To Whom it May Concern,

Leah Haile
Segment Design + Research
4 min readNov 8, 2021

No matter where you’re at in your career, you’ve probably been asked to set some professional goals. How many times have you set a goal for yourself only to keep pushing out the deadline because you haven’t made time for it yet? After years of trying (and failing) to achieve my goal of leaning more into coding to expand my design skillset, I finally realized that I was never going to finish that Code Academy course, because I had no passion for coding. In fact, one of the reasons I became a Design Manager is because I realized that I got way more energy from coaching other designers than designing products myself.

Setting the right goals

When I joined the Segment Design team this year, two of the designers on our Core team asked for help in setting their goals. In the short-term, they each had a good list of specific, measurable goals, but how those goals connected to their long-term vision was still a little fuzzy.

Setting goals is one of the best things you can do to create long-term vision and short-term motivation when it comes to work, but it’s important to have a connection with how they relate to your interests. If your goals and passions aren’t aligned, you’re going to struggle to make them a priority.

In order to make sure they were chasing the “right” goals, I encouraged them to step back and start by writing a letter of recommendation for their future selves.

Toot your own (future) horn

The goal of writing yourself a letter of recommendation isn’t to figure out exactly what you need to do to get a specific job at a specific company, but more to understand what qualities and skills really matter to you when it comes to your work life. Once you have a clear picture of the type of teammate you want to be, it’s much easier to work backwards into the goals you need to set in order to get there, or to map your current goals to that picture.

The idea is to write a letter that is fully aspirational; imagine that it’s your closest coworker, giving a testimony to the work you’ve done together and the reasons why you’re such a valuable member of any team. If the thought of bragging about yourself makes you feel uncomfortable, then this is the perfect activity for you! You don’t have to have already accomplished anything, you just need to describe the value that you hope to bring to the table at this current phase of your career.

Self, Meet Future Self

When we regrouped to read through their letters for their future selves, both designers were surprised at some of the differences between the goals they had started to set and the person they had described in their letters. While one designer had a list of more tactical, craft and analytics based goals, her letter was centered on her ability to guide others through ambiguity and drive strategy. For the other designer, her letter gave her more clarity on how she wants to show up for her team and where to more specifically focus her technical development as a designer. Since then, we’ve been building out career plans and goals that feel authentic and aligned to where they want to go. Don’t believe me? Check out what they had to say about it:

“I’ve written a ton of recommendations for other people but when I was asked to write my own, it really gave me an opportunity to think about what motivates me to do my best work and how I want my team to view me as a colleague. I was also able to identify areas for growth and brainstormed actionable steps with my manager to reach those goals!”

“Writing a letter of recommendation for myself required me to think about the areas of design I gravitate towards the most, and what I want to be known for as a designer. I hadn’t had a ton of constructive conversations about my career in the past, nor was I super confident on any short-term goals (despite having been working for ~5 years), so this really helped drive clarity on both of those things. It allowed me to form a more concrete vision of my future self, which then enabled me (with the help of my manager) to identify what I should work on or seek out that would help me make that vision a reality.”

Sincerely, Me

I love this exercise because you’re focusing in on who you want to be, instead of what you want to do. Once you know who you want to become, it’s much easier to set the right goals and as a bonus, you can also use feedback from your team to assess how close you’re getting to that vision of your future self. Even if you feel like you have a pretty good sense of where you’re taking your career, writing yourself a letter of recommendation is a good way to gut check how you’re progressing on the hard and soft skills that it takes to feel fulfilled at work. If you like the idea of approaching your career development from this direction, you should join us! We’re hiring great designers and I’d love to see what you write.

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