another. My freelance marketing consulting and copywriting is another.
I learned that I’m not doing things differently than expected. My problem was looking for the answer to what to do with my life, as if it were a multiple-choice exam question. It’s really about finding confidence in myself to navigate challenges, and trust my ability to figure things out, grow and do great things.
What’s changed most is the story I’m choosing to tell. I can choose to focus on the grim, painful, depressing parts, or focus on the inspiring, loving and beautiful parts.
What parts of yours will you focus on?
How to navigate a big life transition
Now for the practical advice on how to navigate a significant life transition. Again, many of these ideas are from Bruce Feiler’s work, so check him out if you find this interesting.
1. Start with your superpower
Being in that messy middle, not knowing what’s next, can make you feel like you’re not good at anything. Your inner critic’s volume turns up as your confidence plummets.
This is where you go back to what you’re uniquely great at, your superpower.
If a life quake is a physical blow that knocks you on your heels, a life transition is bouncing off the ropes back onto your toes.
The key here is to build up your confidence and get momentum going in your favour. I gravitate to writing, making music and reconnecting with friends.
I struggle to express myself and take up space whenever I’m feeling shame from not being sure about what I’m doing, where my career’s going, or what I’ve achieved so far. So creating and sharing things from the heart is the best way to move through this feeling.
Most people at this stage do 2 things:
- Make a 200-step to-do list and try to bang it out in a weekend.
- Lie in the fetal position and say they’ll never get through it.
I’ve tried both and wouldn’t recommend either.
2. Face your feelings
The first and most challenging thing you have to do is accept that the transition you’re going through is an emotional experience.
What’s the biggest emotion you’re struggling with during your transition? Is it fear, sadness, shame, guilt, anger, or loneliness? How can you cope with these feelings?
About 80% of people use rituals to cope with these feelings. Some sing, others dance. Maybe you want to hug it out with someone. Rituals let us be vulnerable with others and remind us we’re not alone in the struggle.
I mentioned earlier about how I write, make music and spend time with friends to navigate these icky feelings instead of suppressing them until I have an emotional breakdown. Those are my rituals. What are yours?
Expressing vulnerability is powerful because we share the burden with others, allowing others in and letting us sit with those uncomfortable feelings.
They also contextualize our experiences as milestones in life—like prom or graduation galas to celebrate the closing of one chapter and mark the transition into a new unknown.
Rituals are potent in the Long Goodbye phase because they’re messages to ourselves and others that we’re going through a difficult time and we’re ready for what comes next.
3. Try something new
The Messy Middle is, well, messy. It’s disheartening and disorienting. We need to find our bearings, but where do we start?
Anywhere. What have you always wanted to do but couldn’t do because you were busy with work or school? Start there.
Digging lots of little holes will help you find what’s next for you. Open two-way doors where you can start a side project that doesn’t lock you out of pursuing other opportunities.
I tried cold plunging which completely shifted how I feel and see myself and inspired me to connect with others.
We do 2 things when we’re spending time in the wilderness of the Messy Middle:
- Shed mindsets, routines, habits, and parts of our personalities, like animals who molt. Shedding lets us make space for what comes next.
- Commit astonishing acts of creativity.
We have to let parts of us die to create a new life. This is where pain and discomfort thrive, but it’s part of the transformation process. You’re a freaking phoenix. Are you going to rise from the ashes or burn out?
Psychologist Kazimierz Dabrowski’s affirms in his theory of Positive Disintegration, that pain and discomfort are necessary to experience personal growth, to fully integrate one’s experiences and adopt lasting personality changes.
Once we’ve created that space for new experiences, the best way to realize those changes is to give birth to something new, literally creating a new self. There’s a simple and elegant magic in creating something from nothing.
We’ve all seen the baking pandemic cliche on our Instagram feeds. Simply imagining a rising loaf, a painting coming to life, or a poem blossoming from a beautiful thought lets us believe we can create a new self.
4. Get advice from others
I do this all the time. The hardest part of a life transition is going through it alone. Especially when all you see on social media are highlight reels from people you follow.
The pain of transition is hard enough, but we love to torture ourselves further by comparing our lives to other people’s and facing the pain alone. I struggle to share my pain, so writing this is my way of announcing that I’m going through a tough change and I’m ready for what’s next.
Let people know what you’re going through, and you’ll be amazed at the ways people show up to help.
I’ve been meeting with people as part of my 50 Coffees project. I gain insight from inspiring people and share the burden of my transition to boot. Win-win.
5. Rewrite your life story
At its core, a life transition is a meaning-making experience. What are you telling about what your story has been and where it’s going?
Get autobiographical. This is your call to revisit, rewrite, and retell your life story and add a new chapter about what you learned during this transition. No matter how bleak your story has been, you can’t give up on a happy ending.
Only you control the story you tell about yourself, even the most painful parts. It’s your choice to write a different ending if you don’t like where your current one’s headed.
That’s why we have to look at life transitions as healing times that take the wounded parts of our lives and start doing the work to fix them.
How will your story unfold from here?
