The Messy Middle of Career Transitions

February 6, 2023

It was early January 2023, and I had been reflecting on the “who” of “who I serve” in an effort to better define my career niche. And then, there it was. I was listening to the “We Can Do Hard Things” podcast when these words brought tremendous clarity:

There are too many before-and-afters in society today. Too many Ta-Da’s! Too few people are willing to share from the unfinished place: our messy middle. It’s a service to others to show up as you are, vulnerable, while going through it. [Paraphrase, We Can Do Hard Things Podcast]

Glennon Doyle, Amanda Doyle, and Abby Wambach

That was it, the synergies in my work are found in the messy middle of career transitions. The familiarity with this new term was immediate and strong, like meeting a person with whom you have effortless rapport. The messy middle is where I found my own answers and my associations with it are grit, grace and gratitude – not only at work, but in love, parenting, health, and other “hard things”. While I’d not enthusiastically signed up for these grueling periods, there was no question they were profoundly responsible for my growth.

What is the messy middle?             

It is in the crossing from one place to the next, emotionally, physically or mentally.

It is where the feelings can be brutal and scary, but lead to new levels of consciousness.

It is where we may feel stuck, hopeless, excited, and inspired. Or we may be numb, unable to access much feeling at all.

It is where we can’t see the forest for the trees.

We may or may not see the end; there may not even be an end. Maybe all life is some form of the middle.

It is where we may be actively battling demons, or letting light and kindness seep in.

It is where we aren’t fully recovered from the thing we’ve just ended. Mabe it’s not ended yet.

It is where confidence waxes and wanes, holding us back and pushing us forward like a propulsion ride at an amusement park.

It is where true understanding and compassion for self can be found.

It is where judgment is overpowering until we learn to recognize and challenge it. We learn to shift from judgment to discernment: am I safe, am I seen, is this good for me?

It is a hard part of the journey. There are no grand overtures of having crossed the finish line, there are no bows on stage, there is no Instagram picture of the dramatic transformation. They don’t arrive until later, and often in ways we don’t expect.

As an introvert and highly sensitive person, I’ve learned to hold emotion: my own, yes, but also those of others. I’d like to be the last person to leave the room when I can sense someone is hurting. My desire is never to “fix”, but to help you see you have your own power.

To be clear, I’m specifically working with those in the messy middle of their careers. I am not a life coach, although work is part of life and sometimes it can be hard to separate the two. Careers certainly have their own messy middle.

Where is the messy middle of our work?

It is burnout and working outside healthy boundaries.

It is the disillusionment of a career that student loans have funded and for which you feel very disengaged.

It is in the quiet quitting because your values feel distant.

It is wanting to be seen and also feeling like you must hide.

It is desiring leadership, but being told you aren’t ready for it.

It is NOT desiring leadership, but being told you must assume it.

It is being in social work, but feeling drained by your helping energy.

It is working 60+ hours to keep up with nothing other than your own expectations.

It is having a J-O-B, but wanting a career.

It is wanting to start a business, but lacking the confidence to go after it.

It is being in banking when your heart feels you belong in community development; or an account manager who wants to fly the friendly skies as a commercial pilot; or an engineer who dreams of coaching athletes.

It is working for one organization only to learn tomorrow that you now work for another.

It is trying to understand organizational culture – where you can fit in and stand out at the same time.

It is also applying for 50+ positions without confirmation that a human is considering your many gifts and talents.

The messy middle of work doesn’t only happen in the “middle” of your career. It could happen at any point in time.

What happens in the messy middle is nothing short of magical. It is where we figure it all out in brutal and beautiful ways. It is where we learn our WHO – who we are, who we’ve been and who we are becoming.

We tell ourselves that we wish we could fast-forward through this part of our lives. To do so would change our course; it would take us from the moments of sweating it out and feeling the centrifuge and the ridges of the experience. Those are the spaces where we gain our courage, strength and perspective.

I am able to fully appreciate the gifts of this time period for the discovery and peace they afford us. If you are looking to traverse the middle with a coach who will honor you and help you discover your resilience, creativity, and leadership, let’s talk. I’ll meet you in the middle.


Dedicated to incredible clients and friends in the middle