The best worst year

Hi everyone.

Me again.


Today is my first day back at “home” after my yearly holiday trip to Iceland, and I am going to spend some time reflecting on 2019 like I do every year!

Follow up from last year

Body modifications (orchiectomy) ✔️

I did it. This entire process was one of my biggest trials of the year. Seriously, this broke me to my core. I might blog more about it later, but to put it into perspective the actual physical task of slicing my balls off was the EASIEST part of this process.

Body modifications (breast implants) ✔️

Oh fuck yes. Best 10k I ever spent. You should do this.

Learning Icelandic ✔️

This should really get like 1/2 a check. I am very far from fluent. Yesterday I was able to have a very long conversation on the Icelandair flight and make a new friend – without crafting a single English sentence. Although I did ask how to say certain words from time to time.

Eat more plants ✔️✖️

I get a check for half the year. Once things got rough with work my diet went to shit.

Write more books ✖️

Nope. Not even close.

Climb more mountains ✖️

I am also giving this one a no. I talk more about it later, and despite completing some of my goals this was a big part of my year. Read on to find out more.

What about this year?

To get started here is a master list of notable events in my life for the year.

  • I quadrupled my salary and make more money than I ever have made in my life
  • Then I threw it all away
  • I took significant time away from work for the first time in my career
  • I moved to a new house in San Francisco from Seattle
  • I gave a car away
  • I bought a new car
  • I left my fiance
  • I started a new job
  • I became an aunt

So – you know – another unexciting year for myself.


So there have been a few topics on my mind recently, and I have spent the past few days boiling these down into a few common themes. Hopefully I can use my experiences listed above, to talk more about the lessons I learned this year.


Lose noun: be deprived of or cease to have or retain


So 2019 hands down as been one of the hardest, and most challenging years in my life. Mostly because I was hoping to recover from 2018 but the universe had other plans.

And no I am not trying to have some giant “pity party” but it’s been hard. After Charlie died I didn’t think I would be able to move on. I found solace, safety, and hope in a few other elements of my life.

  • My job in Seattle
  • My fiance Callie
  • My house in Seattle
  • Mountains of course

All of these came to a sudden and unexpected end in 2019.

The first one of course my job in Seattle.

I decided not to say much here, other than it was hands down the best job I have ever had in my life.

I try to not live with regrets, but I wish I would have cherished it more while it was around. So that’s my first takeaway for the year.

Remember to love what you love while you still can.

As work stopped, I decided to spend some time focusing on myself. Then is when I noticed that I had lost my drive to climb. I can’t explain it, something just SNAPPED one day. I found myself sleeping in parking lots without the motivation to get started in the morning.

In retrospect I think it was the stress of losing a job (and therefore needing to find another) that pulled me away from mountains.

For instance, while traveling in the arctic circle with my fiance Callie last year the anxiety of a new job was so overwhelming I couldn’t even enjoy our trip. I had to come home early… to put it mildly.

As Callie and I drifted apart I realized a lot about the relationship, and myself. Primarily that my love for this world is based a lot on safety and trust. All of which I lost with both Callie, and with work. So that’s the next lesson.

If you don’t have trust, what do you have?

So I focused on finding a safety net. I landed a new job at Sysdig that I am very excited about. I started the move from Seattle down to San Francisco. My alpine tools went into storage, and have been there for months.

This year has been very hard for me.

But it’s made me stronger.

This isn’t necessarily a new lesson for me, more like a friendly reminder.



Resentment noun: bitter indignation at having been treated unfairly


This word fucking terrifies me.

So it’s very easy to remind yourself that life isn’t fair… or that bad things can happen to good people. Regardless of how you view the feeling, it still is a very authentic and true feeling.

Between losing Charlie, my bio family, even giving up my old life in Colorado to move to Seattle there was a lot I was bitter about.

Even simply being born transgender has made me resent the world, but I try to make the best of what I can.

There are a number of little things that have broken me down. Everything from a moving company withholding my items from me for over a month (hence my workspace pic) to losing some friends on Mount Rainier earlier this summer.

Work, Open source, bills, my life with Callie, my car, dealing with a lawsuit, the list goes on and on. I found myself beating myself up and resenting myself. Here is what I learned:

It’s not you

The world fucking sucks, but that doesn’t mean YOU suck.

Good things leaving you can be just as unexpected as bad things entering your life.

Resentment is very dangerous

but we all still feel it.

So my takeaway here is that when there is loss, naturally there is resentment. I try to remind myself of this. Both for my own forgiveness, as well as for forgiveness of others. Sometimes shitty stuff happens, and that’s just part of life.

Forgive me.

I’ll forgive you.

We all feel it.

But most importantly

Forgive yourself.


Next year I want to get better at dealing with this. So let’s check in next year and see how we are doing.


Hope noun: a feeling of trust, or a desire for something to happen


I don’t know which mountain I will climb next.

I don’t even know when I will see my mountain climbing tools again.

I don’t know when I will have a bed.

I don’t know when the next bad thing will happen.

I don’t know if I will ever see Callie again.

I don’t know what will happen in 2020.



Regardless I am so happy, and so grateful for everything I have in my life. Even if it’s just a laptop, a blanket, and a diet coke.

I have found love in places I never thought I would. I have felt more pain this year than I ever thought I would feel in my life.

I wasn’t ready for any of it, the good, the bad, the unexpected.



Regardless, I am so hopeful that having made it through another year that has tested me and given me valuable tools I will be much stronger for 2020.

I laughed this year.

I made new friends.

I pissed old friends off.

I went on new adventures.

I cried.

I fell in love.

I was heartbroken.

I was scared.

I lost.

I resented myself.

I found hope.


In summary I think this was the hardest year I have had in a while, and maybe in my life. I can’t explain it though, I am glad it happened. It has me ready for a new chapter in 2020. I loved this year, even though I also hated it. I feel like maybe this is the year I actually finally grew up?


Which makes this…



the best…



























Goals for next year



I don’t know how to describe this yet, but I want to get back out there again. I will know it when it happens.


Be a good boss

I have an opportunity at my new job to inspire and lead others to greatness. I really want to understand the folks who I work with, and spend time figuring out ways to lead them. I definitely don’t want to be “be the boss I never had” but maybe be the “boss they need to be great“.


Create something

I haven’t completed a project, or built something new in ages. I think I miss actually building things. This year I would like to create something I am proud of.


Love myself

Forgive myself for resenting things, and manage the feelings in a healthy way. Forgive others for resenting me, or other things in the world. Ultimately I want to be a good partner, boss, and leader for everyone in my life – but mostly for myself.


Sleep more

This is a big one – I am getting old. I can’t party and stay out late and drink like I used to. I want to spend time setting up my new bedroom and actually focusing on sleeping more.



One medium or one big wall. That’s all I am saying! Woo!

Less Twitter

More thoughtful tweets.
Less tweets.
Less time.

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1 Comment

  1. Shelby

    December 29, 2019 at 19:43

    Love you Kris. Here’s to the start of a new decade – I believe you will rock 2020!

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