Log Entry: 2020-02-22

A number of years ago, in the midst of a particularly difficult psychotherapy session, my doctor said something to me that caught me completely off guard - and has stuck with me ever since.

I had just finished recounting something - maybe a story, an anecdote, or a description of a reaction I'd had to something that had occurred recently. I don't remember what led up to the moment.

All I remember is her tilting her head to the side, clearly working to maintain the requisite balance of professionalism and human empathy that is so crucial to doing well in the field of caring for people. I'd been in therapy and mental health circles long enough at that point to know something momentous was coming - and, thankfully, I had a strong enough relationship with this particular doctor to know it wasn't going to be one of the all-too-common "well, time to find a new shrink!" experiences I'd had in the past.

But even still, it floored me when, after an uncharacteristically long and thoughtful pause, she told me, "Your degree of self-awareness is probably the hardest thing you have to fight against, and probably the only reason you've survived through everything that you have."

Undergoing something like a transition is basically a completely immersive, inescapable, all-encompassing exercise in juggling self-awareness, while trying to develop new skills for dealing with so many things changing at once.

Some things seem to change too fast, and others can't possibly get done changing soon enough.

I've remarked, many times in fact, that I feel like transitioning in my thirties is actually pretty good timing for me. I've accumulated plenty of life experience and skills for managing stress, change, and uncertainty. In a lot of ways, the past year of change has only been different from the rest of my life in one major, defining way: this is the first time I've ever undergone drastic life changes that seem like they might actually stay stable now.

After moving homes seventeen times in my life, I now see no real reason to ever want to move again.

I've settled into a career I love and a position that continues to excite me and provide opportunities and challenges beyond what I ever imagined it could have.

Many things are still changing in my life, but many more are locking into place, and every time I ponder what's happening, all I can think is, I did well for myself with a lot of volatility and upheaval in my life; what can I imagine accomplishing with such a strong core of stability for the first time ever?


Looking over all the things that I've weathered in the past, it's sometimes tempting to wonder how things could have been different. And for much of my life, I spent excessive amounts of energy and generated endless angst trying to think about how things "might have been."

But now, having gotten a taste of what actual stability and certainty can do, I've simply stopped thinking of it that way.

At work, I spend a lot of time talking to people about problem-solving - looking at various challenges, things that have succeeded, things that have failed, things that need improvement. A sentiment that I draw on a lot in those discussions is best summed up as "I don't care why it happened; how do we make sure we can do it again (or not do it again if it was bad)?"

It often catches people off-guard at first. What do you mean, you don't care why?

But the phrasing is important: getting caught in "why" is usually a recipe for endless tail-chasing. "If this team had done X, if that hadn't happened at that moment, if only, if only, if only." This almost inevitably gives way to blame. "That team or person dropped the ball. That supplier is too hard to work with. Somebody broke a contract." And so on.

By framing the conversation around what we do in the future, it instantly transforms the tone of what can often be a nasty, mud-slinging meeting into a collaborative effort to fix things. It's the same set of problems to solve, but focused on action in the future. Just a change of tense and timing.

Don't tell me what could have been different. What will you make be different next time?


After the past year of personal rearrangement, I find it oddly comforting that techniques I've drawn upon for years in my professional life have formed the basis for re-establishing my life out side of work.

For three decades, as soon as I left the office, I didn't know what to do besides fret about what could have been different in my personal world. And now I don't care anymore.

If things need to be different, I go make them different. And I have an unspeakably wonderful network of people who can support those efforts - people to learn from, people to struggle alongside, people to try to help by relating what I've managed to learn so far.


Close to 14 years ago, I wrote something uncharacteristically vulnerable and personally revealing for me (at the time). I talked about the aspirations I had, how I wanted to change things, to improve the world, to fix what I felt like were serious problems. I had no shortage of things to do.

I just never did them. So in a late-night moment of exposition on the internet, I simply pleaded with the question, why?

It was only a few paragraphs, but the angst was palpable, and even now, reading the words is haunting. They feel like they belong to someone else (and in many ways, they did) and yet all I can think is I know how to answer your question.

At the time, I lacked both the situational stability in life, as well as the certainty of identity, to really do anything. I floundered, a lot, for many years on end, and somehow managed to occasionally do something that seemed to work.

The rest of the things - the failures - I got good at quietly burying. Until I was alone, late at night, trying to figure out what could have been different.


I've enjoyed rock climbing - both freestyle bouldering and basic belaying - for a long time. I love the analogy of a good climb. When you first start out, even a fifteen foot training wall can be intensely intimidating - it's a difficult physical challenge, but also a brutal mental challenge. If you get halfway up and get stuck, you have to let go and either fall onto the mats or trust the ropes to get you back down.

Bouldering routes are often even more intense for that - if you do get all the way up, you can rest for a bit and celebrate, but then you still have to get back down.

Climbing without experience and guidance can be treacherous - just like life.

To know if you can do a climb, you need a few key things: you need to know yourself, your body, your capabilities, and your mental limits. I've found many climbs physically trivial but mentally insurmountable. In a gym, you can benefit from the deliberate design of the courses, and advice from others.

Bouldering in the wild is a vastly different experience. You often find yourself attempting a climb that nobody present has ever done before. It becomes an exercise in improvisation - within the limits of yourself, factoring in the advice of anyone else around, can you piece together a satisfying climb?

Climbing alone is generally considered inadvisable, even for highly trained and practiced experts. The safety check of additional perspective is essential, even without the importance of having help in case something goes wrong.


When I first began climbing, I'd look at people effortlessly gliding across a rockface and wonder how they did it. If I could ever be like that. It was tempting to just walk away and say, "nah, I can't." Someone had to coax me into the first harness, talk me into that first short ascent. By the time I wrapped my exhausted fingers around the "success" marker at the top of that wall, I knew I was hooked.

(I'm still, all these years later, no good at it; but it's still a huge amount of fun.)

Knowing that it's possible is a big prerequisite. Someone else just climbed it, so clearly it can be done.

With help, practice, and training, that becomes something all of us can own: I climbed that one, so maybe I can also do this other one.

With any practiced skill, knowing that there is room to be better is important for motivating the desire to get better.


And life is really no different. There is so much room for things to be better.

The answer to my questions from 14 years ago is really the kind of thing that sounds so simple to say, but I suspect can't possibly really resonate without the first-hand experience of the life I lived in between.

Life is a climb, but there are resting points. There are hard routes and easy routes, and we don't always get to choose which ones we have to travel. The journey is never predictable and often hard and painful.

The good news is, we get to decide what we consider to be success. We get to decide who to take along for the journey. We get to seek traveling companions who can point out a quicker route, or a more interesting vantage point to rest at.

Know who you are. Know what you've got. Know what you can trust, and what to take with you.


And when you reach a resting point - on a small anchor drilled into the rock, or a tiny shelf, or a full-blown base camp with the comfort of a fire and a good night's sleep - take the time to think. Tell me your story of the preceding leg of your journey.

But don't tell me what could have been different.

Tell me what you will make different next time.