Have you ever tried to see the future? Like *really* tried?

Sometimes I do. I try really hard to put myself in some future moment and just be there.

Not even like visualizing some distant time 50 years from now. I mean literally picking a moment a few minutes from now and trying to really see it.

Sometimes I do this in the morning while I’m getting ready. I’ll be in the shower and try to guess exactly what it’ll feel like 15-minutes later when I’m walking to the coffee shop. Or last week, I was back in my hometown driving the road I took to school every day as a kid - I kept trying to guess exactly what I’d experience a mile down the road but just couldn’t see it.

No matter how familiar or close in time the moment, it’s always impossible to see. By the time it’s come and gone I’ve already forgotten what my imagination of it felt like in the first place. It’s so hard. Like looking out through a fog at night.

It turns out this is because the world is stochastic.

By this I mean real-world outcomes are randomly determined according to patterns and probability distributions. You can’t see the future, because outcomes aren’t deterministic. Time only moves in one direction (at least that’s the only way we can see it). Even things that feel guaranteed - Old Faithful, the Sun rising, Warren Buffett 20% annualized returns - follow a probability distribution.

I learned about “stochasticism” about 6 years ago in a college stats class. The word stochastic traces its origin back to the Greek word “stókhos” which literally means “guess”. That’s kind of beautiful to me - even the ancient Greeks with all their elaborate beliefs about the divine saw the future as more or less a guessing game.

And as I think about it recently, it’s actually quite freeing to accept a stochastic reality. To accept that can never ever know what will happen next. No matter how hard you try to peer into the future, no matter how confident or close, you just. can’t. ever. know.

So what can you do? There are pretty much three things: 1) You can hope, 2) You can pray, and 3) You can embrace probability. Most of us have a decent grasp on the first two so allow me focus on the 3rd for now:

The Stochastic Worldview

As I would imagine a wise man like Confucius probably once said: in a probabilistic world your best bet is to chronically put yourself in good position and hope for the best. Luck favors the prepared, fortune favors the bold.

But what does "putting yourself in a good position" actually look like in practice? After thinking about it for a bit, here’s a few tips and tactics that help me:

1. Think of life in “Bets”

It’s easy to think of the world and decisions as binary outcomes: success or failure, right or wrong, yes or no. But the real world is a spectrum of probabilities.

Generally, major life decisions aren’t about finding the "right" answer. It’s about making smart bets with incomplete information When I left consulting to start Uptrends, I wasn’t certain it would succeed. But I did recognize that starting my own business was a positive expected value bet: high upside potential with a downside I could live with.

A career isn't a single chess move; I’d say it's more like playing poker. You're making a series of bets with imperfect information; even the best decisions can lead to bad outcomes due to randomness. The goal isn't to never lose - it's to make decisions where the odds are tilted in your favor over time. That’s called leverage baby.

2. Create Optionality, Not Plans

The typical advice is to "have a plan." My mom loves to say that. But rigid plans break against offset flexibility, and in a probabilistic world, flexibility is critical. Flexibility in the realm of decision making means “optionality”, leaving your options open for unexpected opportunities. Do this by:

• Building transferable skills that work across multiple domains (writing, public speaking, data analysis, relationship building)

• Expanding your network outside your immediate circle or industry

• Maintaining financial flexibility so you can take advantage of opportunities when they appear

• Cultivating diverse interests that might unexpectedly connect in valuable ways

I've seen this play out in my own career. When we had to pivot Uptrends, I realized it was the skills and connections I'd built "on the side" that ended up being most valuable - not the specific knowledge of building a stock market news monitoring app that I’d been so focused on.

3. Use Probabilities in Daily Decisions

You don't need a statistics degree to think probabilistically. Don’t underestimate yourself. Here are some practical ways to apply this mindset:

Ask "then what?" — When faced with a decision, don't just think about the immediate outcome, play out the chain of reactions. If I take this job, and then it doesn't work out, and then the industry shrinks, where does that leave me? If I launch a newsletter or podcast, then 4 weeks in realize I don’t actually have time to maintain it, where does that leave me?

Consider the base rates — Whatever you're trying to do, look at how often people in similar situations succeed. If 90% of startups fail, that doesn't mean you shouldn't start one. It means you should be realistic about the odds and plan accordingly. This can mean finding ways to increase your odds and recalibrating - ex: joining a startup accelerator, bringing on some killer advisors, picking a good industry and/or biz model.

Don't confuse decisions with outcomes — Sometimes good decisions lead to bad outcomes, that is the nature of randomness. Don't beat yourself up when this happens, and don't change your decision-making process based on a single data point. You are looking for trends amongst the data points. Again it’s like poker.

4. Maximize Your Surface Area for Luck

Luck isn't mystical, it's mathematical :-) The more opportunities you expose yourself to, the more likely you are to get lucky. This means:

• Shots on goal — Apply for jobs that seem out of reach, reach out to people you admire, submit your work for opportunities. I believe the 2nd leading goal scorer in NHL history Wayne Gretzky had a famous saying about this, not sure..

• Saying YES — Attend events outside your comfort zone, travel to new places, try new hobbies. It can be scary. I like to remind myself the 90% of the time when I’m worried about getting out of my comfort zone I end up having a good time and growing. No growth in the comfort zone !

• Sharing your work publicly — The blog post, side project, or tweet that changes your life won't reach anyone if you keep it to yourself. Build forcing functions to share yourself with the world. Write a blog, host LinkedIn Lives, put on indusry-specific pickleball events. You really can just do shit no one is stopping you (but you)

5. Embrace the Regret Minimization Framework

When facing tough choices, ask yourself: "When I'm 80, which choice will I regret not taking?" This powerful mental model cuts through the noise and focuses you on what really matters. I wrote more about that here.

It's not about avoiding regret (impossible). When choosing between two big things, it’s about minimizing the regrets that would haunt you the most. For me, that meant starting a business instead of staying in my safe, cushiony, salaried(!) consulting job.

Even if it failed (which parts of it did), I knew I'd regret not trying far more than I'd regret trying and failing. A step further — ask yourself “whats the worst that could happen??” for me the worst case starting my own business was failing and learning A LOT from it (the ‘real-world MBA’ as Elon says)

6. Build Anti-Fragile Systems

In a random world, the goal isn't just to survive uncertainty — it's to build systems that actually get stronger from volatility. Nassim Taleb talks about this in his books, calling it "antifragility." For you this might mean:

• Diversifying your income streams so you're not dependent on a single job (I have 2 income streams, my startup, and teaching startup classes)

• Building a reputation that transcends any particular role or company. It’s never too early to start a personal brand. Just takes a few blog posts and LinkedIn posts per month :-)

• Cultivating skills that become more valuable in times of change (crisis management, adaptability, creative problem-solving) - call these ‘fine wine’ skills

• Maintaining low fixed costs so you can weather downturns and take advantage of opportunities. Only spend when you HAVE to.

I think the beauty of embracing stochasticism isn't just that it makes you more successful, it makes you happier, too. When you stop expecting certainty from an inherently uncertain world, you release a major source of anxiety. You stop beating yourself up for not predicting the unpredictable.

Instead of trying to see through the fog, you learn to navigate within it. You accept that sometimes you'll get lucky, sometimes you won't, but you can always position yourself to capture more upside than downside from life's inherent randomness.

In a world where even tomorrow's weather isn't guaranteed, that's about as close to seeing the future as any of us can get.

Peace,
Ramsey