From idealist to pragmatist: The founder’s biggest hurdle

Most people start companies because they are idealistic and want to turn their ideal business into reality.

Unfortunately, in order to make their ideal business come true, they have to gain mastery over their ideals and learn to be pragmatic.

The master of your ideals

The first time founder is full of ideals.

“I want to be a great employer and create a fun work environment”

“I want to make a billion dollars while saving the planet”

“I want to work the 4-hour work week”

“I want to become a secret millionaire”

The problem is that many of these ideals actually conflict with each other. When combined, they lock you in and prevent you from moving forward. They become your master.

For example, “I want to work the 4-hour work week” and “I want to make a billion dollars” are two ideals that make it almost impossible for you to succeed.

Those two might be obvious, but there are plenty of other non-obvious ideals that conflict. Some times these can be a combination of business ideals and personal ideals.

For example, “I am someone who always sees things through” and “I want to build a billion dollar SEO company”. It’s impossible for me to say how things will play out with AI and SEO, but if you’re someone whose personal principle is basically “I’m very stubborn”, it’ll be hard for you to pivot if things don’t go your way with AI. You’ll get stuck and have a very hard time figuring out why you feel so stuck.

The true master of their ideals is someone who has reflected upon their ideals, kept the ones that truly matter to them, and let go of the ones that are holding them back.

This is also the path to pragmatism.

Why is this hard?

An ideal is a tightly held optimistic belief about the world and/or yourself.

Letting go of an ideal is akin to letting go of a world view.

It’s like convincing yourself you’re not fat, poor, or ugly. Regardless of whether you are or you aren’t, letting go of the belief is really really hard.

Here’s the other thing, ideals become more or less useful as you progress. Ideals that served you well in the beginning, that were the catalyst for your growth, might become dead weights that are actively holding you back.

Let’s take OpenAI as an example.

At the start, the ideal of OpenAI being super open about their AI model and being not-for-profit was probably very useful. It attracted people to its mission and allowed them to hire high quality employees in its early days.

However, as things progressed, it became clear they needed billions of dollars to keep going, and the not-for-profit, open ideals started conflicting with their commercial reality.

So, what did they do? They chose to discard those ideals and partner with Microsoft instead.

To be clear, I’m not interested in discussing the merits of this decision.

My intention here is merely to give you an example of a prominent company, which started with a set of ideals, then changed them along the way. All companies and leaders have to do this if they want to progress and grow.

As the saying goes, “what got you here, won’t get you there.”

A good founder is able to wrestle with and let go of ideals that no longer serve her. Most people are not capable of this. That’s why it requires mastery.

The conveyor belt of trojan horses.

Here’s the thing though – you will never encounter a problem and think to yourself, “ah! Here is an opportunity to master my ideals!”

Instead, the problem of mastering your ideals is hidden inside trojan horses that take the shape of other problems.

What does a trojan horse look like?

As a founder, you encounter problems every day, some are easy to solve. And others are difficult, but solvable with time and effort.

But occasionally, you encounter problems that feel completely different. On the surface, they seem easy to solve. And when you talk about them to your founder friends, it seems like the solution is pretty obvious.

But, for some reason, you just can’t bring yourself to do it. For some reason, this problem feels deeper to you. And to solve it, it feels like you need to let go of something you hold close to your heart.

The actual problem doesn’t matter, it’s the feeling that’s key.

That stuck-in-the-mud, unwilling to relent, going-over-it-and-over-it-and-over-it, heart-wrenching, soul-tugging, I-know-what-I-need-to-do-but-I-just-can’t-bring-myself-to-do-it kind of problem.

Congratulations! You have encountered a trojan horse problem!

Here are some common trojan horse problems:

  • “Should I market on social media?”
  • “Should I raise my prices?”
  • “Should I hire?”
  • “Should I do Black Friday sales?”
  • “Should I pivot?”
  • “Should I fire a customer?”
  • And on, and on, and on…

As you can see, none of these problems are particularly difficult or novel. Millions of founders have solved them before.

But every founder you know has had an existential crises trying to grapple with an inane problem like this. Because that particular problem was a trojan horse for them. Different founders have different trojan horses depending on what ideals they have.

The never-ending conveyor belt

The good news is that the trojan horses will keep coming at you until you master your ideals. So you’ll get unlimited attempts until you do.

The bad news is that the trojan horses will keep coming at you until you master your ideals. So your business might literally die trying.

Fake fixes and self-sabotage

Let’s revisit the common trojan horses I mentioned above.

Let’s look at the first one:

  • “Should I market on social media?

Maybe you don’t want to do it because you might have the ideal that social media is lame and you don’t want to become the next Gary Vee sellout.

The reality is, you can simply choose not to do it. Lots of companies are huge without ever marketing on social media.

The other reality is, lots of founders figure out social media and make it work for them.

The pragmatic view is: whether or not you market on social media has more to do with the type of product you have and who your audience is.

The pragmatic founder that’s mastered her ideals would approach it like this: “ok, my audience is on Twitter, so I need to be there. And if I don’t want to be on Twitter, I might have to market to a different audience or change my product.”

But the idealistic founder who’s a slave to her ideals might spend weeks agonising over this decision. She knows that building a personal brand on Twitter might really give her business the exposure it needs. But at the same time, she is fundamentally opposed to Elon’s hell site.

After much deliberation, she decides she’ll do SEO and content marketing instead.

On the surface, it looks like she’s made a decision and hence fixed the trojan horse. However, she hasn’t actually mastered her ideals and approached the problem in a pragmatic way. So this is actually a fake fix. And the conveyor belt of trojan horses continues.

Let’s do another one…

  • “Should I hire?”

Maybe you don’t want to hire because you’ve always idealised staying small and being a Company of One. You got into this to create great products, not be a manager.

The reality is, it’s totally okay to be a company of one. There are lots of one-person companies out there.

The other reality is, lots of companies grow.

The pragmatic view: Whether you hire depends on your goals, the type of product you sell, the type of business you’re running, and the skills you have, and your willingness, ability and time to learn new skills.

The trade-offs are painful to accept, but they’re actually pretty straightforward. The reason they’re hard to accept is because you’re likely holding two conflicting ideals (e.g. “I want to run a billion dollar business” and “I want to have zero employees”) and are unwilling to give either up.

The idealistic founder might spend months wrestling with this problem. Business is booming so she’s bogged down by work and it’s easy to keep pushing off the decision. She tells herself that she has no time to post jobs, interview, hire, and train an employee right now anyway. There’s just no time!

Instead, she fakes a fix by committing to ploughing ahead and saying something like “it’s difficult, but I want to become the world’s first billion dollar zero employee company”. In reality, she’s just self-sabotaging and unnecessarily narrowing her chances of success by being a slave to her ideals. And the conveyor belt of trojan horses continues.

How to actually fix

The only way is through.

It’s unlikely you’ll master your ideals and become more pragmatic on your first trojan horse encounter.

But over time, you’ll slowly learn to unclench your fist around your tightly held harmful ideals.

Talking to other, more experienced founders helps. You’ll find they’re extremely pragmatic. On a superficial level, you might approach them with your trojan horse problem and it’s helpful to hear their approach to solving it. On a deeper level, seeing someone who has mastered their ideals, shows you that it can be done and gives you a model for what mastery looks like.

Ultimately, you just have to be honest with yourself. Notice when a problem is causing more pain and making you drag your feet more than it should. In all likelihood, it’s a trojan horse, and you’re about to get tested!

Good luck!