Identity Change and Optional Retirement

It’s been a bit since I’ve published, and I miss it! Running a school during pandemic times is really hectic, and I’m focusing almost all of my energy there until the end of this school year. The students need and deserve our focus right now. Then, I move into optional retirement!

As I’ve watched others hit their FI goals and transition to full retirement or career change, I’ve always enjoyed reading their exit posts. There are generally two themes – one is the sudden and dramatic exit and the energy around that. Unfortunately, that doesn’t happen with educational leadership.

The second theme is often about wrestling with, or preparing for, the identity change that comes with leaving a career. Wow – there is a LOT of that happening with my impending change. 

Since I’ve found value in this (both inspirational and philosophical) I’ve decided to share my experience about exiting from educational leadership after a 20 year career in the profession I love.

(Note: I do plan to write more about the financial moves we are making as my optional retirement approaches – but this isn’t that post.) 

No Dramatic Exit

One of my favorite things in the personal finance space is when someone makes the decision and shares out what it’s like to give notice. I still remember the live tweeting Stop Ironing Shirts did when he left. (Here’s a 2 year update from him- can’t believe it’s been two years already!) A Purple Life also shared about her exit while it was happening. 

An education administration exit is a *little* more drawn out if you’re doing it in the right way. I wanted to let my team know well in advance for several reasons. It provides lots of time to get hiring right, and allows for a successful transition. For many administrators, this means up to 6 months when people know you’re leaving but you’re still working full-time. 

I made the decision back in the fall, and then held it for a while. I notified the appropriate people in February. Then there was a multiple month hiring process! 

No dramatic exit for me – it’s more of a zombie-like shamble as people start to pay attention to the new boss coming in. 

Now that my successor has been named, people awkwardly wrestle with what to ask me, and what to ask the new authority. Fortunately, we’re working out a good transition process to make that clear to people. But, I’m “dead man walking” in many ways. I don’t mind – it’s allowing me to enjoy more of what I liked about the job from the beginning. 

It just doesn’t make for a good tweet storm!

Identity Shifts

The identity shifts required for optional retirement from a school principal career are something else! I’ve been reflecting on (and experiencing) a lot around this lately. I’ve grouped my thoughts into three different categories below.

Personal

It’s been said again and again that you shouldn’t be racing to retirement without knowing what you’re racing toward. Many have also cautioned that for consequential careers (like medicine) the change can have a dramatic impact on self-concept.

I’m fortunate that I’ve always felt my job mattered and has worth. Working in public education is as meaningful as it gets. I can quite literally help produce a more informed citizenry, give a student the path from poverty, or make a mistake that leads them to dramatically negative consequences (e.g school to prison pipeline). As a principal, I’ve been cognizant of all those things daily.

It’s also true that I’m known and active in the community. I have the pleasure of working with decision-makers at various levels of government, business, and community organization.

I’m walking away from all that.

I’m confident I’m prepared for it. There was a time in my life where I needed to feel important and known. That’s not the case any longer. I’ve been there, it has benefits and costs. Right now, the introvert side of me is craving a lot less of those things.

I’ve also become more clear about what work I find most fulfilling and interesting. It’s not leading others, engaging at political policy levels, or earning more money.

I’m looking forward to less notoriety and the ability to focus on smaller, more personal projects. After leaving my classroom to work at the larger systems level (school and district) I now want to spend some time working with individuals. 

By some measures I’ll matter less and I’m okay with that.

I’ve been surprised that my coming identity shift has had a larger impact on others…

Professional Colleagues

I’m fortunate to have worked in my community in a variety of roles for more than 20 years. I know many people, have a strong professional network, and have cultivated a strong group of peers and mentors. I’ve also hired, supervised, and supported 100s of educators and staff. 

I believe I have a strong reputation and am known for my passion for public education. To say my “sudden” departure had ripples among this group is an understatement. I had anticipated most of it, and have chosen not to be very public about the optional retirement portion of my exit. In education, people just don’t understand not living and breathing education. I like that about our profession, but it also has its problems.

Anyway – those I’ve worked closely with have had three primary reactions while wrestling with my choice and how THEY see ME. Some have moved through multiple phases, while others jumped straight to the last.

Shocked

Most readers have known me as the person planning for financial independence to gain security and choice. My professional colleagues know me as someone who lives, breathes, and sacrifices for education to the exclusion of all else. I’m often professionally described as “intense.” There are many, including some of my family members, who have said they love what I do, but would never want to work with me.

I’m also generally considered stable, calm, and strategic. 

For me to unexpectedly announce that I’m resigning after a decade of education leadership, and two decades in education, just didn’t fit with many of my colleagues’ concepts. The announcement shifted my identity FOR them. 

It’s been interesting to watch this reaction. The first question is always, “So, what are you doing next?” with the assumption that I’ve got some master professional plan that will take on more responsibility and have greater impact.

When I reply that I don’t have plans yet, but intend to pursue something I’m passionate about but is likely to be smaller they usually laugh, nod, and shrug. They flat out don’t believe me. It’s just not the identity they hold for me.

Abandoned

Similar to the first group, but with a variation. Many people count on me. I have a good reputation and there are a large number of people that have come to work at my school because the leadership and culture are viewed as solid and supportive. I’m also well known for sacrificing to ensure the safety and security of others.

For these people, me choosing to leave is abandonment that could destabilize their professional lives. This is something they don’t believe I would do. Unspoken is the belief that I’m selfish for not staying to focus on their needs.

I actually struggle with this one most, because I fear there is a kernel of truth here. I do feel a little selfish for stepping back when I know I have a positive impact. The fact that many of those having this reaction are people I trust and respect make this one difficult. When they say they’ll miss me, they mean it deeply.

These are also the people that tend to be most vocal and steady with their feedback about the change. I get almost daily requests from people to reconsider and stay. Or, if they’re also part of the first group holding onto the idea that I’m inevitably going to something bigger, they ask to be taken along.

The identity shift from “someone we can count on” to “someone who is letting us down” is the toughest one.

Moving On

I’ve been through professional transitions often enough to know many people jump straight here, while most others get here eventually – even if they really will miss you. The time of that shift is the only difference.

It’s a fact that no matter how much we are connected to other people, we also naturally think of ourselves. Some people, of course, think of nothing but. 

When I announced months ago that I was leaving, the first question I got from several people was “who will take your place?” They moved on instantly. I understand that and it actually doesn’t bother me. It’s no coincidence that these are generally people I haven’t connected with, or have expressed concern about. A few would like me gone yesterday. 

However, many more people have hit this phase since my successor was recently named. As the end of the school year approaches, we make many decisions about the next school year. People are beginning to awkwardly ask me questions while really wanting to know what the new person thinks. Some are starting to bypass me entirely when they can.

This is both an advantage, and disadvantage of the long drawn out process. People have come to terms with it. I am no longer identified with authority. Some have talked to me like a real person (instead of “the boss”) for the first time ever. This actually reinforces my decision to step out of leadership.

The downside of course, is the awkwardness. I don’t need people to pretend to care about my opinion or that I’m leaving. Many of them need that, though. This leads to long opening statements or frequent expression of their sadness that I’m leaving before getting down to business. 

This is not how I operate, nor is it an efficient way to get things done. We’ve got kids to focus on, not me. No matter how often I say publicly that I don’t need this, people continue to do it.

This is an interesting identity shift in itself. When I was “the boss” – they felt no need to safeguard my feelings. Quite the opposite. Now, suddenly, I’m about to shift to become a real person. They’re moving on, but don’t understand that I am as well.

It’s fascinating.

Others in Your Life

Perhaps the biggest surprise in all of this, are the reactions of those in my family and circle of friends. My shift from “someone who matters” to someone who doesn’t had a larger impact than I thought with this group.

I have friends who believe my professional influence benefited them. They aren’t usually crass enough to say this, but it shows up in some of our conversations.

Family members were proud to talk about my meetings with the mayor or how I was asked to help plan something in the city. I had one say, “But there will be no more articles for me to share with the cousins!” 

A very interesting, but not unexpected, set of questions comes from the older generations of my family. They are of the generation where work WAS identity. In one case, an uncle worked the same job for 40 years. He considers his retirement the worst day of his life, and has admonished me several times that I’ll regret having less structure in my life. 

Finally, perhaps the strangest reaction of all was someone who asked, “Aren’t you going to miss having people be afraid of you and having to listen when you tell them what to do?”

That one actually made me laugh (and glad that person wasn’t in a leadership role.) It’s just so far from the reality of effective leadership. Even were it true – I’ve never enjoyed mandate by pure authority. 

Family and friends will be supportive no matter what, but it’s been fascinating to watch them struggle with my identity shift.

Pondering What Comes Next

In less than two months time, I’m shifting from “passionate education leader” to a guy with no professional identity. I think I’m going to do well with that transition, but am open to the idea that I might not. 

I may really miss the daily interaction with students. (This is likely) I may miss the community visibility more than I expect. (This is very unlikely) I may miss something I don’t even realize right now. 

One of the joys of being financially independent and taking an optional retirement is that I can always go back. I’ve already had multiple job offers. There is a lot of work to explore. I’m also eager to have time to focus on learning new things entirely. That joy of focused learning is what drew me to education in the first place – and sadly something education leadership has limited for me.

My favorite shift is from “person who has to work for financial reasons” to someone who chooses based on passion, interest, and what matters. Things are changing, and I can’t wait to see what comes next.