Stacking the Upside — have you made the most of your opportunity?

Stacking the upside is a principle that has been central to my life for the last four to five years. The ‘upside’ is what you stand to gain in a situation — stacking it means piling up what you will gain.


I’ll give you examples below from my own personal business, learning, education and career journeys. The next examples are just to ensure that the basics are clear.


If you were going to choose between two properties to buy as an investment, one which is expected to grow in value at 5% per year, and another at 10%, the one with 10% expected growth has a bigger ‘upside’.


Now imagine you’re considering two different job opportunities, but both pay the same (say $75,000 a year). In Job A, you’ll be working with the world’s most renowned thought leader in your industry, and so you suspect there will be greater opportunities down the line and someone incredible to learn from. In Job B, there’s no such prospect. It looks like Job A has the greater upside.



‘Stacking the upside’ means putting more on the ‘what I stand to gain’ end of a decision, opportunity or investment. For instance, this might be negotiating with Job A that you get dedicated time with said thought leader if you agree to work with the company.


You could also stack the upside here by documenting what you’re learning in your new job (let’s say it’s in marketing) and turning it into a newsletter or podcast. Because you get unique learning from your job, you can make even more out of that by turning it into digital assets that connect you with people online through the serendipity of social media, online communities and the internet!


  1. It protects you against opportunity cost (missing out on other good opportunities) by ensuring you get more out of any present or single opportunity (what I call a Door).
  2. It normally doesn’t take much effort, but makes everything all the more worthwhile


So let’s unpack this further and how it can be relevant to you.


First, think more broadly about currencies and what matters to you


This is an idea that Tim Ferriss’ book The 4 Hour Work Week helped endear to me.


If you’re considering a job, business opportunity, new side project or investment, there’s always many factors to consider — money is only ever one of them. Some times you shouldn’t be thinking about money at all when assessing an opportunity — it should be something that just ensues.


  1. Time is a currency — whether you get to control more or less of it, or on what terms you get to spend it.
  2. Learning is a currency — learning can be used to earn more money and release more time for your free use.
  3. Attention is a currency — I try not to give as much of it away to noise or social media, because it means I have less of it to allocate towards more important things.
  4. Opportunity flow is worth considering — Does this Door lead to a Room with more of the Doors I want? For example, I was, for a time, headed down a real estate pathway… but my interests lay beyond real estate. By over-committing to this path, I delayed the bigger, later-stage opportunities I wanted. Now that I’ve released a book, I get more book-related opportunities coming to me. You don’t get this ‘flow of opportunities’ by sitting on your arse or hiding in an office cubicle.
  5. Stress and pressure is a factor to consider too.


These are just some of the things you can be thinking about when you assess an opportunity of any form.


How can you maximise these in any given situation? — Constant Student Example.


Let’s use the example of my decision to launch The Constant Student — a new education ecosystem. It’s basically the digital version of a cool village where everyone does self-directed projects and is trying to get the most out of each part of life, without time for boring b.s. or indifference.


I wrote about it in this post, which I cringe at a little now — here I discuss how working on this online community business actually educates me way more about the world of e-commerce, online education, software, marketing, digital marketing, nocode and more.


It’s delivering me major learning and opportunity flow. That learning is worth a lot of money — I can sell it to clients in the form of a new business, I can sell it as a freelancer, or I can sell it to some sort of future employer — very likely someone within the startup ecosystem on a cool project that meets my interests.


I’m unlikely to come across and ‘afford’ (with learning and experience currency) these opportunities as the version of Joe who has not taken on the challenge of Constant Student.


I’ve both hired people who’ve had experience running a business — even failed ones, and seen other friends employ such people. These people make for the best employees, even (or especially) the ones who have failed at something! They have a broader understanding of business, and an appreciation for the role of a leader or manager.



For a lot of people starting a business has ‘risks’ — normally the money you might lose and the opportunity costs of working on another project or earning your stripes at a job in that time.


In this case, the upside is so high, and stacked taller than a set of 100 pancakes! These areas of life are all bolstered by taking on this challenge:

  • Business experience
  • New high quality relationships
  • Deepening of existing relationships
  • Networking
  • Investment opportunities, thanks to meeting more entrepreneurs
  • Learning about things related to business, marketing, education and more
  • Reputation — based on how I react and respond


And much, much more.


Return to the village analogy — this community brings together an intimate circle of like-minded people. As a result, I get even more upside:

  • A group of people who can be the support crew or early customers for launching a business or project
  • Specifically this was the case with our book, 18 & Lost? So Were We
  • Beta-testers for new products (feedback off everyday friends on business ideas is very hard to find. Everyone just tells you how lovely it is!)
  • Beta-readers for new books (super hard to find too!)
  • Gives me new ideas for future books, by bringing me into contact with more people
  • It also makes for a useful example in an epic blog post like this one! (Meta, right?)


It should be clear at this point that I can’t afford not to start the Constant Student


Failure becomes the cost of accessing all this opportunity and currency of different forms, in the same way people pay tens of thousands of dollars for limited upside.


Rapid fire examples of Upside Stacking relevant to you




I invested $10,000 in a ‘speculative’ startup which I think will change the world — hat tip Robby Wade and the team at This.


Opportunity cost: I could have put that money into cryptocurrency, shares, saved up for a property…


Except I’m interesed in great journeys, stories, startups, change-making and technology. So, regardless of the investment coming off or not, it is a degree in all these things. I’ve already paid off this investment in learning and experience.


Side note — it also gives me the ability to say I’m a tech investor, which boosts my credibility for Constant Student, without having to do any extra work.


💡 Lesson — the average mum or dad, because they don’t have as much to gain from an opportunity like this, is less able to participate in such an opportunity. Assuming it’s just some ‘thing they’ve done with their money’ and not something they’re embracing, they can’t recoup their investment in credibility, learning or experience like me.


So, if you’re investing in anything, overcome the myth of ‘passivity’. Find things you’re interested in and keen to learn about — stack the upside in this way. Your first investment in anything is your education in it. For me, putting that $10,000 in crypto would have been a huge mistake, even if that crypto made a crazy financial return, because money is just one currency that matters.


Going to university


I don’t have an absolute stance for or against university. I do however think that most people go to university with very limiting expectations, misaligned intentions and false beliefs.


If you’re going to go to university, stack the upside on the experience. Leave with a lot more than an accreditation and piece of paper (cough-cough, most people don’t even get the accreditation). Participate in the campus and the ecosystem — sports, parties, societies, random opportunities, interesting people, leadership roles, new interests… you name it.


If you’re going to be there anyway, reduce the opportunity cost of spending that time and money elsewhere by making the experience spectacular.


Taking a career or business risk


There is so much value buried in:

  • Networks
  • Quality relationships
  • Mentors
  • Discovery and opening Doors.
  • Transferrable skills
  • Unique experiences ****
  • Carving your reputation by being pro, intentional and organised in your dealings with people

I track most people I meet in one big master database called my ‘Leverage List’. Small effort, huge long-term value — when I need to find a relevant contact for something, I just hit search and… voila.


I also document most of what I learn on this blog! You could do it very easily in Medium or Substack without having to setup a website. It’s a live, dynamic CV that is always working for you.


Being exposed to a lot of new things — be it from dealing with a range of clients or doing something where you meet new people takes away a lot of opportunity cost.


If you do want to take a business or career ‘risk’, remember to embrace it in this way and ensure you’re meeting people. You should be able to land a super interesting job with someone you met along the way if you ‘fail’.


So remember my dears — always stack the upside


And keep opening Doors for others! Ta — Joe xx.

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