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Planning for September: A checklist

This is the second newsletter in the four-part series: Planning for September

You can read the first part here: A tool for structured thinking, for every age.


It’s August 2024. Sarah, a recent college graduate, is offered two job opportunities in September: one with a prestigious corporate firm offering a good salary and stability, and another with a small startup promising innovative projects and growth potential.

Excited by the startup's dynamic environment and the opportunity to make an impact, Sarah is leaning towards accepting the startup offer despite concerns about its financial stability.

After some consideration, and ignoring advice from her mentors and family about the risks involved, Sarah choses the startup, driven by her passion for entrepreneurship and personal growth. She is excited to be part of it and couldn’t wait to begin on September 1st!

Fast forward a few months to December 2024. The startup has been facing severe funding challenges, which have been leading to layoffs and lots of uncertainty.

It’s Christmas eve and Sarah is about to meet her parents for dinner. She is dreading about telling them the news - she keeps hearing their voice in her head “We told you so. You should have listened to your parents.”

She feels she made the right decision. But how can she defend it?

Did Sarah make a good decision?


From the information given, we don’t know. It depends.


1/ Did Sarah took enough time to decide?


Important decisions such as this one can often feel urgent as well, even if they are not, in the sense that we have a few weeks until an agreed deadline. That’s because importance and urgency are two parameters that we often confuse (hence, the underrated usefulness of the Eisenhower matrix). Moreover, the stress associated with making an important decision can lead us to act impulsively and rush to a decision so as to ‘rescue’ ourselves from the cognitive burden. We’ll decide and be done with it, or so we think.


But we need time for two reasons. The first one is obvious – to investigate our options as best we can, by looking into the companies, talking to people, and other ways we can get helpful and credible data. To be analytical, and have the chance to use a decision tool (like this one) to help with our process.

And secondly, to give time for our emotions to settle. Making decisions when we're is emotional can lead to hasty or irrational choices that we might later regret. For example, a natural emotion for Sarah to experience regarding the prospect of working at a start-up would be thrill and excitement. But these emotions, if they are not allowed time to settle, may overshadow other parts of her thinking process. Like, is the position a good fit for her? Will she be happy working long hours? What are the long-term consequences of failure for her CV?


2/ Did Sarah stay true to her own values and objectives?


Getting advice from people who care about us is a blessing (one we shouldn’t take for granted). It’s an invaluable resource of information. Family members and mentors often have more life and career experience and their perspectives can provide insights into factors we may not have considered, or potential consequences we may overlook. They may share their own career decisions and mistakes, offering valuable lessons that can help us avoid similar pitfalls or make adjustments to our approach. And since they are not as emotionally invested in the decision as we are, they can think more clearly.

However, while their advice is valuable, ultimately, the decision should align with our own goals, values, and aspirations. Friends, family and mentors will give us feedback and advice that is tainted, like everyone else’s, by their own life experiences, values and mental models of how the world works. As such, their advice should complement, not replace, our own reflections and research.

3/ Did Sarah have a back-up plan?


The uncomfortable truth is that we can’t escape uncertainty. We can only control our own actions (for Sarah, how much effort she puts into making the start-up a success) but outside factors and luck (competition, others’ efforts, unforeseen events) can often determine the outcome.


But we can manage uncertainty. We can make sure we stay prepared and form back-up plans for the foreseeable risks (like the start-up facing financial difficulties). Backup plans offer resilience and preparedness in the face of uncertainty, enabling us to recover quickly from setbacks and continue moving forward towards our goals.


Now what? A checklist for the full picture

Focus on what you can control. Remember (and remind others) that a good decision does not depend on the outcome, which is not in your full control. Its quality depends on the process you use to make the decision and how solid that process is.

Take the time. We need time to think things over (or relax and let our unconscious do the work) and allow ourselves to feel the full spectrum of our emotions regarding this decision. Emotions are data to consider. They are not mandates telling us what to do, but they are one of the most useful pieces of data we can possibly gather.

Stay true to your own values and objectives. Consider input from family, friends and mentors alongside other factors and your own research to make a well-rounded decision. Their advice should complement, not replace, your own reflections and research.

Form back-up plans. Once you decide, commit to your decision. But before you decide, consider that things may not work out the way you expect them to. What back-up options can you think of in advance?


P.S. From your experience, what else would you add to this ‘September decision’ checklist?

What’s a ‘September decision’ (or more generally, a new beginning) that you can use this checklist for?

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