Why Even Confident Coaches Get the End-of-Year Scaries — And What the Research Says About It
Every once in a while an Anti-Boring Learning Lab member posts something in our chat lounge, and it takes off like wildfire. Last week, this post did exactly that:
"Every single year around this time, as I start wrapping things up with students, my brain suddenly becomes deeply suspicious that no one will ever return for coaching again.
After almost 10 years of coaching… Despite the fact that the majority of students do return each year… And despite the fact that the students who don't are usually graduating or genuinely ready to move on… My self-worth still seems to go: 'Okay but what if this year everyone realizes you're actually not that helpful?' 😂I'm mostly just fascinated by how predictable this little end-of-year spiral has become. Apparently, my nervous system likes this annual tradition.
I am not looking for advice, reassurance, or explanations for why this happens. I promise I already have plenty of thoughts circling around about it. I'm genuinely just curious if other coaches experience something similar this time of year."
The replies came fast. No advice, just as she'd requested — and so much empathy.
"Right there with ya."
"It's happening to me, too."
One coach, thirteen years in: "Every year for 12 years! A little more worried this year with the economy."
Me, too — back when I was seeing a full roster of clients regularly!!
One thing worth noticing: the original post isn't about whether it's actually true that clients won't come back. Back when I was coaching, I'd usually have most of my clients commit to the fall before the school year even ended.
These thoughts aren't about reality — they're the fears that show up at this point in the school year, whether or not the evidence supports them. The coach who wrote the post knew her thoughts were reacting to the transition. She wasn't confused about whether she actually had clients returning. She was just fascinated by the fact that her brain didn't seem to care either way.
Why student coaching hits different at the end of the year
I love that this conversation had so much traction, because it points to a very real experience for those of us who are self-employed academic coaches. And not just any coaching — coaching students, who follow the school calendar almost without exception. That means every single client you have is on roughly the same schedule, and in June, they all reach the edge at once. There's no steady trickle of arrivals and departures the way there might be for a life coach or a business coach.
There's a hard stop at semester's end. And then a summer of what feels like not knowing. And then — fingers crossed — a September.
When you're running a private practice, your income, your identity, and the rhythm of your year are all wrapped up in that cycle. This time of year, all three go wobbly at once. It turns out this happens at every stage of the career, whether someone's brand new or has been at it for over a decade.
Seeing how many student-facing coaches agreed with her, I couldn't help myself — I had to investigate my favorite question: what does the research say about all of this? I got curious and went digging. It's quite interesting! I hope she'll forgive me for ignoring that part of her request.
Looking back at the thread, the responses actually clustered around a few different things. Not every coach was reacting to the same thing — they just all recognized the feeling. Here's what I noticed:
Some coaches named the transition itself — the disorientation of the school year ending and summer stretching out ahead with no clear shape yet.
Others pointed to the financial reality: income drops in summer, and that's a genuine stressor, not just a mindset problem.
And one coach, in a follow-up conversation, named something more specific and more personal than either of those — the re-enrollment conversation itself.
Three different flavors of the same end-of-year moment. Here's what the research says about each one.
What the research says about transitions (and why self-employment makes them harder)
One coach who spoke up named transition itself as the bugaboo:
"Weirdly, it reminds me of post-show blues I used to get when a theater production ended. So much energy, structure, creativity, anticipation, and connection goes into a school year… and then suddenly there's nowhere for all of it to go."
That's actually a pretty good description of what organizational psychologist William Bridges spent decades studying.
In his Transition Model, first published in 1979, Bridges identified three stages of transition: Endings, the Neutral Zone, and New Beginnings. And notably, he was deliberate that transition starts with an Ending — not a pause, not a beginning. You have to move through the loss of the old structure before the new one can take shape.
The middle stage — the Neutral Zone — is the hardest. It's the in-between: the old structure is gone, the new one hasn't started yet. There's nothing to push against, nothing to anticipate. Anthropologists call this kind of in-between space liminal — from the Latin for doorway. You're standing in the threshold, neither in nor out.
That Neutral Zone is May-June for a lot of coaches.
The financial reality makes it worse
And here's what makes the transition worse for those of us who are self-employed: the Neutral Zone isn't just emotionally uncomfortable. For us, it's financially relevant.
Unlike for teachers, who are often paid throughout the school year, for coaches, income can drop off significantly for a few months.
A drop which, understandably, is a stressor! A 2015 study of people running one-person businesses by Schonfeld and Mazzola found that income uncertainty was a "common background stressor" — not an occasional crisis, but a constant hum underneath the work. When transitions hit, that hum gets louder.
The good news is there are concrete things you can do about the financial piece. A few options we cover in the Rock Your Biz Resource Library include:
Offer special summer coaching packages that solve real problems students need solved before the school year starts again
Raise your rates and charge in packages, so that you are well compensated for your time during the school year
Practice bookkeeping routines — I personally love the software You Need a Budget — so that you have money set aside when summer hits
All of those are possible. But even when these practices are in place, the sneaky goblin thoughts about "will I have enough money?" still come into play for many coaches. It's a real stress — and the practical preparation only gets you so far.
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resources, training, and connection with coaches who get it.
One more factor — and it's the most personal one yet
After the initial post, I had a follow-up conversation with the coach who started the thread, and she offered some nuance worth sharing.
She noticed that a lot of the replies from other coaches landed on transitions being hard, or on the financial uncertainty. But for her, it wasn't about either of those things, exactly.
The reason this time of year is hard, she said, is that she has to have a version of the same conversation with every single one of her clients, asking them, "Are you coming back?" Over and over. Waiting for them to abandon her, or accept her. Which one!?
Attachment dynamics are usually talked about in the context of parenting or romantic relationships. But they show up in professional ones, too. Recently a Lab member of several years told me she needed to leave. It was hard for her to say, and equally hard for me to hear. I was gracious about it, of course. But it was also painful.
It turns out there's actually some research on this.
John Bowlby and Mary Ainsworth, the psychologists who developed attachment theory, described the concept of a "secure base" — a consistent, available presence that others can count on to show up. For most of the year, that's exactly what coaches are for their students. But at re-enrollment time, something shifts.
A 2017 paper by Cheri Marmarosh published in the journal Psychotherapy found that endings in helping relationships stir up attachment feelings not just in clients — but in helpers, too. Although this research is about psychotherapists, I think it’s reasonable to extend it to academic coaches and tutors, too. Endings with our clients inadvertently stir up our own personal histories of intimacy and loss.
For this particular coach, the actual thought that plagued her was not simply, "what if fewer clients come back this year?" but rather "what if they realize I'm not actually helpful?" Ouch! Her brain jumps straight to self-blame. Sounds like her attachment system gets triggered — does yours, too?
When really, there are all kinds of legitimate reasons why clients don't come back that have nothing to do with the quality of the coaching:
Students get what they need and move on.
Families hit financial hardship.
A student needs to pause to focus on mental health.
Someone graduates.
As one coach put it: "Sometimes it feels like there are more reasons for people to leave than stay." That's not catastrophizing. That's just an accurate description of how this kind of work goes — and it makes the uncertainty real, not imagined.
One thing I know to be true (and it sounds as if the coach knows it about herself, too) is that she is most certainly helpful to her clients. This repetitive thought that comes up at the end of the school year is so understandable — a demonstration of how naturally attachment feelings arise at this time of year, with all the other uncertainty and in-betweenness this season offers.
Why the thought comes even when you know better
Why the thought comes even when you know better
Here's the thing: knowing why something happens doesn't stop it from happening.
We've just looked at three very good reasons why this thought shows up — the disorientation of transition, the financial reality of self-employment, and the attachment feelings that get stirred up by re-enrollment conversations. Understanding all of that doesn't make the thought stop coming. Your brain responds to present cues — quiet inbox, lighter calendar, unanswered re-enrollment conversations — regardless of what the last ten years looked like.
The thought showed up this week for coaches with nearly a decade of experience and coaches with thirteen years. It showed up for a coach in her first year of full private practice. Different experience levels, same visitor, right on schedule. That's not a sign something is wrong. That's just June.
The coach who started this thread modeled something worth naming: she knew exactly what she needed, and it wasn't solutions. She needed to know she wasn't alone in it. So she said that — clearly, without hedging — and made room for other coaches to just say "me, too."
That's this community. Not a place where everyone has it figured out. A place where someone can say "my brain is doing the thing again" — and a dozen experienced coaches say "yep, right on schedule."
If you've been watching the Anti-Boring Summer Certification from a distance, this is what you'd be stepping into: a room full of coaches who are honest about what's hard, curious about their own patterns, and genuinely invested in getting better at the work.
And it’s not too late to join us.
Not ready to commit? Start here: antiboringlearninglab.com/resources
Your Turn
What do you notice this time of year — in your thoughts, your energy, your body? Why do you think those thoughts come when they do? And what habits or supports do you put in place when the annual visitor shows up? Drop it in the comments.