Wayfinding Your Future and Prototyping Life Changes

Post-pandemic it’s been interesting seeing what people did with two years of lockdown reflection. I wrote earlier about hoping to see more people starting businesses, making science, creating art, and doing not-for-profits.

β€œThe highest treason a crab can commit is to make a leap for the rim of the bucket.”
― Steven Pressfield, The War of Art

While disappointed seeing people run right back to jobs they swore they’d leave, I’m also shocked at people making wild, ill-considered leaps to “follow their passions” without planning or contingency.

Amongst friends, I’m known for re-inventing myself every few years. So, many people making changes (or not, but wanting to) asked me for advice on life changes. So, I wanted to share what’s worked for me and actionable advice in the vein of my financial independence posts.

My TLDR advice to you is:

Product manage your life

Also, the one thing you can do to unambiguously improve life outcomes: Run Experiments.

You’ll be “luckier”, move away from things making you unhappy, and edge towards the things that may make you happy.

Product Managing Your Life

You want to make changes. I get it. Life should be more. You don’t want to bob like a cork on the ocean waiting for wind and tide to take you somewhere. You want to swim.

So, what do I mean by by product managing your life? Treat your life as a set of inter-related features you are continually trying to incrementally improve (and measuring how they are improving or not.) over time. Explicitly. Methodically. Measurably.

People are abysmal at knowing what will make them happy in the future (sidebar: Great, free Yale course on being happier Backed by science. Recommended.). To say nothing of planning for that future. We’re great at recognizing when we’re unhappy, but less great at the other thing.

To fix that, it realy comes down to two key disciplines:

  1. Roadmap
  2. Prototype


Why Roadmap? Everyone needs a strategy. And a strategy to simplify it (ripping off the great Richard Rumeldt ) consists of a future state (B), a realistic assessment of your current state (A), and a actionable plan and set of actions to get you from A to B.

Roadmapping is a process to help with this. Easy process. Hard thinking.

Few people spend enough time really thinking about their future, and major life decisions such as where to live, where to work, and who to partner with get short shrift in consideration. Even fewer spend enough time coming up with a legit concrete plan (and contingencies) for how they are going to accomplish that state if they have thought hard about it. Yes, it’s hard, but having a plan, and one that’s adaptable, is key to you getting to within spitting distance of what you think you want. Aim for something both aspirational and actionable: a five year plan .

The first problem most people have in wayfinding their future is the simple fact that there are a ridiculous number of path and choices open to most people (at least those most likely reading this post). The second, is simply a failure of imagination since we lack models of other possible life paths so use societal defaults like “get a job” which are comfortable, non-controversial, but avoid the hard job of thining about whether that actually makes sense for your circumstances.

How do you crack this issue? My favourite is alternate timeline future casting I described as the “Alternative Destiny Daryl” technique in the Career Progression and Discovery Framework we minted at my last two companies. Basically, there are probably many, many interesting things you could be doing with your life and it is hard, gazing into the misty future, what your best future self might be.

How does it work?

As a great technique to unblock this, Stanford Life Design Labs came up with the technique of 5 Year Odyssey Planning .

To over-simplify: take 3 sheets of A4/8.5x11 paper in landscape mode. Draw 4 vertical lines to separate the three pages into 5 regions each which represent each year of your 5 years. This is your visual and graphical timeline. For each of your timelines it should include other life events than merely work: children, marriage, sabbatical, academics, industry or career changes, creative endeavours, and rest should all be accounted for in your big picture.

Your page(s) should also have:

  1. Headline title
    at top that describes this future (SLDL suggests 6 words)
  2. Questions
    raised by these timelines to test assumptions
  3. Dashboard
    at the bottom where you can gauge the alternatives in resources, likability, confidence, and coherence (I score mine on a scale from 1 => 5 for each category)

As starting points to imagining your 5 Year Plans, the SLDLs recommends in Designing Your Life taking on three approaches if you’re stuck on how to start.

  1. That Thing You’re Already Doing
    current life lived forward or idea you’ve been nursing
  2. The Other Thing If Thing One Goes Away
    Life One no longer an option. What do you do instead?
  3. The Thing(s) you’d do if Money or Image were No Object
    What would you do exactly?

For myself, I found myself chopping and trading between the different blocks in these destinies and then considering them by gauges raises enough though questions you may need a fourth or fifth sheet which may even combine some of your ideas (and combine or amend timelines if they’re resource-, preparedness-, or coherence- poor).

Here’s a personal example: For some time I’ve toyed with the idea of going back and doing a PhD (or a MSc) in astrophysics or astronomy. Most universities Admissions departments are simply not set up to consider non-traditional candidates (I’m being kind here), so its been surprising how that’s forced me to amend my 5 year plan if that is, indeed, something I want to do for anything other than edification and part-time purposes (so, like… career scientist.). Sobering, but this is how you need to adjust when you actually lay and map these things out.

And keep in mind, thees plans are roadmaps based on uncertain terrain. How you get to a B where you don’t have a precise map of the route: Follow the mountains till you find a road East through the mountains to the coast. They’re directional, not prescriptive. And expect them to change over time as prototyping gives you more information on the lay of the land you discover and whether you like what your experiment tell you. So, revisit them every year or half-year. In my case, while I feel the process has been amazingly helpful (and surprising) in discarding non-starter options incompatible with life goals, I don’t have a high resolution map of the next five years. Good clarity over what to do the next 6-12 months (and 2023 especially), but farther out the plan guidance is more IFTTT (if this then that) dependent on the information I get from my prototyping. YMMV.


If I had just one piece of advice for you in 2023 on how to unambiguously improve your life, it would be: Run Experiments .

For example, I have always thought it would be a perfect future state for me to live and work remotely from a chilled, tropical island, on a beach with lots of dogs, as an indie dev. So, moving to Bali. Will see how that goes for 3 months. And then after that, if not convinced, I will try another place just in case the issue is not the mileu, but country.

Sounds scary? Not really. And I guess this is one of the most key points in running experiments: they are cheaper and safer than making big bang mistakes. In my example, taking Tim Ferriss’ Fear Setting exercise, my worst-that-can-happen downside is limited, and moving my stuff into storage and living in a lower cost country would be the same (if not cheaper) than most-expensive-city-in-the-world Singapore. Unless there is a massive tech downturn, my skills are in demand and portable, even if my current employer decides they don’t like me remoting (and I started the gig remotely from Singapore when hired.).

Still terrified at the idea of experimenting? OK, take a page from Paul Millerd’s book The Pathless Path and do a Ship. Quit. Learn. Come up with a set of three experiments you will learn something from that you can run in either 30 or 90 days.

Wanna be a content creator? Pump out a youtube video every week for 12 weeks. Take improv and do stand up. Live in a foreign country. Live on a boat. Do things just to see what they would feel like even if you don’t necessarily have the intention of doing them longer term.

Partly, this is to get into the habit of trying things where outcomes are uncertain, and getting comfy with possible failure. But it’s also a matter of avoiding the fact that for many people everything has to be perfect (or you have perfect conditions) and will last forever before trying anything new. Fear of failure is strong and culturally engrained. We need to break that.

Whatever the reason, it’s something that desperately needs to change. I’m not sure if we just need to normalize a culture of people trying new things that might inevitably (not just possibly) fail. In terms of people being able to make substantive and lasting changes to their lives at lower risk, experiments are a powerful tool that needs to be encouraged.

As an example, I try to keep a list of Experiments I’m going to run every year - usually 3 to 4 and limit those in process to just what can be managed (and not cause confounding effects). I’ve tried very hard to burn this into my life as a habit every quarter - both honestly assessing results and setting up for experiments in the future.

More to the point on life changes though, depending on what your own Odyssey Plan is and how confident you are about some of the major changes in it, it’s always a good idea to prototype changes to know if you’re going to end up wanting the changes you think you desire. So, stealing an idea from Lean Development, figure out what the smallest experiment you can make to learn about whether a projected couse of life direction is something you are actually going to enjoy. Start small and increment rather than trying to make big bang rip-the-bandaid-off changes. Add to your working base every week to constantly improve.

While media lionizes all-in entrepreneurs who max-out their credit cards when they get the Big Idea, the fact is the sidelines are littered with bodies who tried similar and failed. Survivor bias and wanting to tell a good story often outweighs the statistical facts of people who gamble recklessly. We are trying with these techniques to be smart, not just lucky.

As an example, a friend wanted to quit her quite excellent job to become a yoga instructor. My advice was to negotiate a 4 day a week workweek with her current role (which they agreed to) and start to build her practice on the one day a week. While my friend loves yoga and teaching students, it ended up she hated the business of running a yoga practice (and hiring an operator was not financially viable - the next option we looked at). Add to this the income hit of the change and we basically re-huddled and came up with alternative plans for her that might accomplish the same result without dire money consequences or doing something that made her even more unhappy than her current role.

Perhaps from the outside this seems like a failure since she ultimately did not make the life change she wanted, but it shouldn’t be. It’s actually a huge win since she inexpensively learned cost- and time-wise that something she thought she wanted and had envisioned needed tweaking or rethinking in terms of approach. Perhaps she needs to rethink the PT approach or perhaps look at a bed and breakie where she offers yoga lessons to what she wants to do in the future around yoga as a business. Something that requires a different scale and combination of commitment, outlay, and risk.

Prototyping’s value is in the learning from the experiment. Prototyping here provided invaluable information on how an imagined future state might actually be like, which allowed my friend to course correct and re-imagine what that might look like or whether it was something that made worth paying the costs for. And for some people, this might be even more valuable dodging bullets people were not thinking realistically about and avoiding mistakes. My friend’s job is now is to re-think, envision a slightly altered outcome, and see again if there is an inexpensive way to prototype that and learn if that is something she can and wants to head towards.

Same goes for almost anything you might be thinking of. Want to work for NGOs or Not-for-profits? Spend some time volunteering at a more senior capacity than a field volunteer. Want to go back into academia? Work on a few scientific papers or projects as free labour to see if you even like doing that sort of stuff day in and day out.

Be creative with your experiments, but at all times make sure the main benefit you get from the end of it is that you have learned something valuable, or even incrementally valuable in making a future decision which moves your Odyssey Plan forward.

Also, keep in mind, getting good at something is often something that makes people love a thing. Being able to exercise your skills to both help people and cause change is addictive and a main driver in why people come to learn to love things they are doing. So, working on craft particularly if you are light on those skills has benefits beyond merely making you more attractive to possible employers. This also applies to secondary or soft skills such as writing, speaking, or negotiating which can assist “harder” skills.


So, the lesson isn’t hard: Do some thinking, envision a future, come up with a plan, start working backwards to experiment and course correct as needed. Try to measure every quarter how you manage to move yourself away from things that make you less happier, and moving towards things that make you feel more fulfilled, energetic, excited, and happier.

So, since we’re a scant few months away from 2023 and people starting to think about their next year, again my two pieces of advice are to experiment and roadmap. Then evaluate your learnings from those experiences, revise actions, and adjust roadmaps. Shampoo, rinse, and repeat. The idea here is to have this process a virtuous cycle that just moves you more reliably in the direction you actually want to go.

Now, go storm the Bastille. πŸ˜ƒ

I’m always curious to hear how it’s gone for people who try these techniques and hear more about what may have worked or not worked (or worked even better) than my ideas here. What’s made a huge difference in terms of you mapping out a more joyful future you’ve obtained? Feel free to mention me as @awws on mastodon or email me at hola@wakatara.com .

Roadmap, prototype, and experiment before making major life changes. Rinse. Reapeat.

Daryl Manning


2553 Words

2022-07-14 10:19 +0800