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2018 Retrospective and 2019 Action Plan

It’s the end of the year and that means it’s time to dig deep and really come to terms with what you’ve done and who you are. I’m talking about looking into that self-awareness mirror and not shying away from the horror staring back at you.

Or, you know, just doing a check-in to see how your year went and then having some chocolate because you’re an adult and you deserve it.

Here’s my 2018 retrospective, a great idea that I stole from my friend Nate.

I usually keep these retrospectives to myself, but am posting it here this year so I can actually follow up on it. I did that in 2016 and hit a whole bunch of great goals in 2017.

So this year I’m taking it public and holding myself accountable to the masses (or rather the great void that is the internet).

What’s a retrospective?

You may be wondering, silently to yourself. What’s that even mean?A retrospective is a list of questions that help you think through what’s happened.

At work we use them for projects and as bi-weekly checkins. The goal is to think through:

What went well

This was a year of firsts for me in a lot of different ways. That made the year exciting and really, really emotional for me. I always work through tough situations and bounce back—pretty much like a phoenix rising from the ashes and all that.

The tricky part is that I tend to break down before the whole “rising” part happens.

I cried a lot this year. I raged a lot. I worried over things that weren’t actually problems and also managed to make myself sick from the amount of stress that I basically refused to deal with.

But enough about that. What section of the post is this? Oh yeah, what went well. Alright, we’re out of that detour and back on track.

My career took off and I feel more confident than ever

This year I got so much more confident and started moving forward with my career in a targeted and meaningful way. For the past few years, I’ve wanted to be at the intersection of product, research, and design. And this year I started working at a company where I do just that.

I faced my fear and left a company where I was making a decent salary and doing work I enjoyed but where company problems weren’t being addressed. I knew from experience where these problems would lead, and also knew that I had to be honest with myself about whether or not I could handle that emotional load.

It was scary and sad to leave, but I learned three of the biggest professional lessons of my life:

If you see a problem, talk about it and try to fix it. Even if it’s scary. Even if you’re not sure you have the best solution. If something is wrong and if people aren’t being treated correctly, you have to say something. If you don’t feel safe enough to do that, then it’s time to warm up that good old network and find a new job. Because you don’t deserve the stress and they don’t deserve you.

If you’ve changed everything that’s in your power to change and you’re still unhappy, you’ve got to muster up the courage to leave. You aren’t doing yourself, your team, or the company any good by staying and being miserable. Every relationship comes to an end in one way or another, and that includes the relationship you have with your company.

Set clear boundaries and stick to them. Set meeting times that work for you. Block out days to get actual work done. Take care of your whole self. I’m pretty good at this in my personal life, but professionally it’s always been very hard for me to do. This year I learned to say “no” and actually mean it.

Once I left, I freelanced for a few months and happily found that this time around I was in demand. I actually had to decline some contracts because I had too many. That was a new feeling and I feel so lucky to have progressed to this point.

Recently I started working at small startup—a company called Gatsby. I’m finally doing the dream job that I knew had to exist somewhere. I’m right at the intersection of product, design, and research. And on top of that, I get to work with an amazing team of people.

I also worked on and learned a lot of great things this year:

I set aside dedicated time to be creative and learn

I made a goal this year when we moved back to Portland that I was going to start working with my hands more.

I used to be actively creative and would paint, throw pottery, write—you name it. Over the past 3 years I’ve been really focusing on my career. When I wasn’t on the computer working I was reading about product design, psychology, research, data infrastructure, and creating strong teams.

So this year I started taking a ceramics course. I now have some pretty badly glazed ceramic bowls and a few hours each week where I have no phone, no computer, and I just get to work with my hands.

It was honestly one of the best decisions I made this year.

Small blue cup I made that is holding several stickers

This little tea cup ended up being a sticker holder instead.

I also learned to do other creative stuff like

I’m getting involved with the people around me and making friends

We moved back to Portland this year from Austin and it was a wonderful move. I miss my friends in Austin but my quality of life is much higher here.

Now that we’ve moved back, I’ve started reaching out to the design, product management, and developer communities here to start making new friends.

We also had old friends from when we lived here before, and our families are close, so I’ve gotten to host lots of dinner parties and force my food and baked goods upon people.

And a new thing I did to participate was actually get out and vote locally. I event contacted the senator’s office and mayor’s office—advocating for smarter urban development and mobility.

I made a lot of adult decisions that have been really scary and fun

In addition to switching jobs, Jason (my partner) and I also bought our first house. It was an emotional rollercoaster, but I’m happy that we made the leap.

Jason standing in front of a Christmas tree holding several presents and smiling

This is Jason. He’s very excited about the first Christmas in the house. And his presents. And the food we’re about to eat. He’s generally pretty excited about whatever is happening next.

I love the neighborhood and am having fun attempting to learn and understand interior design. (Hint: I have no idea what I’m doing, and I’m afraid it shows.)

We’ve got plans for the kitchen, the living room, and the yard. So just you wait, in five or maybe ten years it’ll be all done and amazing!

What are my biggest opportunities for growth?

2018 was pretty good, but I have some things I’d like to improve and be more consistent with in 2019.

My overall goal for this year do more work in public. I spend a lot of time rationalizing why no one will care about the thing I want to say. But this year I’m going to work in public as a way to hold myself accountable and hopefully help people who may have similar questions.

Write in public

This year I want to start writing more publicly to think through some of my own ideas.

I’ve done a lot of work with data, testing, research, product management, organizational design, and recruitment. It’s given me the ability think cross-functionally and see second and third order effects a bit better as I’ve gotten more experience.

Every decision we make has a consequence (first order effect). But from that outcome you get additional consequences, which are the second and third order effects. Learning to think through this is helpful when thinking about product, company strategy, and organizational design.

And I think writing and posting in public will force me to work through my ideas, defend them, and hopefully help people along the way.

Reach out to more people to create a stronger community

I think I did okay reaching out to people and starting a community. I’d like to make some more close friends, which I know requires putting myself out there and meeting people.

I’d also like to get more involved in urban mobility in a more impactful way. I’ve applied to volunteer with Hack Oregon this year, a group that works to get data out into the public, and transparency is a huge part of making sure people can make informed decisions. If I get involved with that, I’ll be able to help push forward smart growth initiatives for the city.

Find additional outlets for creativity

I love gardening so would like to dedicate some time to improving my garden this year, even if I can’t make all the changes all at once. I like gardens that are magical and enchanting… so there are going to be a lot of new plants in that yard.

I’ve also never lived in a house where I could change anything, so I’m going to focus on creating a more welcoming and comfortable space throughout the whole house. And let’s hope I don’t try to paint anything. I don’t see that ending well.

How can I fix what’s not working for a better result?

This year I’m doing something a bit different to fix what’s not working. Instead of writing this and then just going on my merry way (what I did in 2016 and in 2017), I’m actually going to check in on this again at the beginning of April.

The goal is that this will keep me on track and actively trying to do better.

So this year I’m going to:

By April I should have:

Once I do the check-in, I’m going to do another retro and re-evaluate what I’ve done, what could’ve gone better, and see what goals make it to the next quarter.

That feels like an actionable plan to get me moving. What do you want to do in 2019?


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