Looking for a Career You Love? Follow These 7 Steps
How I jumped off the corporate ladder and charted a new, more fulfilling, path
Not too long ago I found myself waking up in the middle of the night with anxiety about work. Even though I had several years at the company under my belt and had built great relationships, the never ending to do list and the pressure to keep both clients and team members happy started to affect my mental health. I exercised, I meditated, I went to therapy, I job crafted, I delegated, I learned how to say no, I focused on the positive, I opened up to my manager, I set boundaries, and I practiced gratitude, but I still couldn’t get rid of the tight feeling in my chest.
My body was telling me what my mind had a hard time admitting: it was time for a change.
I’d reached a point in my career where, with my MBA and experience managing teams and scaling markets, I was often getting recruited to do something similar at other tech companies. Meanwhile, I truly loved my team, building in my company’s mission, and was so appreciative of all the experience I had gained. But neither a new, more prestigious job, nor more responsibility or pay at my current company felt compelling.
I realized that you know it’s time for something different, when no amount of money and no promise of promotion excites you.
Once I accepted that a change was necessary and inevitable, I started to get excited about the possibility. It gave me the same feeling I had when I first moved to New York in 2012; I felt exhilarated by the endless options after living for years without the semblance of any.
I could write! Start my own company! Work at a bookstore! Become a barista! Volunteer at a food bank! Travel! Go back to school! Make art! Read! Do nothing at all even!
I wanted to do everything at once. That is, everything except continue to climb the corporate ladder. But where to start?
It took some time to figure out what to do with my time and how to best leverage my strengths, but the process of discovery was worth every minute.
I now wake up happy, literally every day. Every single morning for the past year since I left my job, I have been excited to get to “work”. Best of all, it never feels like I am “working.” I have no shortage of motivation. I truly love what I do now.
It’s been nearly one year since I left my job. With the approaching anniversary, I’ve been reflecting on all that has changed since, including how much happier I am, so it felt appropriate to write about my transition process, in case it can be helpful to others.
Step 1: Catalog Interests and Opportunities
I started by listing all the things I’ve ever been interested in doing. For me, this list included everything from marine biology and psychology, to teaching and writing. It also included concepts like preparing students for the future of work and closing the opportunity gap, entrepreneurial ventures like building a business around my coffee addiction, and creative projects like making a documentary.
If you’re struggling to even think of what you could do next, I suggest setting aside a morning, turning your phone off, and taking time to reflect on these questions:
- What did you want to be when you were a kid?
- What activities did you enjoy before you started your career?
- What types of tasks or activities do you not get bored doing? Even better, what types of activities do you lose track of time doing?
- What causes or communities do you feel drawn to support?
- Who do you look up to and why? What common threads can you identify among your role models? E.g. Are they storytellers? Advocates? Entertainers?
Step 2: Take Inventory of Strengths
Before my last day at work, I sent a request for feedback to 35 team members who I had worked most closely with. I wanted to get a range of perspectives, so I sent the list to peers, direct reports, and people who were senior to me at the company. I asked the following questions:
- What seems to come naturally to me
- What are my standout strengths
- Where do you see the biggest opportunity for me to make the most impact
- Close your eyes and imagine me in 10 years — what do you see
- What could I change or improve upon to have more impact
- Before reading that feedback, I made my own list of my skills and strengths. Then I reviewed the feedback I was sent, combined common words into themes, and counted the number of times each word in that theme was mentioned in the survey responses. I starred anything on my list which stood out as a theme, and added to it when more than one person mentioned something I had missed.
In the end, my list looked like this:
- relationship building: connecting, empathetic, approachable, personable, relatable, caring, compassionate, community building, understanding (76)
- leadership: big picture thinker, strategic, vision, problem solving, action oriented, collaborative, empowering, encouraging, motivating, mature (63)
- attitude: passionate, enthusiastic, friendly, positive attitude, charismatic, outgoing (58)
- work ethic: driven, committed, hard-working, follow-through, resilient (48)
- communication (25)
- authentic, genuine, natural (22)
- calm, relaxed, balanced, patient, flexible (19)
- intelligent (15)
- attention to detail, organized, time management, prioritization (13)
- confident, decisive (13)
This process was illuminating for several reasons. I knew I was good at building relationships, but honestly, it came so naturally that I didn’t ever think of how much it stood out to others. I wouldn’t have mentioned it as a top three strength in a job interview. And I wouldn’t have thought “hmm, maybe I should make sure my next job has more relationship building opportunities.” I also realized that many of my insecurities weren’t founded in reality. I was always worried I wasn’t doing enough, that my effort wasn’t creating a meaningful impact. The crowdsourced feedback clearly showed otherwise.
Given how affirming and clarifying it was to get this feedback, I wish I had gone through the exercise before giving my notice. I now would recommend that anyone who is even thinking of quitting their job do this first!
If you aren’t in the position to gather feedback from co-workers, and don’t know where to start with identifying your own strengths, don’t be afraid to ask your friends and family what they see as your strengths! You can also take the StrengthsFinder assessment, 16 Personalities, Principles You, or any number of other free self-assessments available online.
Step 3: Reflect on my Values
The final part of my reflection involved getting more clarity around the work I wanted to do, so I could make sure that anything I spent time on was aligned with my values. What is the point in finding out that I am good at building relationships if I just use that to sell something that leaves the world worse off?
If you asked me before what my values were, I would have given a rambling answer. I knew I valued impact, relationships, and equality, but wouldn’t a Trump voter say the same? I heard about the Value Sort exercise from a podcast by the former Dean of Students of the business school I attended.
According to the Good Project website: “knowing what we value most in our work, relationships, and other commitments makes it easier to respond to opportunities and conflicts with integrity.” The activity involves narrowing a list of 30 values down to your top 5. It was a tough, but again, illuminating exercise: all the values are ones which I “value”, so it was not easy to narrow down to my top five which were:
- Personal Growth and Learning
- Understanding, Helping, Serving Others
- Openness, Receptive to New Ideas
- Rewarding & Supportive Relationships
Once I had a better sense of my top values, I asked myself:
- how do these values align with my list of interests and opportunities (from Step 1)?
- how do these values align with my strengths & skills (from Step 2)?
- given all of the above, what does this tell me about the legacy I want to leave behind?
From these answers, I developed a mission statement:
My mission is to build global communities that help to democratize access to opportunities.
Step 4: Create Filters
Even with a mission statement, my list of interests and options was overwhelmingly long, so I created a counter list of filters to start eliminating some options. For example:
- I did not want to go back to school at this point in my life (this immediately eliminated becoming a therapist or doing a Ph.D.)
- I did not want to commit myself to something that would require 2+ years to see the result (bye novel!)
- I did not want to mistake a hobby for a career and risk eroding the pleasurable aspects of the hobby (as much as it pained me, this allowed me to cross off working at a cafe or bookstore from my list)
Step 5: Create Scorecard:
With my short(er) list of interests and opportunities, and a comprehensive list of strengths and skills in hand, I developed a a scorecard to help prioritize where I should focus my attention over the next year.
The scorecard is inspired by the concept of Ikigai — a Japanese concept meaning ‘a reason for being’. The basic premise is to lay out what you love (step 1), what you’re good at (step 2), what the world needs (criteria in Step 4), what you can be paid for (criteria in Step 4), then find the overlap.
For my scorecard, I used the following criteria (mostly aligned to my value-sort activity):
- Impact Potential (Understanding, Helping, Serving Others)
- Fun Factor (Openness, Receptive to New Ideas)
- Financial Sustainability (Independence)
- Network Building Potential (Rewarding & Supportive Relationships)
- Springboard for Future Projects (Openness, Receptive to New Ideas)
- Learning Opportunity (Personal Growth and Learning)
- Connection to Strengths/Skills/Mission Statement (Ikigai)
Step 6: Analyze Results
This exercise helped clarify for me that many of the things I wanted to do either had very uncertain financial returns (like writing a novel), or weren’t very well aligned with my skills and strengths (like creating an online course). It also highlighted that some of the work I was interested in doing wasn’t really what the world needed (like creating a photobook or doing voiceover work).
Some of my interests were much better suited to be hobbies than career paths; I concluded that I could always try to include scuba diving in my vacation plans instead of continuing to wonder if I should become a marine biologist, and I could continue to enjoy visiting coffee shops instead of opening one of my own.
Some of my opportunities and interests were harder to score though. A documentary film could potentially have a large positive impact on the world, but does the world really need more content to consume? Shouldn’t we move from the “learning about” phase of human trafficking or climate change into the “doing something” phase? And would the amount of time and money required to see a film through initiation to post-production be worth it? Or would a simple Medium post or podcast do the trick? The potential cost and return were very uncertain, but still, I found myself trying to keep this path from being eliminated on my list — data in itself.
In the end, my prioritized list looked like this:
- Consulting venture-based ed-tech startups aligned with my values & mission
- Angel investing + advising early-stage startups
- Community management at an organization that aligns with my interests
- Offering leadership workshops
- Documentary filmmaking, but focused on shorts
Step 7: Start Testing
It would have been easy for me to take this short list as a guide for the next ten years of my life, but my experience of once trying to become an influencer (I firmly believe that I have visited more coffee shops than anyone else, and I once thought it would be great to share those visits on @newdaynewcafe. It only took two Instagram posts for me to realize I hated everything about this path!) told me that actually testing these potential paths would be critical.
There’s no short cut here: to test, you must simply start.
I recommend starting small, and focusing on the actual work you’re interested in, not the busy work around that.
For documentary filmmaking, that meant just picking up my phone and filming a subject that interested me, and reflecting on how that felt. It did not mean figuring out how to raise a million dollars or setting a goal for myself of having an Oscar nominated feature length film that gets picked up for distribution by Netflix.
For consulting future of learning/work startups, that meant looking for nascent start-ups in this space on Angel List and reaching out to founders to introduce myself and offer my help. It did not mean creating an LLC, building a website, or cold calling more established companies to pitch my services at at $250/hour.
I focused on one career path at a time, testing these different options for almost a year. Remember my top 5 values and my mission statement? I kept those top of mind every day to remind me of my big-picture goal:
- I made sure not to put pressure on myself to commit to it long term (Independence)
- I constantly reminded myself that it was ok to feel uncomfortable when change was the goal (Openness, Receptive to New Ideas)
- I reassured myself that learning was a desired part of the process, and something I highly valued! (Personal Growth & Learning)
- I made sure that along the way, I prioritized developing authentic relationships in the future of learning and work space (Rewarding & Supportive Relationships)
- Finally, I focused on the long term potential for impact I could have (Understanding, Helping, Serving Others)
One year, and twelve career tests later, I couldn’t be happier with the decision I made to leave my high-paying, high-status job. I am now in a position where I honestly do not care if I make any money, but the beauty is that I actually earn more than I did before, when I was making myself sick thinking I wouldn’t be able to make as much if I left without a plan. I feel like I have more options than ever and have learned so many valuable lessons. But most important of all, I feel like the best version of myself again, which is really what it’s all about right?
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