In the process of trying to plan better, I realize that I end up underestimating the amount of time that it takes me to do something, and overestimating what I can get done in a given period of time.
From talking to friends and colleagues, this appears to be a common observation, including by people who we might consider as successful.
The name for this is Hoftstadter’s law, or the planning fallacy. We tend to consistently blow past not only our best case scenarios for how long things take, but also our worst case scenarios.
What’s the solution? One option is to try a ‘premortem’. Assume things have already gone wrong and you missed your deadline. Ask yourself what happened and what went wrong, and then plan accordingly.
In the words of Daniel Kahneman (though the exercise is attributed to a collaborator, Gary Klein), ““Imagine that you are [X amount of time] into the future. You implemented your plan as it now exists. The outcome was a disaster. Take five to ten minutes to write a brief history of that disaster.”
Applying this to my life
To apply this to my life, I have to think about some of the goals I have, and think about some point in the future. In the next section, I’ll run through the exercise with one of these goals.
Here are some goals I have:
- have a source of income that pays well, is flexible enough to meet my lifestyle needs, I am good at it and enjoy it enough to do sustainably, and am getting better at over time and am gaining more responsibility as time goes on
- get better at writing by writing consistently
- improve my French, be able to have short conversations in Arabic, and be able to read Telugu
- exercise everyday
Example pre-mortem
So let’s think about the first bullet point – having a source of income that pays well. Let’s imagine that in one year, in December 2023, I’m unemployed and sitting in my parents house. What went wrong (and how would I prevent that from happening)? Here are some ways it could have all gone wrong:
- I took a job for the sake of having a job, even though I wasn’t a good fit for it, and it ends up not working out (and thus I’m unemployed again)
- I should identify what environments I would not do well in, and be very insistent on not joining a company that matches that description – even if it’s scary to continue searching
- I interviewed for a few jobs but didn’t like any of them
- I should be specific about my non-negotiables, but be open to taking an opportunity that doesn’t fit them as long as I can do the job sustainably and am learning something
- I apply to hundreds of job applications but I don’t hear anything back from anyone
- I should focus on job listings where my skills and experience are compelling enough to stand out in a pile of resumes
- Better yet, I should focus on identifying opportunities where I have connections, or leveraging my existing network
- Additionally, I could opt to do a “bridge job” while I continue to job search, where at least I would be able to get out of the house, and generate some money
- I get first interviews with a number of companies, but don’t progress to the offer
- I should identify gaps in my interviewing skills and fill them
- Or, I might be putting opportunities into my funnel that don’t match my skills, and that only becomes clear during the interview phase
- Perhaps I lose enthusiasm or steam between interview rounds, or get too optimistic and thus don’t prepare well enough
- I keep changing my mind about what I want to do, so that once I start getting into the interview process for one company or role, I lose interest and pursue something else – thereby never committing to anything
- I should prioritize what I want to do and remind myself to not be a perfectionist, instead focusing on whether or not the opportunity will help me towards my next step
- I should set a hard deadline and decide that whatever I get by that day (or whatever I decide to do by that day) is what I’ll focus on. If I really hate it, I can always get a different job or change my roles
- I decide not to search for a job, and instead try to build my own company, or try to sustain myself with a variety of income streams. It fails miserably and I’m broke
- I should identify what is necessary to be your own boss, and be realistic about whether I would be good at that. More precisely, I should test it out and see how well I do
- I should also be realistic about how each of those income streams can scale and grow – is there enough margin for me to live comfortably? Or even in the best case scenario will I be barely scraping by and stressed?
- I should also think about why building my own company or doing a variety of income streams appeals to me – is it because I’m well suited to that kind of lifestyle and it’s how I’ll provide value – or is it because I’m trying to escape something? Can I address the underlying emotions first?
Conclusion
Hopefully this helps you plan better for the future, and do your own pre-mortems. I can’t promise that it will cause everything to go according to plan, but hopefully it will help you identify some challenges you didn’t think about before.