A Designer’s Semi-mid-life Crisis

Jacalin Ding
7 min readFeb 15, 2024

You don’t work for the job. The job is just a token to help you get to where your goal is.

TLDR:

  • The big mistake designers often make in their career is choosing jobs based on available opportunities rather than their personal goals.
  • Personal journey on the mistakes I’ve made through out Junior, Mid, Senior stages of my design career.
  • Reflection on what I would have done differently.
  • Finally I shared my value and goal evaluation framework to help guild you how to align your values to job opportunities.

Meet Jane, she’s in her second year of her design career. One day, she reached out to me seeking mentorship on navigating her next career move. Jane had been pondering which company to join next. Apparently, three scale-up companies’ HR departments had already reached out to her, indicating these opportunities were likely to progress to the interview stage. Jane wanted my guidance in selecting the best option.

I prompted Jane to envision her future: What does success look like in her world? What would truly make her happy and proud?

“Mmm…,” Jane mused, glancing to the corner of the room, trying to gather her thoughts. A few minutes later, she gave me a generic response:

“I want to be a senior designer at a well-known company. It would look good on my resume.”

I appreciated Jane’s honesty. It was a good starting point.

But I couldn’t help but wonder: Is that all? Is working at a big company with a fancy title enough to justify spending eight hours a day, five days a week of your time?

Jane isn’t alone. Over the years, I’ve encountered many designers who switch roles only to find themselves selecting from the companies readily available to them.

There are numerous questions designers should ask themselves before settling on a company simply because it wants them.

The truth is, I’ve been in Jane’s shoes many times. As I’ve progressed through 15 years in the design field, my values and motivations have continued to shift. Looking back, I could have said no to about 50% of the jobs I’ve taken.

Here’s my personal journey:

🌈

Early stage: “I just want a job. Any job.”

I was young and naive, embracing the “girls just wanna have fun” vibe.

“If a company wants to hire me, let’s do it.”

If companies came knocking, they were the ones I’d consider first. It was easier, required less effort. That feeling of ‘being wanted,’ or whatever fed my ego, I’d take it. But I had a lot of fun! My skills were all over the place — building websites, branding design, graphic design, window displays… you name it.

There was no focus, I didn’t know the need to find my design specialty. While I had the chance to dip my feet into different waters to try things out, my skills were scattered.

🏋🏻‍♂️

Mid-stage: “I want a job at cool, big-name companies.”

Once I had some experience under my belt, I aimed to work with cool, big-name companies/brands. That would look good on my CV.

I didn’t consider whether these companies contributed to the greater good of humanity. I took projects from the likes of Coca-Cola, M&Ms, Kellogg’s, and others. These companies had ample budgets for ambitious campaigns. I traveled around the world and worked, wanting my work to be publicly visible.

Shamelessly, at one point, I even contributed to a tobacco brand’s project. Twelve years later, I still feel terrible knowing my time and energy contributed to what I called “Sell fat kids with fat food” capitalism. That phase lasted four years.

👩🏼‍💻

Senior: I want a job that’s ‘hot’ or about to take off!

I started to march into product design and was obsessed.

Many opportunities came to me organically. I transitioned from one job to another without breaks. I had the chance to work with incredible people who were building what the future could look like. I’m talking about AR innovations in 2012 when few in Australia could even define ‘AR.’

I then worked for startups trying to tackle the next big thing (but often lacking the leadership quality or market fit to scale those companies). Those were undoubtedly some of the most exciting work I’ve done. It felt like riding roller coasters every day, you never know what’s coming. My skills were growing rapidly.

But, of course, there’s a ‘but’:

I was working 10–12 hours a day, most days. I was ALL IN!

When my niece was born, instead of spending valuable evenings with her, I was burning the midnight oil creating some ‘hip’ AR projects or hustling for tech startups I didn’t really care about anymore. I did this for five years, on and off.

💣 This is the truth bomb:

The only people in the world who remember that I’ve always worked late and being stressed are my loving partner and my family. 🥹

It was a wake-up call for me.

I decided to take a sabbatical, traveled for 2 months, and took 7 months off to focus entirely on what I want and need. (I wrote about that mental health break here). I returned with clarity, and took my time to vet companies carefully. Proud to announce I’m now at a position where I can spread my wings to make positive impacts, while having the quality of life balance I need.

So, the million-dollar question is:

If I could go back in time, what would I have done differently?

Denzel Washington once said at a university commencement speech

“You pray for rain, you gotta deal with the mud too. That’s a part of it.”

Well said. Without those experiences, I wouldn’t understand the consequences of those decisions I’ve made. I wish I had made a conscious effort to reflect on my values for work and in life more often.

I’ve taken the stairs, and I hope sharing these experiences can help others take the lift.

Here’s what I would have done differently:

Take time off between jobs to evaluable these questions:

  • What problem in the world am I passionate about contributing to?
  • Will my work benefit the greater good of humanity?
  • Who do I see myself learning from?

Follow these steps of self evaluation:

1 — Visualize what future success looks like — the North Star.

Write it down. I repeat: WRITE IT DOWN. Imagine you’re drafting a press release article about that future, describing the environment, feelings, and activities in as much detail as possible. Whatever you do at that point, it must be something you’re absolutely passionate about (e.g., a sold-out speaking gig at SXSW about ethics in the design industry).

2-List the skills ‘future you’ will need to reach that success state.

If becoming that speaker at SXSW is the dream, the required skills might include storytelling, public speaking, confidence, domain expertise, etc. Be detailed.

3. Honestly evaluate where you are today — strengths, weaknesses, and skills.

I would also seek input from people I trust to build this list. Next to that list, add the improvements needed to march towards your North Star. Then reach out to opportunities to work on those skills. (eg. If you haven’t tapped into speaking opportunities yet, discuss this with your manager and seek support to create the necessary environment.) Just remember: In life, you don’t get what you deserve; you get what you ask for.

4. Continuously self-evaluate that list from step 3 and build on it.

5. Rinse and repeat: Refine the North Star story and take steps 3–4.

👆🏼 This is precisely the method I teach my students in my course.

Following these steps can help you avoid time-wasting traps that don’t align with your goals and values. Don’t forget to have fun. The people/teams you work with along this journey would be the most important decision-makers for you — make sure you include these in your vetting criteria.

I also wrote an article here about “how to vet companies before you join”. This might help some of you make decisions.

The average person will spend 90,000 hours at work over a lifetime. That’s one-third of our lifetime. Time is your most valuable asset. Use it wisely. Spend it with people who can help you grow.

If you’re interested in learning more, give this article a clap 👏🏼 drop me a message on LinkedIn or sign up on my website. I also run a monthly exclusive group mentor session with my email list where you get to ask anything.

A video and action worksheet for personal value evaluation framework will be shared when they’re ready.

til next time.
Take care.

Jac x

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