Career Path Metacognition

I’m at another fork in the road, this time 9 years out of college. I’ve had good experiences (EB IB, MM PE, CFO of a portco), which allow for a range of next steps – e.g. back to PE, GE, IB, new ops job, ops consultant, start-up, et cetera. But I’m having a tough time thinking through what to do next – I like some aspects and dislike others of each of those career paths.

I’m sure there are others who have been through this “end of the first quarter” career dilemma – you have meaningful experiences and connections to leverage, but are still not so far along in your career that changing careers loses too much momentum to make it worth it under normal circumstances.

So, I wanted to open up a thread to discuss what people would be thinking about at this point in the game. What questions would you ask yourself? How do you get to “know thyself” – what you enjoy doing and what motives you? What advice would a sage provide to someone at this point?

I’d like to avoid going into the details of particular career paths (e.g. PE vs. IB vs. vs Ops vs. Corp Dev, etc.), which are fairly well covered on this site and likely covered by personal experience/network at this point in our careers. Instead, focusing on the thought process that can then be applied to general knowledge of career path particulars.

Some ideas as an example and to get things going:

• What sort of work-life balance do you want over the next 5 years, and the 5 years after that?
• How much autonomy do you want over the next 5 years, and the 5 years after that – working under someone (have someone to learn from (good), not hold all the responsibility (good or bad), be on their schedule (bad)); vs.  its “your party”, if you will. As someone who has led a company, more autonomy/responsibility isn’t necessarily always more fun – sometimes its nice to be able to do your part and then go home…  
• How much money do you need to do the things you want to do in life? House, city, children, travel, cars, etc. At what time in your life do you need that money?
• How much risk are you willing to take? And what are the areas of risk – Financial Risk (lower cash comp but potential carry/equity); Career Risk (get stuck somewhere and have limited optionality), etc.
• Do you like a structured work environment, or one where you must wear multiple hats every day?
• Do you like working in teams or independently?
• How much do you like selling / sourcing?
• How much do you like getting in the weeds?
• Does your ego need a “prestigious” job?
• Do you have outsized career momentum (e.g. experiences, network) in a particular direction?

I recognize that this thread may not be for everyone, but hopefully there are some thinkers among us who can share their wisdom.