The Messy Mid-Term: What nobody tells you about career transitions and why that needs to change
My friend Jen and I were talking recently about the stretch of time between where we were and where we are now. She spent four months navigating unexpected time off between two companies, and then found herself positioned in another time of uncertainty. I spent twelve months on a planned sabbatical that looked intentional from the outside and felt like an emotional rollercoaster on the inside.
At some point in that conversation, we named it.
The Messy Mid-Term.
It is the space between the version of yourself that existed in your last chapter and the one you are building in your next. It is not a crisis. It is not a failure. But it is genuinely messy and most people are either not talking about it honestly or not recognizing they are in it.
What the Messy Mid-Term actually looks like
My sabbatical was not a clean year of clarity and intention. My confidence shifted. My plans shifted. What I thought I wanted changed more times than I would like to admit. I started businesses I did not expect to start. I leaned into AI in a way I never anticipated. I had conversations that reoriented everything and weeks where nothing seemed to move at all.
Jen's Messy Mid-Term had its own shape. Hers came with the specific anxiety of a layoff, twice, and the particular pressure of figuring out what is next when the timeline is not entirely your own. But she came out of it with more clarity than most people find in years of steady employment. She knows what she wants her work to look like. She knows what she is building her life toward. She did not get there despite the mess. She got there through it.
That is the thing most people miss.
The real risk in the Messy Mid-Term
The danger is not the uncertainty itself. The danger is what people do because of it.
When the mortgage is real and the timeline feels urgent, people make decisions from desperation rather than direction. They take fractional or consulting work because they need income, not because it fits who they are or what they are building. They say yes to work that does not inspire them and resent it quietly. They put themselves out there before they know what they are actually offering.
I have watched people do this. I have felt the pull of it myself.
Fractional and consulting work is not for everyone. It is not a backup plan or a bridge to something else. It requires you to be good at many things simultaneously: business development, client management, financial discipline, operational execution. Or to be honest enough about your gaps to invest in the right support. Being a sole proprietor means owning everything, and that is genuinely hard even when you are ready for it.
Going into it from desperation rather than conviction makes it harder.
A direct word to those in the middle
If you are in the Messy Mid-Term and you are considering presenting yourself as fractional before you are ready, I want to talk to you first, not call you out.
Because the instinct is understandable. The bills are real. The gap on the resume feels uncomfortable. Fractional sounds like a legitimate bridge. And in some cases, it is.
But there is a difference between being honest about where you are and overstating where you have been. The fractional market is still maturing and the bar for what "fractional COO" or "fractional anything" actually means is being set right now, by the people doing it. When someone misrepresents their experience, takes on work they are not ready for, and delivers below the standard, it does not just hurt their client. It makes the entire market harder to trust.
If you are not sure whether you are ready, that is actually a good sign. It means you have enough self-awareness to ask the question. That is where the real work starts.
Getting clear on what you actually offer, who you offer it to, and how to position yourself honestly is not a sign of weakness. It is the foundation of building something sustainable.
That is work I help people do. If you are in this stage and want to figure it out properly, I would rather help you get it right than watch the market get it wrong.
A note for the companies hiring fractional talent
Not all fractional is the same. And this matters more than most companies realize when they are evaluating who to bring in.
The fractional market has grown fast. So has the number of people entering it from the wrong place. Someone who took fractional work because they needed a bridge between jobs is a fundamentally different hire than someone who chose it deliberately, who built their practice intentionally, who knows exactly what they offer and who they offer it to, and who is energized by the work rather than just available for it.
The desperation does not always show in an interview. It shows up later. In the quality of the thinking. In whether they are fully present or quietly hoping for a full-time offer. In whether they treat your business like a client or a placeholder.
When you hire fractional, ask the question directly: why are you doing this work this way? The answer will tell you almost everything.
The right fractional hire is not cheaper or more convenient than a full-time one. They are more experienced, more focused, and more accountable, because they have chosen to operate this way and they have built their reputation on delivering results without the safety net of a salary.
Hire that person. Not the one who needed a soft landing.
What Jen and I both learned
The people who come out of the Messy Mid-Term well are not the ones who moved fastest or looked most put-together on LinkedIn. They are the ones who gave themselves permission to not have it figured out while still moving forward. Who stayed honest about what was working and what was not. Who kept asking the right questions even when the answers were slow to arrive.
For Jen, it was clarity about putting her family first, owning her schedule, and doing only the work that genuinely lights her up. For me, it was a third chapter built around solving problems that inspire me and people I actually want to work with, and a deliberate decision to not mistake busyness for fulfillment.
Neither of us arrived here in a straight line.
If you are in the Messy Mid-Term right now
Take a breath. You are not behind. You are not broken. You are in the part of the story that does not get posted on LinkedIn and that is exactly where the most important work happens.
Be honest about what is driving your decisions. Are you moving toward something or away from something? Are you building for the life you want or solving for the immediate pressure? Both are real. Only one will get you where you actually want to go.
The Messy Mid-Term is not the problem. Rushing through it without paying attention is.
