How to Invest In Yourself and Your Education as an Entrepreneur

A common piece of advice nowadays is to “invest in your education”

Or, “Invest in yourself.”

But many people invest money in what they think is good education (because they’re told it is), and come out worse off financially.

In this article, I share a framework for how to invest in yourself. This framework will:

  1. Lower the chance of you wasting money on education that isn’t relevant (to you and your goals). 
  2. Increase the ROI of each dollar you spend.
  3. Fast-track your path to success.

Disclaimer: this framework is designed for those wanting to be solopreneurs/entrepreneurs and forge their own path. That’s what I know, and that’s who I’m writing for.

If you’re trying to become a world-class physicist, doctor, engineer or something similar—then you should not follow my advice because I know nothing about those worlds. 


Let’s start with a few principles. 

The best education comes from actually doing things.

This is obvious. It’s cliché. But even though it’s obvious and cliché, it’s still rarely followed.

Any form of education that holds you back from action is not good education.

A course that has you spend an entire year learning marketing without launching a campaign is not a good course.

A business coach that tells you to read 25 different books before you start a business is not a good coach.

Good learning looks like a pyramid

You should first develop foundations, and then move on to specific elements.

Many people get this backwards and spend time and effort trying to learn specifics first. But there’s nothing for these specifics to rest on, so they fail.

The best way to learn is to have a reason to learn

“Investing in your education” by itself is not a good way to learn.

“Investing in your education to build a business that can replace your day job” is a good way to invest and learn.

The former leads to endless mental masturbation. Consumption without action.

The latter encourages you to take real action. And it forces you to learn the relevant things. 

The Framework

Here’s the high-level view of the framework:

  1. Decide on a project. What do you want to do?
  2. Read key books to build the mental map.
  3. Follow some sort of proven process, if there is one. (Usually this will be in the form of an online course or structured coaching program).
  4. With your newly gained knowledge: commit to a period of trial & error/self-learning until you start gaining traction. 
  5. Once you’ve gained traction, invest in structured coaching for both accountability and direction.
  6. Finally, invest in one-on-one calls with specific experts to close gaps, capture opportunities, and fix bottlenecks.

Let’s dive into these in more detail. 

Deciding on a project

As a new entrepreneur

If you don’t have a project in mind, then you need to come up with one. Remember, the best way to learn is to have a reason to learn.

My personal take on this is that people spend too much time trying to figure out what to do (including myself). You’re better off choosing a project and adjusting course along the way than spending months (or years) trying to find the optimal business to start.

But if you’re completely new to business, here are a few guidelines for deciding on a project:

  • It shouldn’t require a ton of upfront investment
  • It shouldn’t require a multi-year learning curve just to offer the service or product
  • If you’ve never started a business before, you should be able to make your first dollar within 90 days
  • It shouldn’t feature a ton of moving parts
  • It should already be a proven model in a proven market (you’re not the first person to do it)

As an existing entrepreneur

If you’ve had success in the past but want to continue your education and build a new business, then the approach is a little different.

Most likely, you already have a bunch of ideas anyway. But if not, here are some guidelines:

  • You should be able to leverage your existing skillset in some way
  • It should be a challenging enough project that forces you to learn new skills/frameworks/information. It’s not just a “repeat” of what you’ve already done.
  • If it’s something that seems awfully simple to you but complex to others, it’s probably a good thing to pursue.

Building the foundational mental map

Most people jump right into a course or coaching program that teaches a very specific methodology.

This is a much better approach than not doing anything, but I think there’s a step before that that’s worth taking.

And that is to build the foundational mental map of “business.”

I’m not saying you need to get an MBA. But you should internalize some key mental models so that everything else you consume makes more sense.

The best way to do this is to read some “foundational” books.

I have a “basic business stack” which includes:

I’m confident that if new entrepreneurs read through these 6 books before starting their business, they would have a much higher rate of success.

“But Sam, what about [insert book?]”

Of course, other books could fit in this stack. There are many great books out there that can help teach this foundational mental map. But I don’t think you should be reading more than 5-7 books to build your map.

Sure, you could read a book like Traction, or Scaling Up, and you might learn some interesting stuff. But those book are for CEOs and entrepreneurs who have teams, are already making sales, and so forth. Better off learning things you can apply right away (in the planning/validation phase).

If you’re not sure where to start with building this map, then feel free to read the basic business stack I’ve listed above.

I do encourage you to treat this reading phase as a project in itself. It should not take you months to read these. You should treat your reading the same way you would any other project—put in hours every day in an intense, focused fashion until you’re done.

Aim for 2-3 weeks. If you’re short on time, a month. No more.

Finding & following a proven model

Once you’ve built this foundational mental map, it’s time to follow some sort of structured learning that leads you toward a specific outcome.

Usually, this will be in the form of an online course or group coaching program, depending on what you want to do.

I’m a firm believer that trying to reinvent the wheel and trying to come up with everything on your own is a bad idea.

Online courses can be extremely valuable for people who are willing to apply themselves.

I say can, because a lot of them are poor quality.


Let’s say you want to build an agency.

Something like Affluent Academy would be a good move.

e-commerce? Lots of options there.

Ecommerce Equation is a good example.

You get the idea.

Once you’ve found a solid option for what you want to do, it’s time to learn and do the work.

The temptation at this stage is to try and innovate and be creative. I think that’s a bad idea. You should follow the process to the T. Trust the expert. Do what they say you should do.

The people who deviate, or think they’re smarter (despite not having made any sales ever) are the ones who often fail.

How do I know if a course is actually good?

Like I mentioned, a lot of courses suck. The last thing you want is to be misled by bad information.

There are a few things you can do to look into the quality of a course.

  1. Check to see if they have a reasonable refund policy. This lowers the risk for you.
  2. Ask around (Twitter/Reddit/Facebook) in the right communities
  3. Get in contact with previous students and ask their honest opinion

Commit to a period of trial & error/self-learning

This is an important step in your self-education and it’s a step that few people ever get to.

Most people fall into the trap of perpetual “learning.”

They read a few books, take a course. If they’re lucky, they might make their first dollar.

But usually they end up taking another course. Or reading another book. Or changing their business model yet again.

In short, they are afraid to actually do the work and put skin in the game. They are afraid of not having their hand held throughout the process. Most importantly, they are afraid of failure.

You don’t want to be this person.

Instead, after you’ve found a proven model and you’re following it, you should fully commit to it.

During this process, there will be a temptation keep “learning.”

But you should avoid this. You need to follow the model and figure it out.

For example, let’s say you want to build an agency and the course you’re taking says that the first step is to design and validate an offer.

The way you validate this offer is by jumping on the phone with potential clients.

And the way you find those potential clients is through cold email.

A large percentage of people when confronted with this information will grate against it. They’ll think, “Well, there’s gotta be a better way than jumping on the phone. What about just communicating through social media?”

And when they hear “cold email.” They’ll think, “Cold email? That’s an old approach. I’m gonna do short form video on TikTok.”

And they will most likely fail.

A small percentage of people will say “screw it” and follow the model presented to them. They might be scared to certain things (like jump on the phone), but they’ll do it anyway.

When you’re one of the few who actually do follow the model, you need to realize that it’s going to take some trial and error. Your learning will continue.

You’ll cold email a bunch of prospective clients and get a low response rate. You might change a line or two in your cold email template and find that the response rate increases. Boom. You’ve learned something.

On the phone with prospective clients, you notice the calls start well but the energy dies down toward the end. You look at the questions you’re asking and realize that some simply aren’t necessary, so you remove them and the calls shorten and prospects are more engaged.

You get the idea.

This kind of learning can only happen through trial and error. It requires full commitment to the process.

The reason why this step is so crucial is that it’s the step that makes the difference between those who end up actually succeeding and those who forever bounce around in uncomfortable comfort of “perpetual learning.”

Structured coaching & accountability

Once you’ve gone through a fair bit of the trial and error phase, your business is humming along, and you’re starting to “get it.”

It’s time to level up.

One way to do this is with some sort of structured coaching and/or accountability.

There are two main options here:

1. Join a coaching program that also includes a curriculum

2. Hire a coach that meets with you regularly

The first option can be useful depending on the business you’re in, but if you’ve already gone through a course and the trial and error phase, you might not need a “curriculum” necessarily. You just need pointers and feedback specific to your situation (which a course can’t provide).

The second option is well worth pursuing. The best situation is to be meeting regularly with someone who understands you, your characteristics, and your business.

They don’t necessarily need to have built a business in the field you’re trying to build in.

In fact, I worked with a coach for an entire year who didn’t know much about my field of business at all. But he helped me operate better, and that’s what mattered at the time.

The challenging piece here is finding the right coach. Because as you know, the coaching industry is saturated with people who probably shouldn’t call themselves coaches.

The way I found my coach was through YouTube. I loved his content and the way he thought about things, so I enquired about coaching and the rest is history. That’s one approach—if you get value out of someone’s content, then you’ll probably like them as a coach.

Another approach is to pay for a one-off coaching call with them instead of committing thousands of dollars for multiple weeks. If they don’t allow this, or some sort of intake/strategy call (that gives you an idea of their approach), then stay away.

And finally, ask your network. Or the wider network on social media. Getting recommendations from friends and peers usually works out fine.

Specific Coaching

The tip of the pyramid is investing in one-on-one calls with specific experts.

Tools like,, and even just direct contact with experts asking if you can pay for their time come into play here.

At this stage, your business is likely humming along well. You’re probably a few years in (unless you’re operating at lightspeed), and you’ve learned a ton.

But there are bottlenecks and opportunities in your business. And you know it. But you’re just not sure how to solve them/capture them or think about them.

The books you’re reading are somewhat helpful, but not specific to your situation.

You’re kinda beyond the point of a course that teaches a structured method. There’s no blueprint for what you’re dealing with.


Someone out there has done what you’re trying to do. Or at the very least, they can help you think about it.


This is the ultimate obvious-but-no-so-obvious hack that many entrepreneurs simply don’t take advantage of.

Not sure how to structure compensation for a star employee who wants more financial upside in the business? Worried about making a mistake?

Talk to someone who’s done it!

Working on a go-to-market strategy for a new, unique product line that the market hasn’t seen before and you want to ensure you maximize the launch?

Talk to someone who’s done it!

Will it cost you? Yes.

Will it produce ROI? Almost definitely yes.

I shudder to think about the tens of thousands of dollars I’ve spent on masterminds that could have instead been invested in one-to-one calls like I’m describing.


That’s it. A simple framework for investing in your education as a new or existing entrepreneur.

In recap:

The three principles of good self-education:

  1. The best learning comes by doing
  2. Good learning looks like a pyramid (fundamentals first)
  3. The best way to learn is to have a reason to learn

And the framework:

  1. Decide on a project. What do you want to do?
  2. Read key books to build the mental map (highly theoretical, but important)
  3. If there’s a program/online course that teaches a proven process, and it’s reputable, then take it—making sure that you actually put in the work (less theoretical, more action-based). Bonus points if this course is cohort-based.
  4. Commit to a period of trial & error/self-learning until you start gaining traction. Why? Because there’s a huge temptation at this point to jump to another program, course or book instead of taking what you know and figuring it out. You also need to learn how to think for yourself.
  5. Once you’ve gained traction, invest in structured coaching for both accountability and direction.
  6. Invest in one-on-one calls with specific experts to close gaps, capture opportunities, and fix bottlenecks.

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