Designing My Life | Part V: Alternative Life Plans Odyssey

The purpose of the fifth activity in Designing Your Life is to go on a journey to create three alternative life plans so you can evaluate how you might address the issues in your current life situation.

Each plan contains four key elements:

  1. Title
  2. Five-year Roadmap
  3. Questions this surfaces
  4. An affinity dashboard to measure:

  5. Resoures required (time, skill, money, contacts)

  6. Desireability (how much you like it)
  7. Confidence (how you feel about your ability to execute)
  8. Coherence (consistence with your Workview and Lifeview)

An Aside on The Importance of Divergent Thinking

The activity highlights the importance of not settling on your first idea, but rather diverging into the wild and even extreme.

This principle of divergent thinking plays a critical role in innovation through design thinking. Often our first ideas are not the best. They usually reflect the obvious and rarely hold the best elements of a complete solution.

I encourage any person in any field to exercise divergent thinking with deliberate practice. When solving a problem, force yourself to generate as many potential solutions before you choose one to test.

You'll spend far less time doing the wrong thing and far more time iterating and getting it right.

Three Alternative Life Plans

The three alternative life plans they encourage participants to design are:

Life One—That Thing You Do

"Your first plan is centered on what you've already got in mind—either your current life expanded forward or that hot idea you've been nursing for some time"

Life Two—That Thing You'd Do if Thing One Were Suddenly Gone

"Imagine that your life one idea is suddenly over or no longer an option. What would you do?"

Life Three—That Thing You'd Do If Money or Image Were No Object

"If you knew you could make a decent living at it and you knew no one would laugh at your or think less of you for doing it—what would you do?"

My Alternative Life Plan Odyssey

The life plans I constructed didn't follow the same pattern that the book described. The outputs of each plan were influenced by my environment and circumstance at the time.

I didn't have a printer so I drew the life design templates by hand and set out to create as many divergent life plans as I possibly could.

Four key themes emerged across the nine plans that I created:

  1. Property Investment Company for Social Good
  2. Design + Technology Education Startup
  3. Health & Wellness Startup
  4. Consulting + Homesteading (current)

Below are images of each of the plans in the four themes:

1. Property Investment Company for Social Good

Since I moved to the UK I've become increasingly drawn towards the idea of using property as a vehicle to attain financial independence while also helping vulnerable people find housing. The housing market in the UK has a long-term economic forecast of limited supply and increasing demand.

This places housing as a great investment opportunity while also putting housing at the center of so many social issues. No matter which charity you speak to in the UK, you'll likely here how the people they are trying to help suffer from a lack of quality affordable housing and ethical landlords.

PRPRTY for Social Good

The idea behind this life plan is to design a property investment portfolio that accomplishes three objectives:

  1. Generates positive cashflow
  2. Achieves long-term capital growth
  3. Provides affordable housing for some of society's most vulnerable people.

A friend of mine has a personal property portfolio that successfully meets the three objectives above. He inspired me to consider this as my first major alternative life plan.

Social PRPRTY Crowdfunding Platform

This plan is rooted in a business model similar to the concept above but with an online crowdfunding twist. The idea is to create an online crowdfunding platform where millennials who want to invest can grow capital while also providing affordable housing for some of society's most vulnerable people.

The platform would partner with a charity like Hope Into Action that would work with churches in the local community to identify investment properties and core crowdfunders.

This concept came from a discussion I had with Hope Into Action about the business model in the previous life plan. The contact at Hope Into Action described how they had seen a pattern emerging of 10-12 people in a church coming together to buy an investment property that would house vulnerable people. Their solicitors had created a simple legal structure that was repeatable and simple.

Each owner would contribute the same amount ($10,000, say) and get an equal share of equity. If an owner wanted to liquidate their investment, they would give a notice to the other owners who would then have an opportunity to purchase their shares in return for increased equity and cashflow.

The next logical step to me seemed to be to create an online platform that would support this process at scale. Thus the life plan was born around this idea.

Eco Community PRPRTY Developer

Ever since I worked on my first straw bale house build in Israel in 2011 I've dreamt of developing eco communities for people who want to live in eco homes and sustainable communities. It would be like a modern day kibbutz mixed with a eco development.

I definitely don't have the skills to enter into this business at this stage of my life, but given my history of identifying and acquiring skills to support my career path, I'm confident that I could make it work if I really set my heart on this.

2. Design + Technology Education Startup

ETHOS Design Thinking Bootcamp

I've always dreamt of starting a school of some kind. Since completing my Ruby on Rails bootcamp in 2014, I've liked the idea of running an intensive design + code school. My Hebrew immersion program in Israel ignited a desire for me to learn and teach in immersion.

I haven't yet had the opportunity, but seeing the lack of quality design and technology talent in East Anglia sparked the idea.

The downside is there isn't a huge hiring demand here either because the tech economy is quite small. Thus, my confidence about this concept is quite low.

I spent a lot of time thinking about these type of design training initiatives during my 90 days at Clearleft and I am glad they re-emerged in this process.

D.School for a Better Future

This concept was inspired by the Stanford D.School (thus the name) and more recently the Oracle Design Tech High school in Silicon Valley.

The idea is to use lean startup principles to teach students everything they need to succeed in the real world. It's all project focused. Students work in real teams to solve real problems. They have the support of mentors and are supplemented by theory from academia.

They would use modern development principles from Agile and Scrum to minimize waste and maximize learning.

I would personally apply Google Venture's SPRINT methodology to the course modules such that there was a tight structure within each of the projects with a defined 'user testing' scenario at the end which would provide student evaluations instead of grades.

Long-term this would be the most exciting career path for me, but again I don't think East Anglia is the place for this project. I can only imagine the look on British parents faces as I explained the above...

But who knows, maybe I'm wrong. If I end up having children one day I'd consider setting up a pilot program for them and seeing if it worked.

I don't have enough experience for this concept yet anyway...

3. Health & Wellness Startup

Applying Behavioral Design to MS + Other Auto-Immune Disorders

As I described in a previous post titled Venturing Into The World of Multiple Sclerosis, in November 2016 I was considering starting a social business to help people with MS live better lives. Here's a bit of the backstory:

The parallel timeline of my life has been the progression of my mother's disease Multiple Sclerosis ("MS").

My mother taught me how to walk, play soccer and ski. By the time I was twelve or thirteen she became increasingly dependent on walking aids and eventually a wheelchair.

Enduring excruciating physical pain, my mother has maintainted a persistent brilliance that radiates to all those who meet her—exuding positivity where others would form bitterness.

The question this business model and life plan would explore is:

How might we apply behavioral design principles to help people with autoimmune disorders make key lifestyle changes to help them live better lives?

Behavioral design is an emerging discipline founded by Robert Cialdini in his book called Influence — The Psychology of Persuasion. The discipline proposes a set of key principles that influence people towards change.

The world of marketing has used these principles for a long time for commercial gains, but the opportunity to use these same tools to help people live better lives is enormous.

If you're interested, feel free to read more about Behavior Design on Stanford's course site:

MedTech Platform

I met with a friend recently to discuss the possibility of creating a technology platform that provided tools for practitioners to create medical rehabilitation software and hardware for people recovering from strokes and other brain injuries.

This would also be a local opportunity here in Norwich, so I'm super excited about the prospect of this one. There are a lot of moving parts, including collaboration with a university and the need for venture capital.

The prospects for growth and human good are tremendous. So are the obstacles and resources required.

4. Consulting + Homesteading (current)

After all the divergent thinking, I stepped back and reflected upon my alternative life plans. None of them seemed immediately viable.

The more I thought through the actual execution, the more I realized that my current set up of consulting and homesteading is the most cohesive life design for me at this time.

If cohesion and simplicity are my top two priorities then this plan is the best fit for me at this time...

consulting + homesteading life plan


The alternative life plan odyssey was an incredibly fruitful and enlightening exercise for me. I realized:

  • How little I know about launching and scaling a tech startup
  • How I'd much prefer to bootstrap a business without venture capital, focusing on establishing a sustainable business model rather than raising money and scaling like crazy
  • I'm definitely not ready to consider a new business or startup right now
  • While my current life setup has its challenges, there are also some amazing benefits: solid pay, great experience, flexible lifestyle, work/life balance, meaningful contributions and impactful outcomes
  • The difficulty of consulting remotely across timezones is probably not sustainable for the long-term
  • I'd benefit from the ability to work with collaborators in-person, either by commuting each day or each week
  • While there don't seem to be significant consulting opportunities in Norwich, London and Cambridge are definitely commutable


After exploring alternative life plans, I realized that I'm actually on the right path I just need to make certain adjustments to improve my well-being and quality of life.

I'm open for new opportunities locally that would meet my needs, but for now I need to focus on making the most of my current situation rather than trying to make a drastic change by starting a social business of some kind..

Being able to collaborate in-person with colleagues is key, and given I'm due for a tour of the USA to visit clients for my contract at OpenGov, I'll likely have those needs met in the immediate future. It should be enough to hold me over for the time being at least...

What do you think?

I benefit from articulating my thoughts in words. If you're reading and have any thoughts to share, please do send them my way. I'm always happy to share ideas and hear where other people are along their journey.

You can reach me at or find me on twitter (@iamjohnellison).

Post photo by Andrew Neel on Unsplash