How to make hard decisions

Hard decisions are hard for a variety of reasons. Sometimes it’s a choice between two options that are equally appealing. Other times it’s the opposite: you are stuck between a rock and a hard place. Sometimes they are hard because the stakes are so high and there doesn’t seem to be room for mistakes. Other times you feel overwhelmed by the uncertainties and risks. Often it’s some combination of all of the above.

I have been giving this a lot of thoughts lately, probably because my husband and I have had to make some hard decisions, and I have also seen some of my friends and family members going through similar struggles. Maybe it’s the life stage my peers and I are in (late 20s to early 30s) that presents us with a lot of these hard decisions, or maybe it’s just life itself. My guess is 20s is when most people start to make some hard decisions, and it doesn’t really stop from there. Hopefully as people grow and learn they become better at making the hard decisions, but I’m not sure if they ever really get “easier” per se.

Reflecting upon these hard decisions, I have come up with some insights to share:

I. Be brutally honest about what you want

  1. Identify your values. What do you really care about? Not what you have been told to care about by your friends, family, and peers (because that’s what they care about, but it doesn’t have to be what you care about). What do you really value above all else despite all the distractions and bullshit?
  2. Separate your wants from your needs (based on (1) above). Confusing your wants with your needs is what can lead you to unknowingly sacrifice your needs for your wants. This is how people get what they thought they wanted but still end up unhappy and wonder why.
  3. Assess your circumstances. We don’t exist in isolation. Our physical, mental, and emotional state and needs matter. So do our personal, financial, and social environments. They are directly tied to (1) and (2) and figuring out how they influence each will give you a lot of clarity.
  4. You can’t have it all, so prioritize and make trade-offs. Ambition and greed are not synonymous and you can’t optimize without knowing your constraints. Everyone has them; get to know yours to avoid over-extending yourself and being disappointed by reality.
  5. Know your strengths and weaknesses. Economists call this competitive advantage. We all have them – use them. Many of us are pretty aware of our weaknesses, but may not be as good as identifying all of our strengths. Here’s a long (but definitely not exhaustive) list if you are looking for some inspiration and guidance.
  6. Be aware of your blind spots. No one is omniscient. Knowing when and how to ask for help is crucial.
  7. Listen to your instincts. Your brain knows more than you think. Don’t just rely on the conscious thoughts; taking advantage of your full knowledge base means listening to the unconscious ones too.

II. Understand your options as well as you can

  1. Consider the pros and cons broadly and deeply. Make those lists, and then get more specific and challenge each item. Don’t stop at the what, answer the why.
  2. Come up with several different possible scenarios, and imagine yourself living through them. Sometimes we focus so much on getting through the door we don’t stop and wonder what it will actually be like to live on the other side of the door. And we wonder why we are so shell-shocked when we get there.
  3. Consider the best and worst scenarios equally. It’s easy to get really excited about all the positives, or really hung up on all the negatives. Take a step back and make sure you consider both objectively and equally. If you’ve been spending a lot of time thinking about one side, encourage yourself to switch. Be fair.
  4. Go beyond your idea of the options and find ways to approximate what each option will really be like.
  5. Do your due diligence but don’t overthink it. A solid due diligence is one that is comprehensive and specific, which means your research was broad, and you looked beyond the surface of all important issues. Mistakes I’ve made (and seen other people make) include overthinking on one area or issue and completely missing other critical issues. Hopefully the points mentioned above can help with broadening the scope of the due diligence and avoid getting hung up on any specific issue.

III. Don’t let fear taint your decision

  1. Identify your fears. Know the difference between being careful and being chicken. Recognize when you are being productive and moving towards a well thought-out decision and when you are paralyzed by indecision and sinking into confusion.
  2. Distinguish between deal breakers and excuses. People will do a lot to avoid owning their fears and admitting they are terrified, including making all kinds of excuses. These excuses might move you towards the “safer” option, but that’s not always the right option. Don’t let excuses confound you and undo all the work you did in (I) and (II).
  3. Finally, rise above your fears by:
  • Embracing uncertainty. Risks and opportunities are two sides of the same coin. Uncertainty is not good or bad; it’s an unavoidable part of life. The sooner you learn to embrace this fact of life the better.
  • Letting go of perfection and stop letting mistakes threaten your identity. Perfection is an illusion that gives too much weight to things we can’t control (the outcome) and not enough credit to what we can control (the process). Focus on doing the right thing every step of the way, and have faith that things will work out eventually (though probably not how you imagined it). Success is not final, failure is not fatal: it is the courage to continue that counts. I don’t know if Churchill really said that, but it makes a lot of sense to me. Don’t let the fear of failure stop you from moving forward.
  • Having confidence in yourself. You’ve gotten this far and that means you did a lot of things right. Trust yourself and the process, and accept there will surprises, both good and bad, no matter what you choose. As long as you are alive, there is always the chance to make it alright.

Most people I know already do a pretty good job at (II), but don’t spend enough time on (I) or (III). The ordering of the three steps was absolutely intentional. I think we often focus too much on the options and not enough on ourselves. When it comes to personal decisions, we are both the decision maker and the one that is most directly impacted by our decisions (versus making decisions for others, e.g. making decisions in a company or as a parent). It should be obvious that understanding who we are, who we want to be, what values and objectives are should be paramount.

I find it ironic that people focus so much on the uncertainties and risks (e.g. will she like me? Will I get the offer? Will it work out?) and lament the lack of perfect information, while failing to properly examine themselves (e.g. do you really like her? Why do you want the offer? What happens after you get in? What if it works out?). Developing self-awareness is actually critical to making hard decisions, and it doesn’t involve wrestling with uncertainties and risks. You have more access and control over yourself than anything else, and properly understanding who you are and what you truly want is just as important (if not more so) than trying to assess the risk of everything else. I wrote the three steps so that they begin and end with ourselves, because that is both the most constant and critical part of the equation, and also what is most often missed.

One Comment

  1. […] In the world of romantic relationships, you need love and work. And in the world of professional endeavors, you need grit, the combination of passion and perseverance. But here’s the thing: you can’t make it work with everyone no matter how hard you try (or how much you love them), and you can’t get gritty no matter how much you persevere if you are not truly passionate about what you are pursuing. The hard part is most of us will end up in one or more of those relationships with someone we really like, or even love, but with whom we just can’t make it work. But we tell ourselves that because we love them (and they love us back), we should stick it out and keep trying. Similarly, many of us have had jobs, or even careers that are interesting, pay well, and look good on the resume, but perhaps still leave us wondering if that’s all there is to work life. These are the hard cases because the people and the jobs offer a lot: love, status, security, etc. They are not trivial by any means, and that’s why it can be so hard to walk away. But if you’re not really happy, with the relationship or the job, are you staying because you truly believe this is the best option for you or are you staying out of the fear there is nothing better? If you have been unsatisfied with how things are, do you have convincing evidence that it will improve, or are you resigning yourself to settling for less than what you want and deserve? I’m not not advocating for quitting when things get hard or walking away prematurely; but it’s important to know the difference between persevering through challenges versus settling out of fear, because fear never resulted in good decisions. […]



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