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Self assessment

Six steps to discover a career you love

To plan your career, you need to know where you’re going. What’s your goal — your dream job? 

Articulating your dream job is important for two reasons: 

  1. You can’t navigate your career unless you know where you’re going
  2. Knowing your ideal roles can help you see what you really value, which makes every step in your career much easier (and every role much happier) 

So I’d like to share a simple exercise to help you uncover your dream job — and why.

Step 1: What dream jobs would you be happy doing for the rest of your life? 

These should be jobs that are exciting, that fill you with energy. It’s OK if you’re not entirely sure about what they entail. Just list them out. When I last did this exercise, they were: 

  • Tenured professor at a business or policy school 
  • Head of a foundation that gives away $100 million each year
  • Venture capital partner 
  • NY Times columnist 

Step 2: Diagram these dream roles

For each of these, list out the activities and characteristics of the role that give you energy, as well as anything about the job that sounds horrible. For example:

RoleEnergizing Activities Energizing CharacteristicsDraining Activities / Characteristics
Tenured professor-Formulating research ideas-Learning about new areas
-Discovering new knowledge in research
-Writing articles / books that change how people think and behave
-Ability to choose projects-Discrete projects to work on
-Ability to choose collaborators-Ability to constantly learn
-Ability to have an impact by influencing people
-Dealing with petty department politics
Head of foundation-Creating a strategy to have an impact
-Making funding decisions 
-Implementing programs to support great, high-impact organizations
-Ability to have an impact-Thinking about 
-Platform for influencing many other people
VC Partner-Learn about lots of different business models
-Learn about sectors and form investment hypotheses
-Create a differentiated thesis and brand, based around applying research /science
-Coaching / advising entrepreneurs
-Constantly learning-Strategy has a lot of leverage — picking right investments, making right decisions
-Ability to advise / influence entrepreneurs
-Self-directed
-Raising money from LPs
-1000s of emails each week
-Being on the board when things go badly and get brutally political
NY Times Columnist-Learning and exploring new ideas-Writing-Ability to influence the way many people think and behave

Step 3: Distill commonalities of your dream jobs

Then, look at the activities you’ve listed out — what are the things all of these roles have in common? For me, these are: 

  • Learning
  • Thinking strategically — i.e. making a case for how to deploy resources to accomplish a goal
  • Influencing people through writing, discussions or dealmaking

Then do the same for the characteristics: 

  • Autonomy — ability to choose what I work on, whom I work with
  • The ability to work on discrete projects
  • Ability to have a big impact on the world
  • Working through influence

And the things I really don’t like are: 

  • Politics — i.e. making decisions based on organizational or interpersonal constraints rather than what’s the best way of pursuing our goal
  • Being distracted from deep thinking
  • Having to micro-manage people through the easy parts of their jobs

Step 4: Map the paths

Next, try to think through what job or accomplishments would allow you to get each of these jobs, and try to plan backward from there to where you are now: 

ProfessorFoundation headVCColumnist
Paths to the job-Top PhD-Research + publications for tenure
-Successful business or policy career
-McKinsey partner
-Successful Entrepreneur
-Nonprofit CEO
-Successful Entrepreneur
-Career as VC-Research commercialization of science, lateral into investment
-Professor
-Writer
-Successful at career + demonstrated ability to write
Requirements to get the job-Lots of publications in top journals
-Dramatic accomplishments in career
-Network with foundation boards, billionaires
-Credentials/experience for domain
-Social impact accomplishments
-Dealflow — ability to get lots of good 
-Network of great entrepreneurs
-Differentiation among entrepreneurs
-Investment track record
-Credibility — why you? 
-Track record of writing-Distinct POV

Ste 5: Evaluate the paths against each other

Based on the analysis above, think through each of the ideas. Ask yourself, “How does this path stack up compared to the others, based on the time to succeed, the likelihood of success, and how enjoyable it would be along the way?” 

  • Academia. Clearly bad for me. Takes 15 years, and you have to write for academics not practitioners. Low chance of success (if you get into a top PhD program, 30% you get a top tenure-track job, 50% you get tenure). 
  • VC. Interesting, though working as a VC doesn’t necessarily have an impact, which might bug me for the 5-10 years it takes to get to the point where I could raise a fund. 
  • Entrepreneurship. Very interesting: this allows all of the other options and is the most enjoyable/interesting along the way. 
  • Consulting. I think the politics of working within a big institution and for other big institutions would drive me crazy. 
  • Nonprofit. Could be interesting in the right organization, but the dynamics of fundraising would annoy me. Feels similar to entrepreneurship, but generally a worse option —  a mission-driven for-profit has all the benefits of a nonprofit, plus better comp, more funding, faster growth. Major advantage here is that you have more problems accessible to solve. A good option could be to develop skills in startups and apply as senior leader in growth-stage nonprofit like One Acre Fund or Give Directly.
  • Writer. Would be very interesting, but not if you had to earn money to make a living. Could work in tech for 5 years, save enough money to not need to work. Or could potentially combine writing with a lifestyle consulting, to make enough money to keep writing. 

For me, continuing to work as an entrepreneur made the most sense. 

Step 6: What’s next? 

Now you have a general direction, and an understanding of why some paths are better than others for you. But, as you look for specific jobs, ask yourself which ones build the skills and accomplishments required for your dream job. For me, this included: 

  • Proven ability to write
  • Tangible accomplishments 
  • Work with high strategic leverage
  • Ability to save money
  • Entrepreneurship with high probability of success and short time to success

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