Career Anti-Planning

‍

‍

If you’ve read my book or other writing, or heard me speak, you’ve probably heard me talk about career planning. It’s a very important skill; one we really need to teach more formally. Today I’m going to talk about career anti-planning. It’s a useful skill which can be applicable at a variety of stages.

Students and early adults often don’t know exactly what they want to do. I have a series of starting career planning questions (as in starting questions for the process, not questions solely for starting a career). Even so, people often don’t have answers to some or most of the questions. That’s ok, not everyone knows what they want to do when they grow up; this is where anti-career planning can help.

To anti-career plan, invert the question. Often, it’s easier to answer the negated form of these types of questions, that is, what you don’t want. You may not know the answer to, “How much travel do I want?” but you may know, “I definitely don’t want to be traveling 100% of the time.” In fact, you might think, “I probably don’t want to travel more than 50% of the time, although maybe for the right job, but even then, not more than three out of every four weeks.” OK, we just found an upper bound on work travel for you.

For, “Are there any ethical or moral considerations?” maybe you simply draw the line at things you don’t want, e.g., “I don’t want to make weapons.” This could lead to a related question: what if you work at a service organization whose customers are in defense, how would you feel? Would you not want to work at that company, or maybe just not on that client. Even if the latter, it’s something to keep in mind when looking at jobs and careers.

Consider, “Do I want to manage people? Be managed? Be independent?” Your answer may be, “I don’t want to manage others.” It’s a start. Perhaps you even think, “I don’t like large teams or jobs where I’m in large meetings.” That’s helpful, you’ve just ruled out jobs that have big project teams with lots of coordination meetings.

You can apply this to a job choice as well. When deciding between two jobs you value similarly, it can be hard to know which job to take. The anti-question would be to look at it in reverse: which job are you more likely to regret not taking? Fast forward five or ten years. Assuming neither company / career path option will be wildly successful (in terms of career, financial rewards, etc.), would you look back and think, “I wish I had tried the other option” more with one rather than the other?

Here the option could be trying to work internationally, working for a startup, running your own business, moving to a new city, trying a new role in industry, etc. The answer may be you were glad you didn’t. I wish I had the chance to work more overseas, but I also know that for the tech startups I wanted to do, the US was the best market. None of my companies exited (sold) so well that I can live a life of retired luxury. On the one hand, missing out on some startups and working overseas may not have cost me anything (i.e., I didn’t miss out on the next unicorn that would have made me incredibly rich). On the other hand, I probably would have looked at the greener grass of the startup world in the US and thought, “Maybe if I was there, I could have been at a unicorn company.” And while I would have liked to have worked overseas, I do not look back and think “damn, I missed an opportunity and wish I had taken that chance instead.”

I always need to take the shot, which is why I joined startups or consulted on my own. I can look back on times where I struggled to find clients, or the startup went under and know that a corporate job would have been less stressful and more stable financially. But I also know I would have regretted missing that chance. Sure, maybe if every startup was a disaster I’d feel differently, but likewise if every corporate job was soul sucking, it would be equally clear. The point is to consider if one path is reasonably better than another, how would you feel about missing out? The one you’d regret more is a choice you should seriously consider.

Anti-planning can work in a number of situations, but it works particularly well with future choices like career paths. In chapter 1 of The Career Toolkit, Essential Skills for Success That No One Taught You I show examples of how the career options can begin to branch out into an uncontrollable number of options. Anti-planning lets you prune some of those options to make the choices more manageable. It won’t take you to the final answer, but it can get you pretty far and make it much easier to focus on the few remaining questions to help narrow down the final choices (just look at the similarities and differences between the choices you have left). Let me know how this works for you. Good luck.

‍