The Messy Middle: What No One Tells You About Career Transitions
from the founder of careercoaching.ie
I’ll never forget sitting at home in June 2021, knowing I was going to leave Facebook but not yet ready to tell anyone.
From the outside, everything looked perfect. Nearly 12 years at one of the world’s most influential tech companies. A career trajectory that had taken me from working with global brands to leading teams and product marketing strategy across EMEA.
But inside I felt like I was standing at the edge of something unknown, trying to convince myself to jump.
This is the part of career transitions nobody talks about. We celebrate the announcement. We toast the new beginning. But that space in between—where you’re neither here nor there, where doubt creeps in at 3am—that’s where most people get stuck.
Having coached many professionals through career transitions and navigating several of my own, I’ve learned something important: the messy middle isn’t a sign you’re doing it wrong. It’s proof you’re doing something meaningful.
Why Transitions Feel So Disorienting
When you’re in the middle of a career transition, you’re not just changing jobs. You’re changing identities.
For years, you’ve introduced yourself a certain way. You’ve built expertise that gives you confidence. Then suddenly, all of that gets questioned.
During my own career transition to becoming a qualified coach, I had moments where I genuinely didn’t know how to answer “What do you do?” My old identity didn’t fit anymore. My new one hadn’t fully formed.
Here’s what I’ve learned: this discomfort is necessary. You can’t become someone new while clinging to who you were. The messy middle is where transformation happens.
The Three Phases Every Transition Moves Through
Phase 1: The Ending
You recognise something needs to change. Maybe you’ve outgrown your role. Maybe your values have shifted. Maybe the work that once energised you now drains you.
The mistake people make here is rushing through this phase. They want to immediately jump to the solution—the new job, the career pivot, the next chapter. But endings require grieving, even when they’re your choice.
When I left Meta, I had to acknowledge what I was losing: the prestige, the financial security, the identity I’d built over more than a decade. Until I named those losses, I couldn’t fully move forward.
What to do:
Write down everything you’re leaving behind, both good and bad
Talk to someone who understands—a coach, a trusted friend, a mentor
Stop pretending you’re fine when you’re not
Phase 2: The Neutral Zone
This is the messy middle. For most, the hardest part as there isn’t an obvious action attached. You’ve left the old behind, but the new hasn’t fully materialised. Nothing feels certain. You question your decision daily.
I spent months here. My coaching training was underway, but I wasn’t fully qualified yet. I had left Meta, but I hadn’t yet built a practice. I existed in limbo.
Here’s what I wish someone had told me: the neutral zone isn’t wasted time. It’s where you discover what actually matters to you, stripped of all the external markers of success.
What to do:
Create small experiments—take a course, have informational interviews, write about your ideas. You don’t need a five-year plan. You need the next obvious step.
Find your anchor—one practice that stays constant while everything else shifts. For me, it was my coaching supervision sessions. Yours might be a morning routine, a weekly call with a friend, an exercise practice.
Talk to people who’ve done it—the best antidote to feeling alone is connecting with someone who’ll say “Yes, it felt like that for me too.”
Track the small wins—keep a record of the moments that gave you clarity, the days you felt excited, the realisations that changed your thinking.
Give yourself a realistic timeline—career transitions take months, sometimes longer. Having a realistic timeline removes the daily panic and lets you focus on the work itself.
Practise self-compassion; this phase is supposed to be uncomfortable
Phase 3: The New Beginning
This doesn’t arrive with fanfare. It emerges gradually as you take small steps forward.
You start to feel more confident in your new identity. The work begins to feel less foreign. You realise, almost without noticing, that you’ve become someone slightly different.
For me, this happened when I started calling myself a coach without immediately following it with my Meta credentials. When I could talk about my business without feeling the need to justify it.
What to do:
Acknowledge how far you’ve come
Share what you’re learning—blog, LinkedIn, conversations
Help someone else who’s in the messy middle
What Keeps People Stuck
Waiting for perfect clarity before taking action. Clarity doesn’t come from thinking harder. It comes from doing something, seeing what happens, and adjusting. You need 60% certainty to move forward, not 100%.
Comparing your middle to someone else’s highlight reel. When you compare your behind-the-scenes to everyone else’s showreel, you’ll always feel like you’re failing.
Trying to skip the emotional work. You can’t logic your way through a transition. There’s grief, fear, excitement, and uncertainty all mixed together. Until you acknowledge those feelings, they’ll keep you stuck.
What’s on the Other Side
I won’t lie: the messy middle is hard. There were days during my transition when I questioned everything (still do!). Days when I missed the clarity of my previous role. Days when I wondered if I’d made a terrible mistake.
But here’s what I found: work that feels purposeful. A business I built from scratch. The privilege of supporting others through their own transitions. A life that aligns with my values, not just my CV.
And here’s what my clients have found: roles that actually fit their strengths. Career pivots that reignite their passion. The confidence to negotiate for what they want. Clarity about what matters most.
The messy middle isn’t where transitions fail. It’s where they succeed—if you’re willing to stay in it long enough to do the work.
The question isn’t whether you’ll get through it. You will. The question is: what will you discover about yourself along the way?
Catherine