My Favorite Questions for Making Tough Decisions

Sometime you’ll encounter tough decisions that can leave you wallowing in indecision, such as whether to change jobs or careers, end a relationship, move to a new city, or pursue a new lifestyle direction. There are many processes you can use to make intelligent decisions, but all of them have shortcomings when you’re dealing with imperfect information. Sometimes all it takes to gain sufficient clarity though is to ask the right questions. A good question can shift your perspective about your decision and make the wise path obvious.

When I face tough decisions, here are some of my favorite questions to ask:

Will this help me grow?

Since growth is one of my highest personal values, I favor decisions where I can expect to learn and growth. If I see little or no growth on a particular path, I’ll tend to lean against it.

This heuristic gives me a bias to embrace the new, as opposed to repeating something I’ve already done. It’s one reason I usually don’t repeat workshops. Even though it’s more work, I favor doing new workshops because a new workshop pushes me to learn and grow a lot more than repeating a past workshop does.

Asking this question helped me join Toastmasters in 2004, and I remained a member until 2010. I felt a bit anxious about getting involved with the group since I didn’t think it would be a comfortable experience to practice public speaking. But I went to my first meeting and joined a club because I figured that it would be a growth experience, and it certainly was. When the growth aspect faded and the experience became overly familiar, I quit Toastmasters and shifted my attention elsewhere.

There are many situations where fear and hesitation might hold me back, and then my mind wanders towards justification. I can’t because I’m too busy. The timing isn’t right. I’m not feeling my best. Yes… but will it be a growth experience? If a decision will help me grow, then I’m inclined to lean into it.

Sometimes my answer to this question takes the form of a grudging dammit, yes. Part of me doesn’t want it to be a yes, especially when the decision involves facing a fear, a lack of skill, or a lot of extra work, but it’s a good step to at least admit that if I move forward and say yes, I know it will be a growth experience.

Would my best self do this?

Asking this question gave me clarity when I was trying to decide whether or not to uncopyright all my blog posts back in 2010. I had created a tremendous body of intellectual property, and I owned it 100%. But I often wondered what would happen if I let go of that ownership and donated it to the public domain. It seemed like a huge leap, and there was no good way to predict the outcome.

When I asked if my best self would do this, the answer was clear. If uncopyrighting my work would help more people than keeping it copyrighted, my best self would pull the trigger and do it.

My best self is brave, generous, and creative. He could handle the consequences of giving so much away and letting the world run with it. He trusts that it would work out. He knows he can always create more. He doesn’t want to depend on ownership of intellectual property for his sense of security. For him it’s enough to feel secure in who he is. Even if things didn’t turn out so well, he could handle that too. He’s strong enough to deal with the consequences.

Asking this question removed enough doubt to make it so. Would my best self do this? Of course he would.

This still wasn’t an easy decision, but at least I knew that if I could do it, it would bring me further into alignment with my best self. If I held back, I’d be keeping myself out of alignment with him.

Do I want the memory?

Every decision ultimately becomes a memory, and the sum of your decisions will eventually become a string of memories. So which memories do you want?

Do you want the memories of maintaining your current social media habits for the next 10 years? (It’s extremely rare to find someone who can honestly answer yes to this.)

Do you want the memories of keeping your current job for another year? What about your current relationship situation?

Do you want the memories of taking that trip, or would you rather have the memories of not taking it?

This is a really powerful question, and some people have gained immediate clarity the first time they’ve asked it.

Of all the social media interactions and online commentary you’ve posted over the past decade, what do you remember? I remember very little of it. It’s all just a blur. My mind seems to value those memories so little that it didn’t store them in any meaningful detail.

This question helped me lean into lots of delightful travel experiences. Every year I travel to places that I’ve never been before, and one reason is that I love acquiring the memories that come from travel.

When you look back upon the past year, what do you remember? Do you like those memories? Could you have created better memories?

When I think about the past year, I remember eating lots of yummy meals at this small restaurant called Verde Vegan in Acapulco. I remember walking around the streets of London in the rain. I remember going to the top of a volcano, visiting a coffee plantation, and seeing several waterfalls in a rainforest in Costa Rica. I remember sipping espresso on a cobblestone sidewalk in Italy, walking around Villa Borghese park, staring up at the ceiling of the Sistine Chapel, and taking silly photos at the Mouth of Truth. I remember lots of fun times while spending 30 days at Disneyland. I remember seeing many plays at the Fringe Festival in Winnipeg and eating samosas with tamarind sauce. I remember sharing laughs and insights at last year’s workshops and going out to dinner with the attendees afterwards. And I remember doing all of these things with my girlfriend.

Most of my best memories are not about working at my desk. They come from having interesting experiences. Is it the same for you?

I’ve taken action on a lot of stretch ideas – and sometimes just plain silly ones – after asking myself if I wanted the memory. One of the silliest was last year’s decision to spend 30 days in a row going to Disneyland. That’s a lot of time to spend on such an experience, and I certainly could have used that time in other ways, but I realized if that I did it, I’d end up with some wonderful memories, plus the overall memory of taking action on a stretch experience.

I rarely regret taking action in a new direction.Usually I regret holding back. I think that’s true of most people. We tend to regret the opportunities we missed as opposed to those we pursued, even if we didn’t get the results we hoped for. We regret not trying even more than trying and failing. Failing is okay. Not trying just sucks.

You could ask yourself which path you’re more likely to regret, but regret is just one type of memory. So when you ask this memory question, it already covers potential regret.

How will this sculpt my character as a man?

I’m sharing this question the way I ask it, so feel free to modify it to fit your gender, or use a gender-neutral substitute like, How will this sculpt my character as a human being?

This was an especially powerful question to ask when I was in my 20s, and I was thinking about what kind of man I wanted to become. This question stemmed from a realization I had while sitting in jail for a few days when I was 19 years old. I saw myself becoming someone much darker than I wanted to be, and that realization woke me up. I realized that in order to change the man I was becoming, I had to start making different decisions.

The decisions you make ultimately define your character and personality. Making a decision is like chiseling out the sculpture of who you’re becoming. Most decisions only chisel out small details. Some decisions define significant aspects of the final piece. The decisions I made while sitting in jail were some of my life’s biggest.

If you’d visited my website between 2004 and 2008, you would have seen a lot of ads. At the peak I was earning $12-13K per month in passive income from having advertising on the site. In late 2008 though, I removed all the ads, which immediately shut off that income.

One reason I made this choice is that I saw it as a character decision. I didn’t feel congruent with distracting my readers with third-party advertising when they came to my website to read about personal growth. I faced a choice, and each option would sculpt my character differently.

The first option was to continue enjoying the easy passive income from advertising for many more years. By today it would probably have been about a million dollars extra if I’d kept having advertising. This would also mean many years of sculpting myself into a man who accepts a misalignment with his values in order to make money, which would only make it more likely that I’d continue making similar decisions down the road.

The second option was to remove the ads and look for more aligned ways to earn income. This would mean pursuing a path of greater congruence, even if it might be less profitable. It would also be a harder path to take because the advertising income was very easy to maintain. This path would definitely be more work.

I chose the second path because I believed it would sculpt my character in a more positive direction. It would be more difficult in the short term, but I liked the idea of shedding misaligned income sources in order to do the harder work of creating aligned sources. The year after I made this decision, I created and delivered my first three-day workshop. Fast forward to today, and now I’ve done 16 of them. While the workshops weren’t as lucrative as I expect the ads would have been, they’ve paid off in many other ways that I value much more than money. For instance, I met my girlfriend Rachelle at that first workshop, and a key strength of our relationship has been our values alignment, such as the fact that we’re both long-term vegans. And we love traveling and having fun lifestyle adventures together as well.

If you accept a misalignment in your life, you’ll attract more of the same. If you go for congruence, you’ll also attract more of the same. So think carefully about how each decision will sculpt your character.

I’m glad that I made the decision to remove those ads in 2008. Getting that incongruence out of the way helped me feel much closer and more connected with my readers. Since then I have met – and hugged – hundreds of them in person. The ads didn’t feel heart-aligned, so by getting those out of the way, I removed a barrier that might have otherwise weakened this relationship.

I could name many more instances where this character question has helped me make tricky decisions. This question nudges me to face more fears, to pursue new experiences, and to delve deeper into personal growth explorations than I otherwise would. I don’t always get it right, but I get it right more often when I ask this question.

Could I reverse or undo this decision?

Last week I decided to get a new home office chair to replace my really old beat up one. As I began browsing online, I thought that maybe I should get a really nice one this time instead of just another cheap sub-$100 chair from Office Depot, especially since one of my health goals for this year is to work on improving my posture. After doing some research, I narrowed the decision down to two choices: the Herman Miller Embody and the Steelcase Gesture. I’ve never owned a chair that had a name before.

Both chairs costs more than $1000. Both have radically different designs. I couldn’t find any stores in Vegas that actually carry them, so I couldn’t try them out first. Online reviews were helpful, but I could find really detailed, in-depth reviews that ranked either chair above the other. And wherever one chair got lots of four- and five-star reviews, I could always find other people rating it one and two stars. It seemed to come down to a matter of personal preference.

Instead of wallowing in indecision or not getting a chair at all, I went with the one I expected to like best – the Steelcase Gesture – even though I had to order it sight unseen and hope for the best when it arrives. What helped was knowing that the decision is reversible. If I don’t like it, I can pack it back up and return it. Or worst case I can always sell it. I might waste some time and money if I made a bad decision, but the long-term consequence is minimal, and the damage is largely reversible.

Some decisions are permanent, and you can’t simply undo them. If you quit your job or leave your relationship, you may not be able to go back if you later change your mind. But for many decisions, there’s a built-in undo. You can often return items you purchased. You can move back to your old city. You can buy back similar possessions to replace those you gave away. You can switch back to your old diet and exercise routines.

If a decision is reversible and/or the negative consequences of a mistake are low, then I’ll tend to lean towards the new experience. At the very least, I might learn something from it.

Can I test this decision?

If you can’t undo a decision, maybe you can test it somehow. Could you dip your toes into each path to gain more clarity about the options? Could you collect some real world experience before you have to commit?

This mindset was especially helpful in 2009 when trying to figure out whether Erin and I should stay together. By entering a polyamorous phase for several months, it was possible to test the waters by exploring other connections without ending the marriage. That provided tremendous clarity that the grass would indeed be greener on the other side. It still wasn’t an easy decision, but it became easier by testing.

Some long-term couples go through a trial separation first in order to test what their lives might be like if they were to separate and divorce. A good book for structuring such an arrangement is Should I Stay or Go? : How Controlled Separation Can Save Your Marriage. That book takes a pretty formal approach, which Erin and I didn’t really follow, but the general idea of testing the waters first is certainly helpful in these types of situations.

Testing a decision can help you tip one way or the other, so you don’t remain endlessly stuck in ambivalence, where you’re constantly waffling about which direction to go.

* * *

Try asking some or all of these questions the next time you face a tricky decision. I think you’ll find them useful tools for increasing clarity and making better choices. When I’ve shared some of these questions with other people, their number one favorite is usually the memory one, so that may be a good one to start with.

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