As we gain experience, there are fewer roles that fit our skills and we lose the energy for big cross-functional / managerial roles. Eventually you start asking “what is next?” and want more control over your destiny and lifestyle
Career 2.0 is defined as what do you do once you stop doing big cross-functional executive roles but want to keep working and making money.
Overall Considerations
Before you take the plunge on Career 2.0, here are some things to consider:
What gives you energy? While many of the flavors of Career 2.0 sound good intellectually, you need to be careful not to work your way into a job you don’t want
Do you like to sell? Some of the solo options for Career 2.0 require you to be selling yourself
Do you like to roll-up your sleeves? If you are going to be running some businesses, you may have to get your hands dirty
"It is extremely puzzling that in a world where a lot of people can cover the basics (food and shelter) they still spend the grand majority of life doing things they don’t like doing. I think a lot of it comes back to not really understanding what your true desires are. I think most people wish that they like things they don’t actually like. I think a lot of people wish they wanted to make more money than they actually do. …. Most people are in denial about what they really want." Jeremy Giffon on Invest Like the Best podcast (link to key part)
Do you want to sell time or impact? Some Career 2.0 roles revolve around selling your time. Fun article on AI trends here
Do you have health care covered? Until 65 you have to take care of this yourself. If you don’t have a spouse whose career provides this, are you ready to cover it yourself?
Are you ready to commit? Once you take the step to Career 2.0 it is difficult to return to full-time work. Folks in many of the paths below report their skills (and networks) get stale if they step out for too long.
Flavors of Career 2.0
Below are the traditional flavors that people think about when they start thinking about their career 2.0. We are writing deeper article on each and will add them as they are complete:
Fractional / Consultant: Providing advice on your area of expertise typically by the project or by the hour.
VC Operating Partner: Advising portfolio companies on your area of expertise
Coach: Helping others on their journey. Typically charging by the hour.
Boards: Sharing your advice with other executives
Search Fund: (coming soon) Buying a business
Investor: Investing in great companies
Thought Leader: Creating content and courses around your area of expertise
Recruiter: Leveraging relationships to help companies find great talent
Use these flavors as starting points, not manuals. Most people find their Career 2.0 not by picking one of the standard flavors but by finding a variation on one. Whispered has been that for us.
To find your Career 2.0 DO NOT overthink it. Don't create a powerpoint. Just find something you are intrigued by and start working on it. By moving forward, you will discover new insights and paths constantly.
At the same time, be thoughtful. Sometimes when you make your passion for job, it can become less fulfilling.
"Making something a business is a great way to hate that thing. If you surf to relax on Saturday mornings, that is very different than being required to wake up at the break of dawn to take cantakerous ibankers surfing". Tim Ferris (see podcast full discussion here)
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