Three Versions of Your Future (And Why You Need All of Them)

Read this on victoriaprew.com​

Read time: 2.5 minutes

Hey team!

I've been thinking about the concept of portfolio careers for a while now. Most people pick one career path and hope for the best.

Here's what happens to (almost all of us): we pick a path at 18, 22, 25. Some career counselling at school or parental advice. We commit. We specialise. And then we spend the next decade wondering "what if?"

We feel trapped because we think there's only one version of ourselves that's "right."

I've always shied away from the traditional "Five Year Plan", even though I'm a real planner. Why? Because it feels formulaic. Career limiting. It's also not the reality of the world we currently live in.

Enter: Stanford's Life Design Lab who proved something different.

There's more than one you.

[the system]

The Odyssey Plan

Stanford's Life Design Lab created the Odyssey Plan, developed by the same minds behind the bestselling book Designing Your Life by Bill Burnett and Dave Evans. It's incredibly simple.

You imagine 3 completely different versions of your next 5 years.

Here's how it works:

Path 1: Your Current Trajectory​
This is what you're doing now. If nothing changed, where would you be in five years? This is the path you tell people about when they ask what you're up to. Same job. Same routine. Same direction.

Path 2: Your Alternative​
What if Path 1 disappeared tomorrow? You got made redundant. The company shut down. Or you woke up and realised you couldn't do this any more. What would you do instead? What if you took a risk? Switched careers? Moved to a new place?

Path 3: Your Wild Card​
If money wasn't a factor. If social expectations didn't exist. If no one was watching and you didn't have to explain yourself to anyone. What would you actually do?

[the framework]

For each path, you need to get specific:

• What are the top three things you'd love to do more of, and three things you never want to do again?
• What does a typical week look like?
• Who are you spending time with?
• What are you proud of?

The key: make them genuinely different. Not "project manager at this company vs project manager at a bigger company."

Make one of them wild. Make one of them scare you.

After you've visualised each path (drawing helps activate your creativity in a different way), assign each a title and assess how you really feel about what you put down on paper. For each plan, consider:

• Resources – Do you have what you need?
• Confidence – How sure are you about this path?
• Coherence – Does it align with your values?
• Likeability – Do you actually want this?

Sometimes we brainstorm and realise we didn't get what we wanted, but embrace the prototype mentality. Do another!

[the lesson]

The biggest trap in life? Thinking your current path is the only path.

It's not a bad thing to take a step back and admit you feel a little trapped by a career decision you made years ago.

Most people live on autopilot. The Odyssey Plan forces you to zoom out, ask bigger questions, and imagine other routes. I'm a big believer in living your life intentionally, also having half an eye on the way the world is changing in 2026 and beyond.

I found Odyssey Planning a pretty cool way of projecting into the future and a valuable activity for presenting ourselves with possible options and seeing what our intuition feels is right (or wrong). Time and time again, participants from Stanford's workshops cite this as the most transformative career tool.

Once you've created your Odyssey Plans, take steps to prototype them:

• Talk to People Living That Life (Quick chats with people who have pursued similar paths). Or ask AI to break down their "career blueprint".
• Try Small Experiments (Shadow someone, take a free class online, or start a side project to test your interest)
• Reflect and Iterate (Which plan excites you most? Which aligns best with your values?

So here's your homework: map out three versions of yourself.

Your current path. Your alternative. Your wild card.

Then ask yourself: which one am I actually building towards? And is that the one I want?

The Odyssey Plan shows you there are many right choices. You don't have to pick one and commit forever. You're allowed to experiment. You're allowed to change your mind.

See you next Monday!

Victoria