Keep cultivating multiple career options

I work as a tech advisor to CXOs, helping startups that are not on the path to achieving their next milestone do so, guiding management on tech, team, management and culture. I’ve contributed to a multi-million dollar outcome out of a stagnant startup. I’m growing in my career, and I like what I do. I’m not interested in anything else, at this point.

However, I do have a plan B, which is to take a career break. Freed of the obligation to earn money, I plan to upskill myself for the next decade of my career. And to achieve certain personal goals.

I also have a plan C, which is to take up a full-time job, but at a bigger scale than before, such as managing 20+ engineers or generating at least a million dollars a month in revenue. I have prepared my CV in two different formats to explore which is a better way of communicating why someone should hire me.

Similarly, you should keep exploring and cultivating multiple career options, for a few reasons:

‣ If you’re ambitious in your career, if you want to achieve a lot over the next few decades, you should consider different career options like being a cofounder of a startup, being a consultant, starting a startup or being a solopreneur. These ambitious career options are not obvious and need time to cultivate. When my startup wasn’t doing well, for the last year of its life, I explored consulting by reading a book or two, listening to podcasts, and reading blot posts. As a result, I got clarity on what I want to do as a consultant. When I shut down the startup, I immediately had something else to do.

‣ This brings us to the second reason to cultivate multiple options, which is that you’ll have a safety net if what you’re doing doesn’t work out. There are two ways to climb a mountain: with or without a safety rope. If you don’t have a safety rope, a fall will bring you all the way down. When it comes to your career, not having a plan B can make failure scarier and more psychologically damaging.

‣ Another reason why you should keep cultivating multiple career options is that comparing options gives you better clarity on what you want, not evaluating one option in a vacuum. If you want to start a startup, consider comparing that with some other option like consulting. You may pick consulting because it’s lower risk than starting a startup, and then realise that a startup was never the right option for you. You may not have gotten that clarity if you evaluated a startup as the only option on the table.

‣ Another reason why you should cultivate multiple career options is that the time may not be right in your life for a given option, but that doesn’t mean you should reject it immediately. You should plan out how to (say) become a cofounder, perhaps by deciding that you’ll join a founder looking for a cofounder rather than starting a startup yourself.

‣ Another reason why you should cultivate multiple options is that you could backport an idea or two from it to your present job. For example, if one of the options you’ve listed involves being in a position of responsibility, you could then have a conversation with your manager on what you can do to get more responsibility in your present company.

For all these reasons, keep cultivating multiple career options in parallel.