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Have you ever wanted to do something? Perhaps go to college. Or start a blog. Or pay off debt. Or climb a mountain. Or raise children. Or create and run a school in the Philippines. Or retire near a beach. 

Have you ever made a todo list, a bucket list, new year resolutions, goal or (gasp) an objective with some key results? I’ve tried all of these, and probably more, to plan my future. My most recent iteration is:

• Write down 100 of your dreams

• Work towards and experiment on at least one dream (nearly) every day

• Curate, refine and adapt your dreams regularly

• Tell other people about your dreams

• Offer to and then help other people with their dreams

In this post, I want to share a bit about how I got to this iteration and how I want to move forward from here.

My origin story to my current life planning approach

To start, let’s rewind time. For most of my life, I don’t remember planning my future with much intention. 

The earliest I can remember somewhat seriously thinking ahead a few years was in middle school or early high school when I kiiinda thought about what I wanted to do for a career. I thought I wanted to be a lawyer because I felt like I was good at arguing. Over time in high school, I realized I didn’t want to spend my entire time arguing so that plan faded.

Later in high school, I stumbled into a Cisco networking course offered by my high school after burning out of Spanish and looking for an alternative. At this point, I had gotten pretty into computers at home: building my own, learning how to code a little bit, etc. This Cisco course sounded interesting. While taking the class, I found that the material came to me easily. I ended up taking other classes which let me use computers like software programming, web design, videography (which allowed us to edit/produce video). When choosing a college degree program, I found RIT’s Applied Networking and Systems Administration which allowed me to continue learning about Cisco networking and software programming. I think that I thought that with this degree, I could probably be useful at many different companies in many different industries – or maybe that’s a thought that came later.

In college, around 2004 or 2005, I was interested in studying a language as a vehicle to learn about other countries and cultures. Or, maybe I had some requirement to take some Liberal Arts courses. Either way, I remember deciding between Arabic or some other language. I thought that learning Arabic and computers would be a fast path to joining the US Government, perhaps the National Security Agency. While I can’t remember how I got to these two, my decision narrowed to Arabic or Italian. The story I tell myself now is that I chose Italian because I was more interested in that food culture. And, so I went on to study Italian. I loved it. My professor, Elisabetta D’Amanda, was a big reason for loving Italian – she was personal, authentic, energizing, bold, and got shit done. While most other language departments at the university sent students on study abroad through third parties, she ran a custom and very personal study abroad program herself in Italy. She sponsored the Italian culture club at our university. She hosted an Italian film festival. I followed Professor D’Amanda with zeal through many of these eye-opening experiences. I went to study abroad in Italy. I became the president of the Italian club. I supported at a few of the film festival events. At the onset, I had no idea that I’d stumble into so much happiness.

Through college, I realized I liked the system administration parts of my core studies more than the computer science or networking parts. While I did get satisfaction out of creating things and solving problems in code, it got boring. However, I really enjoyed bringing pieces together in an ever changing landscape. I figured after graduating that I’d get a job in Microsoft Windows system administration – that’s what I did for some of my internships during school. So, it was somewhat surprising to me that I applied for a junior Linux system administrator position at Indeed in their Austin office, got interviewed, got an offer and started in Nov 2008. I thought I’d go to Indeed in Austin for a few years and find another company to go work at. My good friend Scott was living in Austin at the time. Austin was closer to my mom, sister, and grandma – I had been far away for four years. The whole “move to another company in a few years” plan adapted somewhere along the way: I’m still at Indeed in Austin in 2021 – 12.5 years :P I didn’t realize I’d love the environment so much.

Mar and I met in mid-2015. Mar helped me see some of the benefits of planning: I was impressed by how much she had her shit together. I remember being in awe of her character, perseverance, independence, and accountability. Over the years, she’s imbued upon me some of her greatness. I’m so lucky to have found Mar.

Mar and I got married on March 31, 2017. In mid-2017, we found out that Mar was pregnant and penned our family values. With these values to guide our future decisions, we were starting to plan long-term on a bigger scale than we’d done before.

A few months later, in December 2017, as Leo’s March birthday neared, I wondered whether I would be able to balance my time in a way that would feel “me”. Playing off of the family values we’d made, my experiences creating teams and using OKRs at work, and my desire to practice planning, I wrote a personal mission, vision, strategy, some life goals, and some OKRs based on https://www.extension.iastate.edu/agdm/wholefarm/html/c5-09.html:

-–

Vision: A man who is healthy and helps others.

Mission: To enjoy the present, learn, and help others grow.

Strategy: Grow a family.

Strategy: Exercise.

Life goals:

• Grow a family

• Spend time with friends and family

• Climb and sleep on a big wall

• Go outside, especially to wild places

• Eat tasty food

OKRs:

I will stay strong and flexible enough to play soccer and climb without becoming injured like the knee tweaks and shoulder ligament tear which kept me away for years by

• Lifting: OTL 1x/week

• Soccer 1x/week

• ABP 2x/week

• Movement: GMB 3x/week

I will lead 5.7 trad multi pitch by

• Practice leading sport MP

• Practice leading the rappel

• Watch videos and read about hanging on trad gear

• Place trad gear at e-rock on the ground

• Hang/fall on trad gear near the ground with crash pad?

• Planning a trad MP trip

I will learn how to juggle 3 balls by 

• Practicing for 5 minutes 2x/week

• Advancing to next skill after comfort

I will determine what we’re doing about taxes by

• Learn about joint-filing benefits

-–

I tried that approach to practice what I was starting to see more of at work – business language like vision, mission, strategy, etc. It was pretty foreign to me, and I thought it would be good to practice. I didn’t get an MBA (Mar did). But through Jeff Davis’ leadership in the Indeed SRE organization, I was getting a little more exposed to this side of business planning.

I liked the results of this planning process. It helped me articulate myself to myself.

The tax-related goal was very straightforward. I did juggle for a few handfuls of days, but that goal fizzled out.

I leaned into the climbing & fitness goals mostly. Leo was born a few months later in March 2018. During my 6-week parental leave, I spent quite a bit of time watching climbing documentaries at the hospital and going to the rock climbing gym (ABP; Austin Bouldering Project). I got pretty strong and solid on high difficulty routes during those 6 weeks. I remember remarking to my good friend Scott that I was going to miss climbing so much when I went back to work. He joked: well maybe you should retire. 

That joke piqued my curiosity: could I retire? What would that take? I started to research. I found the FIRE movement. FIRE stands for financial independence, retire early. It seemed plausible. So, I ran some numbers, started budgeting more, shifted grocery shopping from Whole Foods to HEB, and more. I’ll write other posts about my FIRE plans, but for now, I’m going to keep moving along to get to explaining my current iteration of planning.

In late 2019 or early 2020, Mar’s team at work went through an exercise where they each listed 100 dreams, and came together as a team to discuss some of each other’s dreams. The idea came from her boss’s boss who’d read it from The Dream Manager by Matthew Kelly. Mar excitedly told me about the exercise/discussion and suggested I try to list out my dreams and we could discuss. 

Here’s the list I came up with:

• read with kids every night

• live in many countries

• vacation with family 4+ times / year

• weekly date

• kids music and movement class

• kids swim class

• hike 1-2 times / mo

• cook for my family

• read a book with mar; and discuss it chapter by chapter

After making it, I felt underwhelmed by this list:

• It was way shorter than 100.

• These all seem to be things we are already doing. 

• I was pretty focused on my family. I think because Mar suggested the exercise, I was very narrowly focused on family only.

• I tried to apply some of the lessons I learned through using OKRs at work like measuring outcomes, not outputs

• Was I not more creative than this?

And, I don’t remember ever seeing Mar’s list of 100. Not a knock on Mar. I never asked. I think my “lackluster” dream list discouraged me.

Later in the year, in August 2020, I actually read – well listened to – The Dream Manager by Matthew Kelly. I had just started leading the global SRE organization at Indeed. I was gearing up to go on an alpine climbing trip for 10 days. And, I remember taking Leo to the school playground in his red Cozy Coupe, and finishing The Dream Manager audiobook on Audible.

I was in the middle of the school field thinking: Oh, the 100 dreams is to bust you out of worrying about the quality and characteristics of each individual dream. It’s ok if some dreams are short term, some are long-term, some are about a personal adventure goal, some are results, some are outputs. 

I wrote down 60 dreams that day. Some of them were from that earlier list. Some were from another list of activities that Mar and I had been storing in a Google Sheet.

I planned to reflect on the dreams, and possibly think of new ones, on my late August climbing trip. What else would I do for the hours of hiking, belaying, flying, and generally waiting to do the next thing on a climbing trip? Well, it turns out that even when I’m belaying my partner for an hour or more, I’m not really able to think about my long-term goals. Maybe there’s something about being strapped to the side of a cliff with a few pieces of climbing gear that keeps my mind generally focused on climbing, or I’m blank & resting.

When I returned from the trip, I added a few more dreams, including some work dreams.

In November, I remember being in a meeting with Jeff Davis where he was talking to customer teams within Indeed. At around this time, my ears were also open to ways to improve collaboration – both because of engagement survey results within Indeed, and because I’d been working on Indeed’s migration to AWS which was a huge effort and I wanted to be better at working with people across the organization. Jeff’s approach to the meeting was so simple yet effective:

• Here’s who we are

• Here’s what we are thinking about working on

• What are you thinking about working on

• Oh these are places we can probably work together

So, when 2021 was starting to near, with Mar and I expecting our second son in a few months, we got to our dream lists again.

This time, with my energy after reading The Dream Manager and seeing Jeff facilitate that meeting, Mar and I added more to our dream lists. Mar read my dreams. I read her dreams. We made shared dreams.

She learned more about me, and I learned more about her. Just like those customer meetings at work. We understood each other better, could support each other, and could share goals.

We can be supported if we share our goals and challenges with others. If we don’t tell others about our needs and desires, they probably won’t know and you probably won’t get help. You won’t need help for everything you want to do. And, you probably won’t want help for everything you want to do.

This is so simple that it feels silly writing so many words to explain it. 

But, writing words is one of the reasons I made this blog (see Welcome). And, sharing my thoughts even when it feels silly is one of the things I want to do more of.

So, let’s dive into each of the aspects of my current iteration of life planning :)

Write down 100 of your dreams

A dream in this sense is simply something you want to do.

A key point here is to unleash your creativity. Don’t worry about:

• Well formed dreams

• What % of the dreams are for yourself, vs your family, vs your values

• Any guidelines from your goal setting at work (e.g. outcomes over outputs)

• Achievability

• Timeline - e.g. this week, next month, 3 years, lifetime

It took me a few passes to get 100 in my list. Don’t worry about getting to 100 in the first pass. I like this size of a list because it gives me plenty of room to stretch into areas of intense existing interest like climbing and new-to-me areas like charitable donations and painting.

I put them in a Google sheet so I could add columns of metadata if I wanted (e.g. like whether the dream matched a value of mine, whether I share the dream with Mar, etc). Though, as I start to play around with Roam Research, I’ve been considering moving the Dreams there if Roam sticks.

Work towards and experiment on at least one dream (nearly) every day

It’s obvious that you cannot work on 100 dreams simultaneously. And, it’s unreasonable to hold yourself to perfection that you MUST advance a dream every day.

Change is hard. There are plenty of resources about why New Year’s resolutions don’t happen, why companies go out of business, etc. We have limited time and money, and we also have to stay healthy. (See Risk Modeling in a Dynamic Society: A Modeling Problem by Jens Rasmussen for an elaboration which I seem to be using as a hammer these days since it feels so applicable in personal and work life).

And, also: change is constant. New possibilities pop up all the time, pulling your energy in different directions. Surprises happen (COVID, the Uri storm, etc) that shock our way of life, not to mention stall our ambitious dreams. COVID majorly disrupted my normal workout and fitness regimen.

So, with those “Don’t be too hard on yourself” disclaimers out of the way: what’s the point of having dreams if you don’t work towards them?

I try to do SOMETHING towards my dreams every day:

• Work on an existing dream

• Practice

• Experiment

• Plan

• Reflect

• Write

• Collaborate

• Get assistance

• etc

• Curate dreams (see next section)

I’ve been using a Habit tracker on my phone (https://play.google.com/store/apps/details?id=org.isoron.uhabits&hl=en_US&gl=US) for a few years to help me remember to do things like meditate, practice Spanish, etc. This has been a helpful way to remind myself what I want to do with my time. As I’m working on a new dream, sometimes I make it a habit in my tracker. Over time, some become so set in my life that I don’t need a habit in the tracker.

https://hiddenbrain.org/podcast/creatures-of-habit/ is a recent podcast that talks about habit research and how you can work on your own habits.

Curate, refine and adapt your dreams regularly

Look at, revise, elaborate, etc your dreams as often as sustainably possible. I started with a daily review of the 100, but that quickly fizzled out :). At this point, I’m doing dream curation roughly weekly, and using the Habit tracker for daily/weekly progress towards a few different dreams (e.g. learning Spanish). Yes, I have a habit in the tracker for “Dream curation”. 

The reasons for dream curation are to make habits of

• Reviewing & celebrating recent accomplishments & progress

• Finding a step forward on at least one dream, if not more

• Editing, reprioritizing, adding, removing dreams

Tell other people about your dreams

I think sharing your dreams has many benefits:

• You make yourself seen. Your family, friends, and others get to know you better.

• You practice vulnerability.

• Others may help in various ways

• Simple “you got this” affirmations

• Point you to people in their network who may be able to help

• Share knowledge or references

• Challenge your dreams and perspective, helping you articulate or adapt your dreams

• Spend their time and/or money on your dreams

• Include you in their life in new ways

• It gives you an opportunity to ask them about their dreams

• Others may share their dreams with you.

Offer to and then help other people with their dreams

We’re better together. Groups of people band together to pool expertise, resources, attention, etc to accomplish a shared goal. There are teams, organizations, communities, companies, etc. 

I’d like to create a Dream Team: a group of people who help each other achieve their dreams.

What are your spouse’s dreams?

What are your parent’s dreams? 

What are your sibling’s dreams?

What are your friend’s dreams?

What are your colleague’s dreams?

Do they know your dreams?

Imagine how much more you’d learn about the people you love and support.

Imagine how much we could help each other, if we talked about our dreams.

I think by talking about our dreams, and helping others with their dreams, we create a virtuous feedback cycle. I feel good about helping you with your dream. You reciprocate. I reciprocate. Etc.

I’m just dipping my toes into all of this. I’m sure I’ll learn a lot along the way :)

My dreams

This is a snapshot of my current dreams. I’ll need to determine how, if at all, I want to update the list over time. It’s not sorted, though in some spots, it’s loosely grouped.

• no alcohol for 9 months

• meditate every day for 1 month

• whole30

• go 1 day a week with < 10 minutes of phone screen time, for a month

• date night monthly

• start listening to new music again

• write reverse bucket list

• bird watch with leo

• start bird watching again

• Little library

• climb 3+ days a week, for a month

• live in costa rica

• write a blog for a year (Hi, you’re reading this on my blog)

• FIRE before 41

• Reverse rollover Mar’s deductible tIRA 

• follow climbing fitness program for 3 months

• workout 3+ days a week, for a month

• help mom retire

• read > 75% non-work (other non-fiction, fiction, family, adventure)

• read < 25% work

• 2 hours per day for growth: spanish, learning (read or listen), writing

• 2 hours per day for well-being: meditate, dreams, workout, gratitude journal

• cook 4 times per week

• give to charity

• add more dreams with leo and nico

• get better at asking questions like a journalist or psychologist

• get a tattoo with at least one of mar, leo, or nico

• live in spain

• meditate for 1 hour

• make sauerkraut

• make almond milk

• donate $1000 to a single charity

• read a book with mar; and discuss it chapter by chapter

• no alcohol for November, 5 years in a row

• climb epinephrine

• growth: teaching as a habit

• make yogurt

• listen to an entire Mars Volta album with Mar, and talk about it

• donate $10000 to charity in 1 year

• learn an instrument

• write a poem

• grow food

• learn a card trick

• learn a coin trick

• learn to sew basic patches

• learn to dance: salsa

• learn to dance: tango

• learn to swim; do laps for 1 mile

• have a visible six pack

• volunteer for a social justice effort

• Volunteer or work for Electronic Frontier Foundation

• invent something physical and then sell it

• spend an entire day painting

• marathon

• learn to surf

• get a sleeve tattoo (mountain, climbing, growth/wellbeing)

• hike Appalachian trail with mom

• Start a school in the Philippines

• sleep on a portaledge to complete a climb

• coach Leo’s team sport

• hike Crested Butte to aspen

• trek in europe over a 1 month period

• trek in himalayas (inspired by Urge to Know)

• trek the O in patagonia (O = W + more)

• extended vacation to thailand (vacation or live?)

• extended vacation to vietnam (vacation or live?)

• road trip: asia

• road trip: europe

• road trip: south america

• road trip: USA

• stay at a castle

• stay at a ice hotel

• vacation africa

• vacation germany

• vacation in Mexico City

• vacation in Oaxaca

• vacation to australia

• vacation to colombia (minca, ciudad perdida)

• Growth: teaching as a habit

• vacation to new zealand

• vacation to panama (la loma mountain lodge per dr dave)

• vacation with koppes + donas out of the country

• go to earth’s moon

• go to mars

• go to outer space

• live in brazil

• live in colorado

• party at the top of circuit of the americas (COTA)

• party with a kennedy

• party at the world’s top 10 parties

• perform in a play or musical as an adult

• learn portuguese

• climb el capitan

• climb half dome

• climb in asia

• climb in europe

• climb in indian creek

• own a home away from a big city

• go 1 month without internet

• sell a painting

• triathlon

• be in ocean water every day for 1 month

• Work on race equality

• Work on gender equality

• Work on global warming (e.g. Net-zero America policy and/or execution)

• Work: Get more former SysApp promoted

• Work: Meet SLOs during failure testing

• Work: SRE & SWE have same access

• Work: Product teams operate their services incl 24x7 on-call

• Work: Report on website SLOs + EVNTs to GMs

• Work: Share EVNT story of the month

• Work: Increase gender diversity in SRE

• Work: Performance and failure testing in release pipelines

• Work: Scale SRE sub-linearly

On planning

Life is complex. There are always many variables. No design or plan is ever perfect. When you get to work, when the “rubber meets the road”, when you’re “operating the system”, you’ll undoubtedly adjust along the way. 

As Tim Harford nicely illustrated in Adapt that success requires failure:

• Try new things, with the expectation that some will fail (variation)

• Make failure survivable, because failure will happen a lot (survivability)

• Know when you fail (selection)

(The book draws from ideas Harford dubs “Palchinsky’s principles”, Natural selection, and spends most of the time going through a variety of stories to support the central thesis).

All of life (and successes from living beings like families, packs, teams, organizations, companies, etc) follow this process of evolution through variation, survivability and selection. 

All life is this continuous process of learning and adapting. Developing and leaning into a growth mindset may be a key to happiness and success. Balancing growth and wellbeing is vital for longevity – we can do so much, but we do have limits :)

Follow up

Reach out if you want to chat about any of this. I’d love to chat more and have you join a Dream Team with me :)

If you don’t know how to get in touch, you can find multiple ways to contact me at https://www.jasonkoppe.com/

This post is quite long, and there are many other topics I want to write about as follow ups here, including, but not limited to:

• You are enough. You don’t have to prove yourself by accomplishing more and more and more and more.

• You have done a lot! Recognize that! Consider a reverse bucket list :)

• Offering list - what I can offer others. what others can offer me. (inspired from Shani Graham’s TEDxPerth talk)

• Burnout

• Defining fears (e.g. Tim Ferriss TED2017 talk) 

• Core values & family values

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