Setting ambitious goals: 5 “millionaire tricks” to help you smash yours

Let me introduce you to Shaan and Sam.

They’re successful entrepreneurs who’ve made millions of dollars from online businesses. Shaan sold his startup to Twitch in 2019, whilst Sam sold his newsletter to Hubspot for around $20M.

In this podcast, they talk about setting ambitious goals. Shaan’s methods are surprising. As a self-confessed “lazy person”, he doesn’t rely on willpower. He uses “tricks”.

Let’s break them down.

Trick #1: Use vision boards

I laughed so hard when I heard this back-and-forth:

Shaan: “I’m more motivated by a movie scene in my head than by text that requires my brain to do work…”

Sam: “So a vision board?”

Shaan: “Ahh yeah — I guess I just described a vision board.”

Sam: “Pinterest! Yeah, great idea!”

Vision boards go straight for feelings.

With financial goals, you get a picture of what you want rather than figuring out how much money you need. This gives you assumptions.

For example, if you’ve got a massive house on your vision board, you probably need a sh*t load of money.

I used Milanote to create a vision board about 18 months ago. I then pinned it to my desktop background. On it, there are people who inspire me, as well as rooms in my dream house. I see this vision board every time I switch on my laptop.

It reminds me of my ambitious goals.

Trick #2: Floor and ceiling goals

Shaan religiously fills out a kick-off doc when starting new businesses or initiatives. “I ask myself what are we trying to do, and what does winning look like?” 

He then ties these questions to a range of goals:

“The floor goal I set for any project is the minimum it would take for this to feel like a win […] The ceiling goal is my ‘F-Yeah!’ What would make me say ‘F-Yeah, that really worked out’?”

The floor method is how Shaan got his podcast — My First Million — off the ground. He used it as an opportunity to meet “cool people”:

“Let’s say I do one of these a week, 52 guests [a year], and half of them are cool. Then let’s say half of those cool people become friends […] I’ll make 12–15 new friends who are heavy-hitters enough that I can invite them onto the podcast […] That alone is a win!”

His ceiling goal took this further:

“What happens if people actually listen to this? Wouldn’t it be sweet if people listen to us on their commute and we build an audience of people who know, like, and trust us? That would be amazing!”

This is how I thought about my first live webinar.

Only one person showed up, and I was super disappointed – but it was still a win. The webinar gave me the opportunity to:

• Practice
• Make mistakes — I didn’t share the correct screen for the first 10 minutes!
• Write about the experience — I shared this post on LinkedIn, and it resonated with my followers

Trick #3: Set anti-goals

You might set the goal of becoming a lawyer who makes $1,000s a month.

Sounds great, right?

But if you hit this goal, you might travel the world and never see your kids grow up.

Most lawyers probably don’t say to themselves, “I don’t want to see my family,” but it could be a by-product of hitting their goal. 

To avoid the negative consequences from setting ambitious goals, Shaan sets specific “anti-goals”:

“Yeah, I want to do this podcast, but I don’t want it to feel like a bunch of work every week. I’m not trying to make this my job. I want this to be a fun hobby, right?

“All of a sudden, I’m drowning in work trying to edit this thing and upload the thumbnail and write the show notes and do all that stuff.

“That would be an anti-goal: the after-recording stuff taking five hours a week […]

“By identifying the anti-goal up front, you can make a game plan that solves it.”

I did a similar thing for my podcast. After producing the first 12 episodes, I realized it was sucking my time. So I jumped on YouTube, learned how to outsource, and hired an assistant. She lives on the other side of the world and easily saves me 10+ hours a week when I’m recording new episodes.

Trick #4: Tip of the tongue test

According to Shaan, if your goal isn’t at the tip of your tongue, it’s not clear enough.

“Also, give it a time box. Do you have ten years or one year to do this? That’s a critical element to a goal. It should be pass-fail. It should be easy to figure out if it happened or not […]

“If you don’t have a time box, you can’t ever judge it.”

Before launching his latest business, Sam used accountability to remember his goal.

It was always on his Twitter bio:

Trick #5: Don’t move unless you believe it’s going to happen

If someone says their goal is X, and you ask, “What do you think the chances are that that’s going to happen?” Most people will say, “well, it’s quite hard…”

They don’t believe they’ll hit their ambitious goals.

Shaan doesn’t take action unless he believes he can achieve a goal:

“If I really believe this person’s going to say yes and buy my product, I’ll pick up the phone immediately and call them. It’s only when I don’t believe they’ll buy my product that I’m like, ‘Well, I’ll call them after I’ve finished this PowerPoint deck […]

“It’s your belief that drives the level of action you take. Massive belief equals massive action. Massive action equals a good result, and a good result reinforces the belief […]

“Timid action brings sh*tty results […]”

I like Derek Sivers’s approach to making decisions.

If it’s not “Hell yes!”, it’s no.

Key takeaways

Want to set ambitious goals? Here’s a summary of the five tricks Shaan lays out to help you achieve them:

• Trick #1: Use vision boards — Cut the decisions. Go straight for the feelings.
• Trick #2: Floor and ceiling goals — A range of goals leads to more satisfying outcomes.
• Trick #3: Set anti-goals — Sometimes, we’re so obsessed with hitting the goals that we forget the negative stuff. Account for this.
• Trick #4: Tip of the tongue test — If your goal isn’t on the tip of your tongue, it’s not clear enough.
• Trick #5: Don’t move unless you believe it’s going to happen — Belief drives action. Set yourself up for success by only starting projects you 100% believe will happen.

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