Five Challenges to Prepare for a Values-Based Job Search

Craft your ideal role to find a job you love

Taylor Simpson
Apr 25 · 6 min read
Illustration by Taylor Simpson

If you’re like me, doing work you love is everything. The thought of trudging through a 9–5 I hate makes me cringe.

When I was laid off, I thought finding a new job would be easy, but I was way wrong. Okay, it could’ve been easy, but I decided to face uncertainty while unemployed and further define my values. I didn’t want to jump into the next job that came my way; I wanted to find a job that matched what I wanted for my future.

I had to do some digging to discover what I wanted, which I’ve laid out in these challenges. They’ll help you reflect on your experiences, define your ideal company specs, craft an ideal role that uses your strengths and challenges you to grow, and create a statement to kickstart your job search.

Challenge One: Reflection

Reflect on at least three of your past job experiences. It can even be an unrelated job title or one you held in high school if you don’t have much experience in your field yet, and list out three things for each:

  1. What did you like about it?
  2. What did you not like?
  3. What was missing?

Bonus: Articulate why.

If you’re feeling stuck, review challenge two for more ideas to reflect on.

Each realization in my previous jobs informed what I wanted in the next, where I would inevitably come to another realization. In a way, I treated each new role as an experiment to test my new hypotheses.

  • My first internship taught me that a super-small design agency was a recipe for stress, but I liked New York and being able to bike to work. My second internship taught me I didn’t like the San Francisco tech bubble or the silos and secrecy within a super large organization.
  • In my first job out of college, I discovered I loved working in-house for startups and the value of great benefits and amazing coworkers. It was a role that gave me a lot of room to grow and get my hands dirty in a lot of areas of the business. It also taught me that the marketing technology industry wasn’t my dream industry. In essence, I always felt a little morally weird about how our product eventually served capitalism for big retail companies. And after 2.5 years in New York, the city was wearing on me.
  • While unemployed, I tested out freelancing and discovered that I loved working from home and dictating my schedule, but the volatility in job security wasn’t for me.

Looking at my experiences, it became clear I should be looking for a mission-driven startup or mid-size company. It meant focusing more on industries like wellness, policy, creativity, and education. I also decided to prioritize remote-first companies or those located in Seattle, where I wanted to move.

Challenge Two: Define your ideal company

Go through each of these points and define what your ideal company looks like. What are you not willing to compromise on? Where is there wiggle room?

  • Job Type: Contract or full-time, agency or in-house, seniority level, job title
  • Industry: Tech is what we design, not the industries we serve–healthcare, policy, education, retail, marketing, productivity, social media, real estate, etc.
  • Size and Structure: Overall company, then the team you’ll be on and the teams you’ll collaborate with
  • Stage: Startup (and all the stages within that), private or IPO’d, nonprofit, industry bastion
  • Location and Space: Remote or remote-friendly, city, commute time, travel needs, office space
  • Pay and Benefits: Hourly rate or salary, equity, paid time off, parental leave, medical coverage, 401k, commute reimbursements, meals, company outings, etc.
  • Culture and Values: How they behave and work together, plus how they view the work they do

Challenge Three: Define your ideal role description

Within one job title, responsibilities and skills can vary from company to company. Knowing your ideal description can help cut the clutter in the job search process, and further knowing how it breaks down into to your unique strengths and career goals will strengthen your applications and interviews.

Look through 10 job postings’ role and responsibilities sections for this challenge. It doesn’t matter who the companies are; the goal is to get a range of descriptions. Answer these questions as you review:

  • What gets you excited? What do you recoil at?
  • What makes you nervous? Why?
  • What are your strengths? What do you need to learn?
  • What value do you want to bring to the company?

Tip: Paste specific points of the descriptions into a doc to collect your notes.

After, review what your answers say about who you are — you might learn something new–and create a shortlist of the most critical elements you’d see in your ideal job description.

I found that what made me most excited tied closely to my unique strengths. In the strength department, the biggest realization I came to is that I’m a systems thinker. Those words weren’t in any of my previous job descriptions, but I was inherently using that skill because I was driven to. Seeing that it was a real thing made me excited about postings that included it. On the other hand, we all have strengths that aren’t necessarily our version of fun. My ask of you is to follow your fun — you’ll feel more energized to do your work, do a better job, and end up more fulfilled.

Sometimes what makes you nervous is also what makes you excited, the difference being it’s what you need to improve on. For me, it’s the intricacies of leading communication and cross-functional collaboration. I believe this is the path I want to go down, rather than being siloed, but it’s also what I need to work on the most and am excited to learn. So my second ask is to go for the work that makes you nervous in that excited way — you’ll grow instead of feeling stagnant.

Remember that value works both ways. It’s not only how you contribute to the company’s success, but how the company’s culture values you and your work. I wanted to find a company that valued its employees as human beings so I could bring my authentic self to work, and like me, championed the impact of design across the org rather than viewing it as a service. The last ask, consider how you want to be valued in return for all the value you bring.

Challenge Four: List your 10 dream companies

Make a list of 10 companies you’d like to work for, regardless of whether they’re hiring or not. They should match your requirements discovered in the previous challenges.

To research a company, you can dig into their about and careers pages and read the recommended links, read employee reviews on Glassdoor highlighting the pros and cons, and see what their employees are posting on LinkedIn.

Bonus: Set up a coffee date with someone who works there. You can find out more about what it’s like to work there, and then you’ll have a connection for when they’re hiring.

Challenge Five: Share your statement

Using your learnings, craft a statement to share with your network to alert them of your search. It should succinctly combine the most crucial elements from challenges one, two, and three. You can think of it as a mini job posting.

This example is the one I used to share with my network in emails, on LinkedIn, and Instagram:

I’m looking to start a new Product Design (UI/UX) role with a mission-driven company creating for the greater good.

  • Remote, NYC, or Seattle
  • Building tech for education, policy, wellness, personal growth, creativity, productivity, and dev tools
  • 3+ yrs experience in product and visual design with startups, in-house, and agencies
  • I’m empathic, curious, and analytical–I love exploring the human condition
  • I take the initiative and keep experimenting

Please put me in touch with your team, friends, and industry connections. Thank you!

[insert contact info and portfolio link]

Notice how the statement combines my experience, preferred location, culture, industries, and work approach. I wasn’t willing to compromise on these things. When communicating with recruiters, I also found it useful to express what I was not looking for to save us both time.


I hope these challenges prove to be useful in finding a job that matches your values. If you want more challenges to define your values, check out the Full Time You workbook by Meg Lewis (aka Darn Gooood). Her challenges are what really kicked this all off for me.

The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication.

Taylor Simpson

Written by

Product designer, illustrator, creative nonfiction writer

The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here.

Taylor Simpson

Written by

Product designer, illustrator, creative nonfiction writer

The Post-Grad Survival Guide

Medium’s Millennial Work, Money and Life Advice Publication. We discuss our post-grad blues, successes, failures, and everyday life right here.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch

Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore

Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store