Is Career Optionality Good or Bad?

Optionality feels exciting. People love having optionality in their careers. It provides a unique sense of power that they get to decide what to work on and where to spend time. 

Earlier in your career, you’re constantly trying to portfolio manage your risk. Jumping from one job to another every 24 months to seek a better title, better brand on your resume, and slightly more compensation. Your friends constantly ask you “what’s next?” at happy hours, and your mind is constantly searching for the next ladder. This cycle continues for a few years and then you realize that most changes were horizontal in nature; diagonal at best. 

To build anything meaningful, you need to focus and commit. You can’t build anything important in 24-36 months. It takes years to solve hard problems and a relentless mindset that’s focused. 

Portfolio managing your career enables you to go mile wide, but inch deep. 

Earlier in your career, it makes sense to explore new opportunities across different categories, companies and teams. After a few years, it’s a good idea to settle down, focus and commit to solving problems that you care about. 

Optionality is rewarded earlier in your career which gives you a hall pass to jump around. The opposite is also true. People earlier in their career that stick around will have greater sets of opportunities within an organization. Companies reward loyalty and tenure.

Generally speaking, the privilege of jumping around starts to diminish as you get later in your career and seek executive positions. CEOs want execs that will commit and stick around for the long run and to ensure they’re here when things get tough. There’s a reason why board members push to having most executive comps tied to stock programs and vesting schedules. It’s a forcing function to get people to stay.

So, is career optionality good or bad? 

It depends on the stage of your career. It’s probably good to have some optionality earlier in your career. It’s bad to jump around later in your career. My recommendation is to find those career moments in your current job; and if it doesn’t exist, then try to create them. This is a better path to pursue than to simply jump to the next gig.

In either case, I encourage you to proactively create a career framework for yourself. The difference between living life and leading life is having a proactive mindset of planning. 

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