annual review - 2018



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To close 2018, I sat down and completed Rohan Rajiv’s 10 Question Annual Review. I had read annual reviews for years - and despite several attempts, had never found a format I liked before.

Rajiv’s 10 question format strikes a nice balance:

  • structured without being overly prescriptive
  • short enough to not be overwhelming
  • long enough and probing enough to provide value in the introspection and reflection it requires

Sharing this is awkward. The good feels like bragging. The bad feels like I’m seeking sympathy. The truth is that every journey is unique and I’m sharing this because I believe deeply in learning in public.

Part I – Look back

  1. Peak Moments 1a. What was the theme or peak moment of the year? (One word or line description)

    • 2018 was the year of the jump — jumping from a career I’d started into something new and unknown
    • 2019 will be the year of the landing - finding my identity as an engineer

    1b. Were there runner up theme or peak moment(s)?

    • 2018 was also the year of getting comfortable with who I am
    • 2019 will also be the year of expanding my definition of myself
  2. What were my three greatest successes / memories from the year?

    1. Graduating from Hack Reactor as class president (and Kate from Medical school!)
    2. Fulfilling a childhood dream of going to SE Asia
    3. Made new friends - neighbors, classmates, traveling peers - a lot of new, friendly faces in our life
  3. What were my three biggest lessons learned from the year?

    1. I am able to focus longer and harder on things than I ever suspected
    2. Stories we tell ourselves are powerful and can affect whether or not we accomplish our goals
    3. Fighting my strengths — There are some things I’m better at, but they don’t always align with what I want to do. The tension between them have meant I don’t end up always doing what I’m suited for, or being very happy while I’m doing what I’m good at
  4. How did the year fit into the big picture or contribute to the dreams in my life?

    • This was probably the thing I’m most proud of. 2018 was a continuation of some of the major changes I made in 2017 - i.e. starting a family with Kate as we enjoyed our first anniversary, went on an adventure to the other side of the world, and generally just supported one another. Me while Kate finished Medical school and began residency. Kate while I quit a well paying job to go to school. The school was also the first, major step I’ve taken toward a career in tech that I’ve talked about for years and hadn’t moved forward on. I remember when I started Signature and I was traveling to Nashville - one night I’m walking through downtown talking to Sam about how to get into Tech and he acknowledged that it’s pretty tough to do from the business side. So, a few years later I’m not not trying to just go to a tech company in marketing and shift - but start directly as an engineer. This has been a change that’s been several years in the making, and which took me a while to realize. It’s also the result of some of the things I’ve been working on - like who I am is why I was successful at Hack Reactor - and had I tried doing the program several years ago, there’s a good chance I wouldn’t have been successful

Part II – Look forward

  1. What are three themes I am thinking about for the coming year? Are there any “process goals” to which I want to commit?

    1. Growth - I will not be the same person at the end of 2019 that I am when I start it. I want the change to be positive
    2. Ship - Projects should not be taken on lightly - instead, I should focus on finishing what I start. If I choose not to pursue the project to the end, I should cut bait quickly and move on
    3. Let my name ring out - I do not like to self-promote, but I want 2019 to be a year when I get my name out there — by being who I am. Sharing what I learn and talking to others. It’s not about attracting undue attention, but trying to provide value by sharing my experiences
  2. What skills do I want to develop in the coming year? What actions will I take to develop them?

    1. Communication - oral and written
      • Speaking opportunities - by getting involved in meetups around town, I’ll have a chance to speak. I’ll submit RFPs to conferences when they are looking for speakers
      • Writing - by chronicling my experience on my blog, I’ll refine my writing to get to the point in a way that resonates. I’ll experiment with format and look at the results to try to see if there’s methods of writing that are more compelling
    2. Engineering
      • I’ll get a job as an engineer and not be satisfied to simply perform the duties, but look for any opportunities to learn
      • I’ll participate in the tech community here in Chicago through meetups and events to meet other engineers and work on projects
      • I’ll complete at least one course per quarter and/or read a book
    3. Basketball / Fitness
      • By maintaining a membership at EBC and attending at least one class per week and open gym at least once per week
  3. Who / what were my biggest sources of inspiration, learning, and energy this past year? Are they high on my priority list to engage with (if people) or do (if actions) in the coming year?

    1. Benjamin Graham’s The Intelligent Investor
    2. Ben Thompson & James Allworth Stratechery & The Exponent
    3. &
    4. Basketball

    A book that solidified my impression of appropriate investment strategies for me given that I do not have the time/attention to dedicate to investments. I took the advice and wrote out an investment contract that I try to remember and return to whenever I feel the need to deviate from our plan. I’m a big fan of setting up simple guardrails on behavior to make behavior easier. Eliminating the need to make the decision in the moment / expend effort.

    Q2 of 2018 I listened to every episode of Ben Thompson and James Allworth’s The Exponent. One of their final episodes prior to a hiatus was about business school and what it was like for them. While both of them were speaking from the perspective of MBAs, I took from it the lesson that understanding why you were pursuing something was far more valuable. Ben was ruthless in only accepting opportunities that would further his goal of getting into tech. A few months later I would build up the courage to do that too. and are two podcasts that I found this year which changed the way I think about coding and engineering. They’ve offered me a community that is focused on learning and growth - and almost as importantly - open to newcomers. These two podcasts opened a ton of doors through which I could walk through.

    Joining the EBC at Drew’s recommendation this fall was fantastic, because I was able to get back into playing basketball. What I love about that is that I’m moving, but it’s also an opportunity to practice a skill in a methodical way. While I’m not the best basketball player, I know the different things that make for a good basketball player. So, by playing I’m able to practice and the progress is readily visible.

  4. Who were my personal or professional board of directors, advisors, or sponsors this year? How do I plan to engage with them in the coming year?

    1. Sam - Without Sam there’s no way that I would be preparing to start a new career as an Engineer. He’s been my first call throughout the year. I’d like to rely on him less for motivation in 2019, but I would like a regular cadence of checking in on bigger projects and how to continue to direct my efforts.
    2. Andrew - With his move to Boston, I saw less of Andrew this year than I would have liked and 2019 likely won’t change that much. But, we talked a bit more about the possibility that we would go into business together. It’s a dream at the moment, but one I think we would both pursue readily given the opportunity. In 2019 I’d like to spend more time thinking about what that could look like and keeping an eye open for opportunities.
    3. Kate - Kate’s my biggest cheerleader and I am so lucky to have her encouragement. When she says she believes I can do something, it’s like a grant to go out and do it. I feel like I have super powers when she stands behind me.
  5. What do I have planned for the coming year to prioritize rest and renewal (e.g., holidays, leisure activities, hobbies, etc.)?

    1. Big ticket items
      1. Trips to Mexico City & Hawaii early in the year
      2. Meditation retreat - A 10 day retreat in 2019
      3. Trip with Zimmy and Ari
    2. Habits
      1. Basketball and workout classes
      2. Reading long form
  6. What are my three most important core beliefs or principles? Are my goals for the coming year aligned with these core beliefs?

    1. Attention - Do one thing at a time
    2. Adaptability - No strategy is perfect in every situation. Adjust accordingly.
    3. Honesty - I’m not going to be perfect, but being able to be honest about that, to myself, to Kate, to everyone else, is important. If I don’t meditate everyday, acknowledge that. If I don’t write every day, recognize that that’s okay. If I fail, honor that failure by recognizing it and learning from it.
    4. Balance - Whether that means balancing what I’m learning so that I’m exposed to many things or how I’m learning (scribing and conjuring), or just avoiding burn out by being sure to refresh myself.

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  • Hi there and thanks for reading! My name's Stephen. I live in Chicago with my wife, Kate, and dog, Finn. Want more? See about and get in touch!