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Career 2.0

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

  • 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 done:

  • Coach (Executive Coach, Life Coach, Career Coach): Helping others on their journey. Typically charging by the hour.

  • 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

  • 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

  • Boards: Sharing your advice with others

  • Search Fund: Buying a business


Many people find their Career 2.0 not by picking one of the standard flavors but by finding a variation on one. Another great way to find your Career 2.0 is to find something that gives you joy and keep double-clicking on it until you find a repeatable model.


Don't know what you want in your next role?





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