How To Make Decisions In Uncertain Times - Three MUST-ASK Questions
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Most people think they make consequential decisions rationally, by weighing pros and cons, imagining outcomes, or asking others for advice. But the research shows that’s only part of the story. In reality, how people make big decisions (about relationships, career, money, moving, etc.) is far more complex, and often irrational in predictable ways.
Most consequential decisions are emotionally-driven, and if you’ve been reading Life Intelligence for a while, you know about the strange ways emotions pull our strings and not always in our best interest. We find ourselves leaving jobs, affiliating ourselves politically, or leaving a partner because of how we feel, not because of a spreadsheet or a thoroughly thought-out strategy. More reactive than proactive and more emotional than rational.
Frequently, emotion colors the “facts” we select to support the story we already prefer. We later rationalize with logic to feel better about what was often a gut call.
Under stress and facing complexities, we use mental shortcuts and fall victim to their biases. It takes effort to untangle the mental spaghetti, but it takes more out of you to live with the consequences of poor decisions.
Decision-making is one of my favorite subjects to write about. Feel free to check out Untangling Your Mind, Stop Confusing Yourself. We are in week #3 of the Life Transitions series, and last Wednesday, I wrote Emotional Weather, which looks at how we deal with uncertainty and how we can do better.
So, here I go again, but this time, I am giving you three questions to ask yourself when you must make a decision without shooting yourself in the foot. (With a bonus fourth at the end.)
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So, here we go, the four super helpful and highly consequential questions to ask yourself in times of complexity and uncertainty… which is now, but also every time your life explodes in ways that scare and challenge you.
For a species having a hard time staying in the moment, humans sure like to make their decisions as if the moment is the only thing that matters. We will do almost anything to immediately relieve the tension and discomfort caused by the conundrums we find ourselves in. Sadly, our knee-jerk reactions sometimes lead to dire consequences and often take us further away from our goals and dreams.
So the first question we should all be asking ourselves when facing a fork in the road is:
“What decision I make now will still make sense a year from now? Three years from now?”
This question pushes you to zoom out. It moves you from reacting in the moment to thinking strategically. The time-horizon shift helps override the emotional noise and brings clarity around long-term alignment.
It prevents impulsive choices based on fear, comfort, or temporary pressure. It clarifies what actually matters to you, not just what feels good now.
A decision that makes sense long-term is likely to be sustainable, financially, emotionally, and relationally. For example, taking a high-paying but soul-sucking job now might look good this month, but will it make sense later? How would you feel about your decision when burnout hits in 18 months? Saying yes to a relationship because it feels secure now and relieves your loneliness in the moment, even though you see the red flags in the person, will that still feel right when you can no longer ignore these red flags a couple of years in, because they impact the quality of your life?
This question encourages you to consider the future version of yourself, not just the present one. I am big on considering my future self. I’ve accepted full responsibility for my future self and treat it like a real person, not a hypothetical one. I owe it honesty, integrity, and loyalty. And I make sure I don’t do anything that would jeopardize my future self’s well-being, quality of life, and prospects for the future.
Research shows we often see our future selves almost like strangers. The disconnect causes procrastination, overcommitting, poor savings, or staying in stuck patterns, lame relationships, and dead-end jobs. But, if you can think of your future self as you think of your kid’s future and treat yourself accordingly, how would that change things?
Would you let yourself eat junk food now? What advice would you give yourself about your chosen relationship from the perspective of your future self? How would you like your future self to look and feel 5, 10, 20 years down the road, and how are you supporting or not supporting this?
We all say we value growth, freedom, or stability, but to test what this really means, you need to ask this question. It might reveal that you prioritize certainty now over expansion later. Or that you're tolerating something short-term that actually chips away at your core values and stated goals.
Before I left California last year, I asked myself this question. From the perspective of the moment, I worried, “What if I miss my friends? What if I hate it? What if this is a giant mistake? I’ve worked so hard to get to where I am. What if I lose it all?” From the perspective of my future self: “Am I glad I tried this?”
I imagined my future self, the me living in 2025/6/7. She’s wiser, a little more weathered, definitely more self-assured. She’s already walked the path I was standing at the edge of. From where she sat, looking back, she gently leaned in and asked me:
“Will staying in California make sense to you three years from now? Or will moving to Europe have been the chapter that set something bigger in motion?"
"What will you wish you'd given yourself permission to explore?"
"Will you regret trying Europe and realizing it wasn’t the right long-term fit… or regret never having given it a real shot because fear or comfort kept you small?"
"What rhythms of life do you imagine yourself craving three years from now—pace, cost, connection, meaning? Which place makes those more likely?"
"When you picture your 2027 self sitting in a cozy apartment or walking a familiar street, where is she? What’s around her? What does her day feel like? Are you in alignment with that version of you, or avoiding her?"
Sometimes, the most grounded guidance comes from imagining the person we’re becoming, not the person we’re trying to preserve.
So, when you sit with your future self, what do you hear yourself saying? And more importantly, what will your future self thank you for?
Naturally, the second major question to ask in time of uncertainty is related to the first.
“If a year (or two, or three) from now your decision was used as an example of what you did right to transform your life in all the amazing ways you wanted, what would it teach?
That question is like a reverse eulogy meets visualization meets future wisdom drop, and it’s very powerful, especially during big life pivots. It shifts you from a fear-based, reactive mode to a growth-oriented mindset. It asks, “What if this is the thing that changes everything for the better?”
Suddenly, your brain starts tracking for hope, strategy, alignment, not just risk and loss avoidance. It opens new internal pathways. It’s not just imagining success, it’s rehearsing wisdom. You become the intentional author of your story. You're saying: “This decision will become part of the story I tell about how I got here.”
Your decision becomes a sacred act of choosing what kind of transformation you’re willing to let into your life. By imagining how it might work out and what you’d learn, you can start behaving in alignment with that version of yourself today. It’s like retroactively borrowing confidence from a future where you already succeeded.
For me, the lessons I was aiming to learn from my decision in the future were:
“Trusting my inner voice opened doors I couldn’t yet see, to positive experience I didn’t know existed yet.”
“I learned that designing a life around what fuels me changes how I do things.”
“Courage compounds.”
“I learned that choosing myself, my rhythm, my joy, my values, is always the better choice.”
“I learned I’m more adaptable and creative than I gave myself credit for.”
“I proved to myself that freedom and stability aren’t opposites, they’re a design problem I figured out.”
“I discovered a way of living that didn’t just look good on paper, but felt deeply right in my body.”
Again, naturally, the third question arises from the first two:
“What is the cost of waiting?”
This deceptively simple but wildly clarifying question cuts through noise, fear, and indecision like a laser. When stuck or delaying, we usually focus on the risks of acting. But rarely do we consider the hidden risks of not acting, such as emotional wear and tear, missed opportunities, delayed growth or healing, financial stagnation, and the slow drip of regret. So, this question flips the script: “Sure, taking action has a cost. But what’s the price of not taking it?”
And sometimes, that price is quietly huge. Waiting feels safe because it mimics control. But not deciding is deciding. Delaying often equals choosing the status quo by default, which may not be what you really want.
When you freeze in place, you often lose connection to your deeper purpose. This question forces a reset. Ask yourself, what are you trying to protect by waiting? What are you giving up in the process? What version of your life are you postponing?
Before deciding to upend my life the way I knew it, I realized that I was delaying finding out what’s actually possible. I might miss a year of lower living costs, creative freedom, new relationships, or business experiments that could compound, plus a ton of adventure and checking things off my bucket list. My emotional resilience may slowly erode under the weight of “not-quite-right” circumstances.
Meanwhile, my future self was whispering: “I could be building something real by now and be a totally different person.”
Interestingly, a year later, the most frequent comment I get from people who see me now is, “You’re so different now.” They tell me I am more relaxed and patient. I connect better. I am warmer. I can kind of see it…
The bonus question to ask yourself requires you to look at your circumstances realistically, not with hope. You need to ask yourself:
“What if this isn’t the weather? What if this is climate change?”
When in the thick of things, we try to remain positive and hope that tomorrow, when we wake up, things will have changed on their own. Your partner will decide to stop drinking or putting you down. Your boss will appreciate you. Your retirement account will swell magically on its own.
Asking this question is like putting on X-ray vision goggles for your life. It’s a question that takes you from temporary coping to truth-telling.
What if you are not just having a bad week, stressful month, a tough conversation, or a bump on the road? What if you are actually in a job that chronically depletes you, a relationship that never feels safe, a lifestyle that taxes your well-being irreparably?
We are masters at explaining away discomfort and rationalizing the choice of not doing anything about it. But if we are to tell the truth, we may have to admit that we exist in a pattern, in a paradigm, not just having an off week. We may have to admit that what we’ve been calling a rough patch is actually the baseline.
Choosing honesty gives you agency. It forces you to assess the system, not just the symptoms. Instead of wondering how to fix this moment, you want to ask yourself if the whole system is broken. Whether it’s your schedule, career path, romantic dynamic, or physical environment, this question helps you step back and reflect on whether you are putting out spot fires in a forest that’s already burning down.
If you're resilient, self-aware, or even just hopeful, you may keep managing things that shouldn’t be managed anymore. Asking yourself this question will help you see if you are fully relying on your coping mechanisms and invites you to stop normalizing the intolerable.
It gives you permission to pivot. You stop waiting and start redesigning.
Let’s say you’ve been feeling chronically uninspired in your work. You tell yourself, “It’s just a slow season. I’ll feel better when summer starts / when the project ends / when I get a raise.”
But if you ask: “What if this isn’t weather? What if it’s climate change?”
…you might realize that you've been uninspired for years. Your values have evolved, but your work hasn’t. You're building a life that no longer reflects who you’ve become.
And suddenly, it’s not about surviving the next month.
It’s about reimagining the next chapter.
I am curious, what will you take from this post? What seems relevant to you in this stage of your life?
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Much appreciated. Wishing all of you a wonderful life, wherever you are.
V and Lulu B.