I’m paying $1,000 for 19+ new business opportunities and 26+ new skills… and you won’t believe how.

“The only risk, is not taking any risks” – Scott McKeon


When you’re in the Room choosing between a few Doors, there is only one option that is wrong. As each Door is really the first of a Thousand Doors that lie one after another, the only wrong decision is choosing no Door.

The Door I’m opening now in my life is called The Constant Student Community. It is an online learning community to help people discover what they love doing — whether it’s a traditional career, creative side project or full-blown startup.

To be clear, this is a business I’ve co-founded and taken primary responsibility for running and operating. No one asked me to and no one encouraged me to – they didn’t need to. The idea was first hatched amongst myself and Scott McKeon, and ever since it’s excited the hell out of me to work with a team to bring it to life.

At time of writing, we are not even a month into running our first sessions with a group of 26 young people who volunteered to try the Constant Student and support the co-creation of the community going forward.

Some of the incredible ‘Pioneers’ – first cohort of the Constant Student


An important part of our community is encouraging young people to take risks, start creative projects, and open Doors. So, to get very meta, this piece is dedicated to showing them and others like them that if you structure your projects right, that there is no downside. That’s because of one simple premise:


Even if the Constant Student ‘failed’, I would still be better off than I would have been having not tried it!


Note to reader: I hope this piece isn’t trivialised by the fact that Constant Student is f*cking incredible and will almost certainly not ‘fail’.


Combined with the collateral we will earn with launching our book 18 & Lost? So Were We (which promotes the community at the end), there is a lot of momentum behind this project.


Despite that, I wanted to break this piece down into the following considerations.

  1. What I will learn, even if we ‘fail’, that I would happily pay to do a ‘course’ on.
  2. The new skills I’ll develop.
  3. The business opportunities it will generate for me. Specifically, there are things I would never have thought of, that never would have occured to me, and that I would not have the skills to operate — and these new opportunities arise even if Constant Student ‘fails’.
  4. The new people I would have met and relationships I would have deepened
  5. My ‘brand’ and the image I’d have — what if I get stamped as a ‘failure’ amongst friends and my network?


I will also talk about how as a team we’ve collectively 1) lowered the barrier-to-entry 2) reduced the downside for ourselves with the project, and 3) negated opportunity cost.

So, let’s get started!


1) What I will learn, even if we ‘fail’, that I would happily pay to do a ‘course’ on


Why push needlessly uphill with your learning?

The ‘quotation marks’ are inserted because I hate online courses — and in-person courses. They’re normally low-return-on-investment for learning, compared to the many great things we can do to learn in more fun, interesting, and economical ways.

People will spend tens of thousands of dollars on college and university degrees (that they may never use) but will be scared about spending a few hundred, or maybe thousand, on a project where they are guaranteed to learn more.


I think my exposure (which is a financial term for what I’m putting on the line and could potentially ‘lose’) would be capped at a few thousand dollars for this project. It could have been lower! Yet I don’t think of this as ‘money I could lose’ — I think of this as money I am happily investing in my own learning.

Here are some of the areas I’m gaining an education in:


  1. Paid and private online communities
  2. Ecosystem development
  3. Learning journeys
  4. Group, no-code, open-source projects
  5. Self-directed learning projects
  6. Video-based, live session facilitation
  7. Team management
  8. Business development
  9. Digital Marketing
  10. Leadership
  11. Time Management
  12. Networking
  13. Leverage and negotiation
  14. No-code technology tools, including but not limited to Notion, Typeform, Videoask, Slack, Discord, Sendinblue, and much, much more
  15. Technology stack assembly
  16. Website development
  17. Community building
  18. Digital marketing
  19. Marketing fundamentals
  20. Facilitating people
  21. Facilitating self-directed learning and self-coaching
  22. Peer-based learning
  23. Project-based learning
  24. Philosophy
  25. Storytelling.
  26. Myself. What I do and don’t like doing.


Hmmm… what does that do to my market value? Where is there a better place to put a few hundred, or thousand dollars right now? Not even cryptocurrency.

I’d like to emphasise a few things here:

  1. Nowhere else: Some of these things are being discovered and invented for the first time on this project. So, there’s nowhere in the world or online that I can go and pay to learn about them.
  2. Time-frame: I’m gaining an education in these areas over a number of months. I’m not perfecting or mastering them, but it is still deeper learning than I would get by watching online videos about them.
  3. This much at once: From the perspective of learning, the project is the only way to learn so much in such a short period of time. Think about all the different areas canvased from working on something that should actually sustain me with income.


2) Skills I’ll develop


Looking beyond what I gain exposure to, what if we talk about the actual practical skills I’ll develop through this journey?

  1. Business model development
  2. Monetisation of a new type of service
  3. Empathy — empathising with what people want in terms of support on their creative journeys and learning journeys
  4. Community development
  5. Community engagement
  6. User-activation flow — how people ‘start’ when they use a new online service or technology
  7. Leadership
  8. Team-building
  9. Marketing
  10. Planning and organisation
  11. Online event management and facilitation
  12. Sales
  13. Public-speaking, presentation skills
  14. Facilitating amazing customer experience, and customer journeys


We could go on and on with this list too! These skills definitely flow out of the areas I’m learning and dipping a toe into, but there is an important distinction to be made. Let me give you an interpretation based on the difference between knowledge and skills.


My take on knowledge vs. skills


Knowledge refers to the things we learn about, but skills are the things we learn to do. They are performance-related, and this distinction is one that normally gets lost when we think about education. University degrees are normally geared towards knowledge, whereas apprenticeships focus on skill development. I would argue that most market value (how much you are worth in the job market when getting hired) comes from skills rather than knowledge — skills take more effort to develop and acquire, and scarcity drives up value.

Seth Godin has an amusing example of this — to learn baseball, you don’t spend time sitting in class being taught baseball’s history, its core concepts, the different styles of play or anything like that. You simply go outside and begin playing catch. Your knowledge about baseball doesn’t add much, if anything, to the skills required to play baseball.


So for the purposes of this written piece, I want to make it clear that there are plenty of t

hings I can learn about but they are very different to the things I get better at doing. People don’t want to hire lawyers because they know a lot about law — they want to hire lawyers so they can stay out of prison or squash the law suit. No one wants to pay you for knowing a lot about the human body — they want to pay you to save them from cancer.

No one pays Spotify because the company knows a lot about music — they pay because they want to have cost-effective and easy-to-access music, with tailored recommendations and playlists.

The market is more likely to pay you for what you do than what you know. So, what are you learning to do at the moment, and how is that different to what you’re learning about?


3) The business opportunities it will generate for me, that I could not have done before, even if it ‘fails’


This list compiles a whole stack of things I would not have been capable of doing, or ever thought of doing before beginning work on the Constant Student Community in December of 2020. They do not require the Constant Student to ‘succeed’ either.


The Constant Student project has forced me to learn more about community, online networks, technology tools, people, and a whole lot more, which naturally generates lots of interesting new ideas and insights.

  1. Create a business of regular, introspection-focused zoom calls.
  2. Create an agency that makes engaging Typeforms for businesses to a) outsource FAQ, b) outsource customer service, c) streamline leads and website traffic, and much much more.
  3. Sell Notion consulting services (notion is a powerful online productivity and note-taking tool).
  4. Apply for a job at Notion ( I love what this company does!)
  5. Have a crack at being a Notion Influencer, by making Youtube videos and offering templates for people that make them more productive.
  6. Applying the Thousand Doors, being a Notion Influencer or consultant could lead to opportunities to work directly with companies, develop a database of innovative companies and freelancers, develop an expertise in productivity…
  7. Build Webflow websites for customers (I wouldn’t be world class, but I would do some for free for friends and then use these as a portfolio… I could also consult on adding Typeforms to these websites).
  8. Create blogs using Notion as a much more dynamic web interface
  9. Create intranets for companies and education institutions using Notion
  10. Document my failed journey at the Constant Student and release it as a Youtube mini-series, and start a movement around accepting failure.
  11. Write a book about the failure of the Constant Student, key learnings and recommendations to the education industry, bootlegged startups, community-builders and more.
  12. With the previous two ideas, I could develop a service where I consult for companies turning failures into valuable, monetisable, learning.
  13. Applying the Thousand Doors, this previous idea could position me well to do an improved version of the Constant Student, or get access to new startups to eventually invest in.
  14. I could have a crack at another community-based business, as I would have learnt a lot from failing the first time. I could do this for
    1. Some of my friend’s companies
    2. Other companies looking for community builders and managers
    3. People with podcasts and big audiences
  15. A better community running platform — I’ve noticed how the current technological landscape is lagging behind what is needed.
  16. Group coaching platforms — instead of one-on-one’s and isolated experts, leveraging a community, tribe, or group setting to challenge ideas can be more powerful, economical, and scalable.
  17. Running learning weeks at companies
  18. Connecting industry leaders CSR programs with giving back through educating young or inexperienced people with their skills.
  19. Creating a platform for companies who are committed to ‘build-in-public’ to share their stories.


I could go on… and, you’re free to take any one of these ideas and run with them. We plan to do just that at The Constant Student with people who enter the community looking for new projects to work on. But, even though I’ve listed these ideas, they are harder to execute for people who’ve never tried their hand at any sort of project before, than they are for someone who has tried and failed at projects.


4) The new people I would have met and relationships I would have deepened


Life isn’t all dollars, business and deals. The greatest opportunities we all have are sharing our journeys with one other.


I kind of want to put that line on a billboard somewhere. It’s very easy to miss, overlook, and undervalue.

Working on Constant Student so far has been an incredible opportunity to get to know a major up and coming entrepreneur and social contributor in my friend, Liam Hounsell. If we didn’t have the project to work on together, we’d have far less interaction, and we would not have had the chance to learn so much from each other over the last couple of months.


It was also the chance to bring together some great people in our networks to trial the community — our Pioneers Cohort. As a trial, this cohort was willing and forgiving, thus taking the pressure off of us, whilst simultaneously bringing one another closer into each other’s lives. This has left us wealthier already from a personal relationship as well as a contacts and networks perspective.


Through Constant Student and the book project 18 & Lost? So Were We, I’m also meeting more people in the industry I’m interested in — education. Funnily enough, it has also brought me in to help a friend’s promising startup, who wanted to support our work by enabling me to be a fly on the wall in seeing how they do things. Check out ThisApp, and a huge hat tip here to the inspiring Robby Wade.


5) My ‘brand’ and the image I’d have — what if I get stamped as a ‘failure’ amongst friends and my network?


This is always super, super intimidating when you’ve never failed on a project before — you haven’t gotten through it to see how everything will invariably be okay on the other side. Fortunately, I’ve already had that experience in the past, which I will be writing about separately as a part II following up on this piece (my first failure report).


Failure is not fatal. That’s different to being reckless and scaring people from working with, buying from or investing in you in the future. Maybe your podcast doesn’t take off, or your startup fails to gain traction or investment — and you’re worried about getting your reputation stained, or having your friends laugh at you.


Well firstly, f*ck what your friends think. Also, I used to post on social media all the time about my earlier projects, and it didn’t add that much value (if any at all). I’ve learnt my lesson — don’t necessarily blast your friends and family with what you’re doing.


Bill Campbell and Go Corporation


As for your public image, let me tell you about Bill Campbell. Bill Campbell had one of the highest profile business ‘failures’ in history — that will be far superior to anything you can muster in your lifetime. His company, Go Corporation, attempted to make an earlier version of the iPhone… but before people were really ready for the product. They burnt through $75 million of venture funding before closing shop in 1994.


Bill Campbell is one of my heroes. Once he knew things were irrecoverable at Go, he shifted his focus to finding the right buyer to take over the technology they were pioneering. Despite going down and taking a bullet to his reputation, his focus shifted to maximising what value the work they had done could offer the marketplace, and doing what he could to look after his people.


Bill Campbell went on to be chairman of Intuit (very big and famous Silicon Valley company), work at Apple and is written about in the book Trillion Dollar Coach as the hidden mentor and coach behind a golden generation of Silicon Valley innovators, including Larry Page, Sergey Brin, Eric Schmidt, and Sundar Pichai (Google), Steve Jobs (Apple), Jeff Bezos (Amazon), Jack Dorsey and Dick Costolo (Twitter), and Sheryl Sandberg (Facebook).


Would the failure of the Constant Student prevent you from hiring or working with me, based on how I’ve shown myself to think in this piece? If the implosion of Go was not fatal for Bill Campbell, then I think you’ll be just fine.


The Slingshot Principle


I’ve also made the argument before that the worst-case scenario is actually the best-case scenario, just from a perspective that may not be obvious to you. Like a slingshot, the further you get pulled back by a setback, the more energy and potential you have to fire in the other direction. Nassim Nicholas Taleb calls this being ‘antifragile’ — the opposite of being fragile like glass. He uses the word antifragile for things that get stronger when they’re stressed, like muscles in the gym, because such a word doesn’t exist in the English language.


It shines a light on the cultural problem we have with failure. Bill Campbell’s later successes and contributions might not have been realised despite his experience at Go, but perhaps, because of his experiences at Go. In the same way, if my real estate business had not been tampered with by the forces of COVID-19, I probably wouldn’t be here doing The Constant Student Community, which appears to have a much more significant role to play in making the world a better place (fingers and toes crossed).


Another story I love is Slack’s. Slack is a popular workplace communication app, and it remarkably spun out of a failed gaming company! Slack was the platform developed by the company to communicate internally — after the gaming company was in tatters, the team wondered if this communication technology would be popular in the market. Turns out, it was super, super popular. Talk about a slingshot. Talk about the Thousand Doors. If it hadn’t been for a failed gaming company, we would be without one of the most famous startup business stories of all time, and one of the most popular professional communication tools in the world right now.


“Move fast and break things” is Mark Zuckerberg’s famous quote and instruction to his team at Facebook. Failure can definitely be part of a great creative process, because of all the new Doors it opens that you could not ever have known about beforehand.


Sometimes, if not most times, failure is actually the best possible outcome.


How we’ve 1) lowered the barrier-to-entry 2) reduced the downside for ourselves with the project


A few other notes to add — as I do have a business partner in Scott McKeon (espresso displays) for this project, my ‘exposure’ is limited even further. Yet, I still get the same level of learning and Door-opening outlined above.


We’ve chosen a very lean business model to help lower the downside and risk for us in this venture. Because the whole project is facilitated online (sessions we run, interacting with people remotely), we don’t have an office, any inventory to stock and organise, and thus very simple and low costs.


Not only that, but I still operate Sydney Listings, my real estate business, which continues to provide cash flow to support me along the journey. Whilst not everyone has the luxury of a previous business to lean on, my point is that you don’t need to quit your current job to start a very high potential side hustle or creative project.


Not only that but de-risking this whole thing is the book project, 18 & Lost? So Were We — as book sales will go towards supporting the community. But, also, the community should help the book sales as well. They go hand-in-hand.


Lowering the downside is so magical because it doesn’t negate or deduct from the learning and creativity that ‘failure’ can foster. If your new business idea exposes you to losing tens of thousands of dollars, please don’t press ahead just because you read this piece! Joe said failure is the best-case scenario, after you overcome the crippling debt and broken self-esteem, so let’s go nuts.


No… gosh no! There is just one golden rule to your projects — because failure is so useful, the golden rule is protecting your downside. Make sure you’re getting as many Doors to open as possible out of it (this is part of your upside — what you stand to gain) but also limit and cap the downside — what you stand to lose. That includes time, money, and the other opportunities you pass up.


What about opportunity cost?


Joshua Hodge explains the concept of opportunity cost in our book 18 & Lost? So Were We, with relation to spending time on one thing but not realising what else you could have spent that time doing. Using the Thousand Doors analogy, if you go through Door A, you can’t go through Door B which sat next to it — if Door A is moving to London and Door B is moving to New York, I’ve got a dilemma… I can have Buckingham Palace and live EPL games, or bagels and the Empire State Building, but I can’t have both.


In other words, what if there was something better I could have been spending time on than Constant Student?


This is one of, if not the most important points for young people at the start of their careers. When Liam Hounsell left university last year, he was tossing up some of his options as to what to do next. He was already a tennis coach, personal development trainee, videographer and Youtuber. Yet, I suggested he help me run the community, arguing that it was going to be fun, meaningful, but also open far more Doors of what could come after than most other opportunities.



Note in these visuals — the community manager role is so good because it actually integrates with many of Liam’s other interests. He does not shut these Doors by engaging in this role — so, whilst it’s impossible to make a perfect decision because we never know what the other options have in store down the road, it’s possible to make some pretty good bets based on the Doors that become available.



You’ve got to understand something important here — it’s not just what you’re doing but who you’re doing it with. This project brings Liam into contact with me and my network, as well as Scott and his amazing network with what he’s done at espresso. To keep confusing you, it also helps benefit me in transferring some of Scott’s network over to being my network and vice versa.


So if deciding between New York and London, or one project or another, consider:

  • Which has more of the Doors you’re most interested in now? London has the West End in response to New York’s Broadway, so both of them have a thriving theatre culture. So, what do I value more? Being in a central part of Europe or having access to New York’s many Doors?
  • Also, most importantly… the ‘who’. Who do I know in New York, and who do I know in London?


If Liam’s heartfelt ambition in life was to be an expert tennis coach, then the role at Constant Student doesn’t make sense for him, even though Scott and I are working on it. The reality is, Liam has interests beyond tennis, and the key ones around learning and education are shared with Scott and I. That is why for all of us, this is the opportunity of a lifetime.


To consolidate it — put yourself in the place where, even if you fail, you’ll be positioned closer to the Doors you’re most interested in.


There could always be something ‘more’ or ‘extra’ one could be doing. Maybe the right thing to be doing would be doing a bit less too! We can’t be certain, but, we can reduce the risk with a scenario like the one I’ve outlined for you today.


“The only risk is not taking risks” — Scott McKeon.


The only wrong Door, is no Door.


Plot twist… I’m not going anywhere!

Cue Wolf of Wall Street reference…


Despite the many different pathways that could lead off from here, I have one final point. I actually believe so much in what we’re doing that for the foreseeable future, I would not detour off onto any of the paths I’ve outlined in the business opportunities section. I’ve had a lot of time to think and reflect on the size of the education problem in our culture, and thus my commitment to it.


Seeing what else I can be doing reaffirms to me that I’m doing exactly the right thing right now. This is the ultimate buffer against opportunity cost. Whilst I’m still open to going wherever the Thousand Doors will take me next, whilst life is rich with opportunity, that does not make me waver.


I would rather fail at this than do anything else right now. Let me repeat that, in case it doesn’t sink in.


I would rather fail at this than do anything else right now — successful or unsuccessful. When you feel that way about a project, you know you’re onto a winner. The truth of the matter is, for most people, there is better way to learn or open more exciting Doors than through a project.


The more knowable something is, the less exciting it can be. From a surprise birthday party to an unexpected discovery, the real excitement, adventure and contribution comes from the unpredictable. What is the risk that you’re blocking all that from happening, by staying in the Room you’re in now?


Remember what Scott said — “the only risk is not taking risks”.


Recommended Further Reading

  • How to run a self-directed learning project — this post unpacks the journey of how we’ve made the book 18 & Lost? So Were We — and this journey, and post, is ongoing!
  • I have bad news… the excuses are gone!
  • Coming soon — my ‘failure report’ from my real estate journey. A consolidation of what I learnt from my baptism of fire in business. Subscribe to my substack to be notified when this goes live.


Would this open a Door For Someone You Know?

Remember to share it with them, after all, the best way to Open a Thousand Doors for you is to concentrate on Opening Doors for Others.

With Joe Wehbe – The Podcast

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