TLDR: How to find the perfect idea for business/career that is an intersection between all of your skills, your interests, and the ideal market. Avoid wasting years working on the wrong thing.

When it comes to business, entrepreneurship and the making of money. We often find ourselves going down a path towards ‘success’ that the best long-term investment of our energies.

Smart people tend to figure stuff out. And most even thrive in environments where there are challenges put in front of them. That’s to say that a very talented entrepreneurs can spend years making the wrong idea work, just because.

The last thing you want to be reading is how the thing you’ve invested the last 4 years of your life into isn’t the right thing (even if it might conventionally make money and work).

So i’m not here to talk about the viability of business models and ideas, there are tons of great ones out there that are profitable that you personally shouldn’t pursue.

And why? Isn’t a good idea just a good idea that can be done?

I bet this is the point where you think I’m going to talk about finding your passion, and doing some kind of work that you skip to every morning after you glided out of bed without the slightest bit of anxiety or existential dread.

I think searching for that bliss is a scam myself, but that’s an article for another time.

No, I’m talking about the most competitive business you could be working on. One that sits at the intersection of the stuff you are good at and the stuff you actually like doing.

I was re-listening to an old Naval podcast about the getting of money and building wealth. One of the things he keys on, is finding something that you can do better than anyone else.

We can’t all be the world’s best copywriter, or programmer, or writer. So what’s an average joe supposed to do?

Naval contends that the thing you can be no-contest the best at, is being your authentic self. No one can be a better version of Joe Rogan, or Tim Ferris, or Mark Manson. Which is why money comes to them by the truckload.

So your niche chosen for making money should come from within. Your authentic self. Only then can you be certain that if you execute you will win. Because competing in a niche that doesn’t align… means you are probably competing with someone who absolutely loves that shit. Which one will work harder, longer, smarter?

The true advantage you can give yourself (paraphrashing Naval again here) is loving the work that simultaneously is building your competitive business edge. If the juice of your business feels like play to you, you will beat all the guys and gals for whom it does not.

The movie critic that loves to watch and talk about film more than anything is going to beat the guy that just saw the search traffic trends looked solid in things related to cinema. Am I making sense here?

Let’s recap what we have so far:

  • We need to find things we are good at
  • We need to find the activities within those things that feel like playing to us
  • We need to intersect the above with Industries and Markets that are big enough to support our aspirations.

Fortunately on the last point, i think you can make a life changing sum of money in just about any niche or topic if you’re crazy enough about it. But the first two require you to really sit down and ponder just who you are, what you spend you time on, and what are you actually good at.

I write this article sitting atop my own existential entrepreneur crisis of sorts. I wonder if I spent the last few years working on hard problems in a great market just because they were objectively so.

And I worry that I’m losing out (at the low points and struggles of cash flow/success) to the competitors that love the space, whereas I am cool and indifferent.

What a better time than to perform this exercise for myself, and provide some structure for you dear reader. Should you find yourself in need of a similar self-inventory.

What Are Your Interests – Self Evaluation

What are my interests? What kind of stuff do I enjoy spending my time doing or thinking about doing?

  • Unconventional Adventures
    • Long Term, Sustainable Travel
    • Riding motorcycles through new and increasingly questionable places
    • Sailing anywhere.
  • Building (Hacking) Ideas together with code.
  • Building actual things to sell (vs. info products/consulting)
  • Writing in Non-Fiction (Copy/Articles/Books) and Fiction forms (Stories, Movies)
  • Dating, Relationships, and the pursuit of bettering both.

What Are Your Skills?

So that’s what I like. Now for the hard part. What am I actually good at? What skills (if any) have the last 10 years in business yielded me with that are worth building on?

This part I think ideally you could survey those closest to you anonymously (particularly your Mother, and best friends) because we often aren’t aware of our most admired traits.

Often times it feels like we aren’t aware of our most admired skills, because those are the things we take for granted (that come naturally). So it’s a useful exercise to ask people.

I’ll try and do some introspection into my own here.

Building rapport and friendships

Being charismatic and likable has always been a sneaky skill set of mine. It’s helped forged friendships on the road, and close sales despite not really having the ‘chops’ of a killer salesman.

Cutting to the Core

Whether it’s dissecting a theoretical argument, or building the smallest hunk of junk application that actually does something useful…. I’ve always thrived at simplification and iteration.

Rapid learning and the first half of the learning curve —

this might be a curse just as much as skillset.. .but i always love diving in and learning the first big chunk of a new technology, or skill. Going from zero to ‘better than average’ is insanely engaging for me and lights me up. Past that… I usually lose interest. Leading to a ‘jack of all trades, master of none’ type distribution of my personal skillsets.

This is also a super useful skill when it comes from going to 0 to 1 in a startup/mvp type situation… but not ideal for the marathon that is building an iterating on a product for the long haul.

Writing just about anything —

Little creative video scripts, love letters over email, or just big analytical articles like this one bring me a lot of satisfaction, and I’d say my ability to express points (and persuade) through the written word has now climbed above average and is approaching excellent.

Bridging the Gap Between Nerdom and the real world

I am certainly an above average software engineer… but not a top 5% one that a company could be built around. In my career, I attribute most of my success to being solid, professional, but mostly just exceptional in my ability to ‘sell’ my services and build trust with non-technical partners and clients. I thrive as the go-between between the hardcore engineers (that I like to find and hire) and the business/product folk that barely know how to use WordPress.

I think if i had to go out and get the highest paying ‘real job’ possible, it would probably be something like a solutions engineer who spends their days talking to customers about real needs and then selling them technical solutions to fit. Or maybe working in venture capital, and getting up to speed very quickly on a new company/technology to sniff out the real deals from the bullshit artists.


My mind cranks into gear when it’s time to actually start building something real. I’m always the driving force between ‘oh yeah what a great idea’ and ‘OK, but how would it actually work if we built it?’.

Evaluating the Opportunity

Not all businesses are created equal when it comes to staff, skills and product. But let’s not forget about the importance of industry, market conditions, and timing of the opportunity. A rising tide lifts all boats, as it were. So ideally, we are selecting an idea that not only suits our skills and interests, but exists in a growing industry we can compete in. Some industries would cost billions to ‘break into’ in any meaningful way (good luck on your telecom/fiber startup buddy), while others are wideee open and can be cracked with a laptop and a few amazon giftcards. So let’s add a few additional evaluation categories to our calculation here.

Value of the Industry

How juicy is the industry you’re planning on entering? Are we talking Artificial Intellgence based Virtual Reality… or Beanie Babies that look like presidents? Take notice of the size of the market and how much people are already spending on widgets/services there.

Ease of Competition

How much time and capital will it take for you to be the best of the best? Like we mentioned before, to be the best cell network provider would take billions… but to be the best violin player that simultaneously manipulates puppets with her feet would be far quicker.

Does it Fit Your Lifestyle

This is an often forgotten one in the world (less so our world obviously). Does your career offer yo uthe time and freedom location that suit your ideal lifestyle? A lot of people say they love to travel, and then become a full-time ER Nurse… no alignment there.

Whatever your ideal lifestyle is (i’m guessing it’s similar to mine in the sense of wanting complete location (work where i want) and time (when i want) freedom.

I could make a pile of cash working in high frequency electronic trading in Chicago. But, I’d be chained to the desk for years and years and thus not able to live the life I truly want. This category deserves very careful deliberation.

Working with ‘Your People’

Listening to a Derek sivers podcast, he also hit on an interesting point of “what kind people do you like and admire the most?”. His point is that in the ideal world, you business serves and puts you around the tpe of people you most enjoy hanging out with and serving. This makes total sense, if you love writers and all your heroes are writers… ideally your vocation puts you around writers on a daily basis.

If you love the energy of tech people and nerds, then a nerdy solution makes the most sense. I’m not 100% sold on this either… and consider it more of a luxury than an absolute necessity. When you’re building a business with the aim of giving yourself as much personal freedom (time and location) as possible… then I’d imagine it’s pretty easy to put yourself around your favorite type of person regardless of whether or not it’s your business.

Calculating Your Edge – The Skills/Idea Matrix

So now that we’ve gotten a good smattering of advantages and skills down on paper, i guess it would make the most sense to take a few potential career options and throw them in the ‘matrix of some kind’

Let’s try and rank each one 1-10 for possible fits and alignment. Add a small multiplier factor for ‘importance’ of the category, and then just add up the scores at the end of the day.

Below is a snapshot of the excel sheet i built to calculate (comment if yo uwant a copy of it), let’s walk through a quick example to see how it’s working.

  • I wouldn’t really get to leverage my writing skills at all (so it’s a 1)
  • But I WOULD use my communication skills from Technologiest to Normal/Corporate person to the max (so it’s a 10)

Take the idea of ‘Solutions Architect for a Big Tech Company’.

In theory, this little matrix could be used to calculate and quickly evaluate any new career path or idea.

So i’m not sure we can possibly exhaust every avenue of earning a living or business idea i’ve got rolling around in my head here… but i think the framework does prove to be useful when kicking around a new potential career trajectory or idea. Might also be prudent to add a ‘weighting’ calculation to make certain categories more valuable than others (for example, a biz that fits my lifestyle goals is far more important than a biz that is in an easy niche)

What Does Your Matrix Look Like?

I’m curious to see what other people’s spreadsheet would look like (if they find this kind of exercise useful). Hopefully at the very least this post has given you a framework for evaluating the infinite possibilities in your own life and career.