Seven Steps to Finding a Career That Fits

How anyone can project manage their way to a job they love

It’s like riding a bike — across a glacier.

It’s like riding a bike — across a glacier.

When people ask ‘what do you do?’ are they asking how you contribute to society, earn a living, or how you spend your days? What if the answers are radically different? You might love some aspects of your current job, but don’t see growth opportunity. You might have autonomy in your position, but don’t feel connected to the purpose. You might be casually looking for better opportunities but not sure how to evaluate options. You don’t feel fulfilled and you know there’s more out there. Maybe it’s time to take a closer look at what you’ve done so far and what’s on the horizon to feel inspired to make a leap.

When I started to think about career-switching away from architecture, the prospect seemed daunting. I had already spent seven years in the profession, and had taken seven licensure exams, on top of seven years of schooling. Instead of thinking of it as lost time, I learned to pivot. In the spirit of lucky sevens, I’ll show you the seven steps I took to bet on myself.



Step 1: Clean house.

“Be regular and orderly in your life, so that you may be violent and original in your work.” Gustave Flaubert

I did a deep clean and inventory of everything I have and have let in, digitally and physically. I’m an inbox zero person. Email is my to-do list, so I unsubscribe from anything that isn’t aligned with my goals. It’s worth the time to clean house to stay focused to really decide what is relevant and useful to you going forward. I stay on top of my calendar and protect it.

Time is your most precious resource; spend it wisely.

Striving for order within your household and holistically in your life is a high bar. I didn’t have a lot of emotional support for my journey to color outside the lines. I was told to stay in my lane, keep my head down, and persevere in the status quo. I felt selfish and arrogant to want something more. It was a tough decision to leave a comfortable life and a respectable career for something unknown and intangible. While I believe determination is a good quality that builds character, I discovered that I needed to draw my own framework and decide for myself what matters to me.

During this sabbatical, I quit my job, broke up with my boyfriend, sustained a major injury to my leg in Patagonia, and turned 32. The universe had spoken. It took awhile, but it’s important to get your personal life in order, so that you can prioritize what’s important to who you’re becoming. With this newfound awareness, I felt confident to go out and tell my story professionally.

Gmail has an unsubscribe option at the top of emails distributed on a listserve. Use it.

Marie Kondo tops into our innate desire to simplify. Follow her creed to declutter your space and your mind will follow. Letting go of your previous identity is hard. Rewrite your bio for the person you want to be known as. Find out where you’re most productive and efficient. I have 4 coffee shops in heavy rotation, where I know I can write, be comfortable, have views to the outside, and spend less than $5 on a chai latte in exchange for workspace.



Step 2: Research your end game.

“A mind stretched to a new idea never returns to its original dimension.” — Oliver Wendell Holmes

Try to simplify complex ideas. No one is just one thing.

Try to simplify complex ideas. No one is just one thing.

If you’re reading this, you likely have a feeling that what you’re doing now is not where you want to be for the rest of your career. This revelation happened for me over the course of 6 months- I attended SXSW Interactive 2018 and was overcome with emotion and energy. I knew that I wanted to be working at the forefront of technology and design. I met futurists, visionaries, and creatives who inspired me. I had found an aspirational group of people, and another industry that I could now dive head first into. If you’ve landed on a passion, it won’t feel like work- let your curiosity lead you.

What are the disciplines and terminology of the new industry? What are the overlaps between what you’re doing now and this new industry? Who do you know working in this new industry? These foundational questions helped focus my leap.

For me, the task ahead was to define “What exactly is experience design?” I tried making a diagram about all the different disciplines that blend together to make this role. I looked at what I had studied, what I did in my last few jobs, and what I love to do. If you’re a lifelong learner, this process will never end, so make sure you get good at refining how you talk about what you do!



Step 3: Rebuild your portfolio.

“Do not seek praise. Seek criticism.” –Paul Arden

Treat this process as a way to take a clear look at what you have done and where you want to go. It took me 3 months to research different designers and their specialities, and then rewrite, reformat, and recreate assets in my portfolio that were previously intended for other architects to hire me. I won’t lie to you: this step was hard but it paid dividends down the road.

Focus on storytelling, being brief, showing user research, prototyping. I was able to showcase my sketching, diagramming, and visioning process to explain how my experience as a strategist is valuable to any design process.

Collect and scrutinize portfolios of designers/thinkers that you admire. This is your secret garden. Steal like an artist- attribute their work as a starting point and make it your own. Analyze their format and tone; harvest the elements that are relevant to the type of work you do.

Your portfolio is your front door, where people make their first impressions about how much you care about what you do and how thoughtfully it’s presented. For months, I have struggled at this step, simplifying, refining, crafting and redrafting my message. This is the hardest part- the soul-searching, the self-doubt, and staring down imposter syndrome tete-a-tete. Remember that you’re thoughtfully building a bridge between who you are and where you want to be- with your secret garden to light the way. Design your story for the work you want.

Get feedback on your message and content. Does it make sense to someone outside your industry? Get as many perspectives as possible. Do not stop reworking your homepage until you’re consistently getting the intended responses.

Free up a wall to help visualize what’s ahead. Surround yourself with what you’re learning, what’s inspiring, and what you’ve set out to do.

Check analytics. When I was applying to jobs, I could see where people were spending the most time on my site, and how they navigated it. Use this data to adjust where you place important content. Prioritize pages that people see first or navigate to next. Give people a way to move on to your next project without going back. (This exercise is a great lesson because you are doing user experience design on your own portfolio. How meta!)

Ask people who know you if you’ve represented your strengths well. Focus on describing what you do well and where you fit into the new industry. This is the only place in the whole world where it’s acceptable to toot your own horn. Don’t sell yourself short on the only site truly about you.

Backplan- what are the steps to get you where you want to go? I made a 12 week chart with post-it notes to set weekly goals, focus areas, and mantras to sustain my morale.

Set stretch goals- whatever you go for, it’s gotta be big enough to be worth doing, bold enough to quit your job for.



Step 4: Document your journey.

“The work you do while you procrastinate is probably the work you should be doing for the rest of your life.” –Jessica Hische

This is super important because it will make you feel like this whole process isn’t a waste of time. Capture everything you’re doing and learning. Take it from Gavin Johns, who first showed me his amazing spreadsheet at a crowded bar in San Francisco last winter. I could feel his dedication as he navigated around the columns and rows of opportunities he was in the process of evaluating. I came home and immediately expanded on this idea and designed my own.

Since the ultimate goal is to get a new job, the main sheet to create is a way to organize companies and the jobs they offer. As I learned more about the nuances of experience design, I categorized every design firm that I learned about into: Digital Product & Brand Strategy; Experience & Environmental Design; Architecture & Interiors; Research & Design Strategy.

Include basic info like location, any contacts you have at the company, and whether you applied or got an interview. Then the most important part of this exercise is to carefully read the descriptions of the position (or their work) and identify what your skillset gaps are. You have to be honest with yourself so you know how to spend your time going forward. Finally, I liked that Gavin had a “Desire” column to gut check how much his heart was leaning toward each company/role.

My first draft is a database in Numbers, but I’m migrating to Airtable because of Gavin’s recommendation.

Other sheets I created:

1–1 Meetings: Name, Organization, Date of Meeting, Usable Advice, Thank Yous (The list is now 75+ people long).

Events: Name of Event, Date, Lessons Learned, New Contacts

Projects: Self-initiated, personal goals. I tracked: portfolio to-do’s, freelance gigs, business opportunities, competitions, courses, volunteer efforts, audiobooks/books read, recipes tried, fitness activities, art projects attempted, bootcamp ideas

With so much information on the Web, it’s possible to teach yourself a lot of what you need to know to get your foot in the door. Absorb everything until you’re speaking the lingo and can talk about where you’re going with heart and fluency.



Step 5: Quit your job.

“Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives.”

― Daniel H. Pink

My friend and neighbor Shelby helped me see what I could not. Her encouragement and willingness to be a sounding board inspired me to propose changes and finally take the leap to quit. Find a Shelby to support you as you take this big step.

My friend and neighbor Shelby helped me see what I could not. Her encouragement and willingness to be a sounding board inspired me to propose changes and finally take the leap to quit. Find a Shelby to support you as you take this big step.

I would never have been able to devote enough time and energy into building connections until I absolutely had to. This means that I went full force for 6 months, with the goal of talking with anyone who was doing something interesting in the future of design.

I left my job on relatively good terms. I knew it was time to go when I realized I’d rather be out networking than confined to my desk. The design community is small. If you can’t craft a new role at your current firm, leave before you’ve spent all your social capital and turned sour.

I had some savings. I borrowed money. I Airbnb’d my place. I swapped for services. I air-dried my laundry. I was a research participant. I freelanced as a Squarespace web developer. And I did a deep #konmari of my condo to sell my excess online. I lived on half of my previous salary by being meticulous about what I spent and using hella coupons, free trials, and promotional codes.



Step 6: Get the f*ck out there.

“We all walk around with all this knowledge that we don’t share, for fear that everyone else already knows.” — Jim Butterfield

Literally go to every event that you’re curious about, but never had time to go to before. Time is your friend now, you get to decide what you’re doing every waking moment.

Take a stand for something big.

Take a stand for something big.

I became more politically active, volunteered for organizations that I cared about but never got involved in. I peered into seemingly random Meetups, Slack Channels, and happy hours of related industries that I think are doing interesting things. Were some of these events dead ends? Yes, in that I decided not to follow the path they offered. But they also helped me figure out the direction I wanted to go. They helped me ask some important questions.

What are you trying to do? What do you believe in? What do you think is possible? When you know who you are, it’s easier to find people who care about the things you do. The more you tell your story, and learn what resonates with people, the more compelling it becomes.

Sign up for free webinars and trainings from industry leaders. Read newsletters of organizations that align with your mission or make you happy. Show up to as many events relevant to your industry in your city and milk them to get face to face with as many new people as possible- it’s on you to fill your calendar. Look for people who have similar backgrounds as you, and have taken a different path. Get good at cold emails. Reach out to people who have your dream job and ask them about their journey. Be persistent but not annoying. Turn on the “Career Advice” option on LinkedIn and follow-up with those suggestions with a genuinely open mind. Update your LinkedIn bio/blurb. Support others- offer to help their cause, buy them coffee, or connect them to your network.



Step 7: Honor those who have helped you.

“In the end, only three things matter: how much you loved, how gently you lived, and how gracefully you let go of things not meant for you.” — the Buddha

No matter how far you go, you didn’t get there alone. People have been working behind the scenes helping you find your next step, whether you believe it or not. Do what you can to express your gratitude for their support and advice navigating uncertainty.

A tribute to my many mothers.

A tribute to my many mothers.

My lowest point was when I didn’t know if I should invest in extra schooling and whether I would have to move to a new city to find my optimal career path. It was a scary time where I had to dig deep and consider what I was willing to give up, and how far I could stretch the dollars I had. (In the end, I decided that I could bootstrap my own learning trajectory and manage my way forward in a one-week self-driven sprint.) If you feel like you need the structure- invest in yourself! It’s better to know what you need help with and take action than never start at all. Ask for help and you shall receive. Then spend the time to thank the people who carried you through the dark.

Be specific in your thank you letters about how that person went out of their way for you. Be sincere- where did it lead? Refer others to them as resources if relevant, but ask first before making introductions. Give credit to their expertise and knowledge base.

Become a mentor and share your experience. Imagine the kind of letter you want to receive one day for changing someone’s life. Write from that place.



Final Note

Even though this guide is about order and rigor in your work, you don’t have to adhere to the steps sequentially. I actually did 5, 6, 2 first, then 1, 3, 7 as often as I could, and 4 last.

No matter where you are in your career, it’s never too late to assess how you spend your time and what you want to contribute to society. If you tell your ego to take a walk, you can radically change how you feel about yourself and where your skills are needed most. I ended up taking an internship at a digital product agency to explore the tech industry and test my aptitude for management. As with most worthy ventures, it will take time to discover your potential, but if you stay open, earnestly pursue new ideas, document your learning, and take time to reflect, you’ll find that you already have a lot to offer, and you’ll be better prepared to evaluate the opportunities that appear.

If you liked this article, I’ll be sharing resources for each step in my next post. Who doesn’t love a toolkit? Stay tuned.

I’ve also cross posted this article on Medium here if you’d like to share!

Emi DayComment