Career advice: don’t listen to it, but if you must…

For endeavoring on a career with a statistically low chance of success and being qualified for little if I fail (a good motivator), I receive a surprising number of requests for career advice. My first rule on career advice is not to listen to anyone – it is easier to give and receive advice on almost any other topic where there is a specific problem, set of options and relatively quick feedback on outcomes. Careers, however, take years to play out, are immensely idiosyncratic and are as much a matter of the heart as the mind. Career decisions lend themselves not to prescriptive advice but to frameworks that guide decisions, to be applied and ultimately answered by the beneficiary (or victim)!

There are four questions/dimensions that I think matter most in framing a career opportunity decision:

  • People: Do the opportunity’s people energize, teach and motivate you?
  • You: Are you a Judge or Builder, and does this opportunity fit your preference?
  • Immediacy: Is this a stop on the journey or a final destination?
  • Optionality: Is this opportunity “option expanding” or “option limiting”?

In visual form:


This framework evolved through my own career as follows: I went to college to EXPAND MY OPTIONS. With an engineering degree, I could have done many things (engineer, finance, consulting, academia). Not knowing much about my options, I became a mechanical engineer… seemed obvious. This was OPTION LIMITING as it’s hard to move out of the tech side of big business once you’re in.  I was lucky to learn early, however, how working with incredible PEOPLE multiplies your own experience, growth and enjoyment. By chance, my bosses and co-workers at Raytheon and GE were phenomenal. In my five years as an engineer I also found the first evidence that I am a JUDGE and less so a BUILDER. While 90% of mechanical engineers design and build stuff, I found a fit in analyzing others’ designs to see if they would break or overheat.

In 2008, I went to business school because I wanted to (re)EXPAND MY OPTIONS. Engineering was too narrow. I wanted to see how the whole business machine worked and did a number of internships in b-school – JOURNEY PITSTOPS – to learn and try new things. Several internships were in analytical investing roles, JUDGING. New to business, I wasn’t ready to pick a path at the end of b-school and so went into management consulting at BCG. This was both a JUDGY and OPTION EXPANDING decision.

Something else happened in business school. I found an incredible business partner, Ira Weiss, and the taste of an enticing career in startup investing as a venture capital intern. While Ira was the PERSON I probably would have followed into anything, fortunately we both settled on tech investing. Since 2012, I’ve been a VC, which is very OPTION LIMITING but I also hope my FINAL DESTINATION. I love it and will stick with it as long as it lets me.

PEOPLE: Much has been written about choosing the right colleagues, so I won’t go deep here, but certainly picking the right people to work with is something often overlooked amidst other factors like activity of the role, title, compensation, commuting distance, etc. Spend time with the people you will work with both 1:1 and in team settings. Talk to others who have worked with them.

BUILDER vs JUDGE is less obvious. Do you like creating products, teams, relationships or companies? Or do you prefer to review and analyze others’ work. Here are how a few professions fit in:


Salesperson – build a book and relationships

Engineer – build a product

Executive – build a team and a business

Marketer – build a brand

Startup Founder – build a company


CFO – analyze finances and judge performance

Accountant – analyze financials

Strategy analyst – analyze new opportunities

Investor – analyze businesses

HR – analyze people

Truly this is a spectrum, not binary. I do have some builder in me, and that’s why I was drawn to building a new investing firm with my partners rather than joining another. Yet 90% of what I do is judging. I’ve seen builders trapped in judge roles itching to go start something new. Fit is important.

JOURNEY vs DESTINATION is a classic tradeoff in career opportunities. Is the opportunity a pitstop on the journey to your aspiration or is this the aspiration itself? Many suffer through banking to get into private equity or work at a scaling startup to better position as a founder of one themselves.

OPTIONALITY in a career opportunity is often overlooked. Does the role qualify you for many new positions or paths later or reduce your flexibility to switch roles or careers? As an example, venture capital is one of the most option reducing careers: we don’t manage people, have P&L responsibility, create products or execute large projects – at least in the common sense. Consulting, on the other hand, is the ultimate option expanding role. Following, you can work at a big company, become an investor, jump into a startup, etc. Time in a role is also a factor; optionality tends to grow the longer you are in an option expanding role and decrease the longer you are in an option reducing role. Using my timeline this looks something like below:


It is worth remembering that optionality isn’t a measure of whether you can move to other roles or careers, but rather the ease of doing so based on qualifications, personal network and experience. Anything is always possible.

Balance the dimensions, but don’t compromise

It is best not to compromise at all on people or much on builder vs. judge fit. Giving in on those begs unhappiness, and your significant other doesn’t want to hear about it every day.

The other two dimensions (optionality and journey vs destination) balance against each other as shown below:

Img 3

In a perfect world, we would all be in the upper right nirvana quadrant – in a role we see as our final destination that ALSO creates optionality. This can happen. I know some Senior Partners at BCG and highly successful executives for whom this is the case. Most of us end up in quadrant II or IV. I am in quadrant II, happy in an option limiting role that I want very much to be my terminal career. As a consultant, I was in quadrant IV (career growth) and also happy, but there as a stepping stone. In general, it’s okay to limit options if you think you are somewhere for good, but if your stay is fleeting, you should be growing your options. Quadrant III (limiting your options on a pitstop) is high risk. Even if it’s a step on the way to where you think you want to go – a singular egress can pile up with bodies when a company’s fortunes shift or the market turns.

I haven’t mentioned money at all. If you are motivated and energized in your work, monetary rewards will follow if they are important to you.