Ways to Release Your Inner Rebel & Reap the Rewards

3 Big Mistakes that Stop People From Living their Dreams

Now, I am not saying there is anything wrong with aiming to make a lot of money. In fact, I applaud it. But it does remind me of one of the biggest mistakes people make when they want to make their dreams come true: they get lazy with the math.

Make sure you do not put off your dream for years unnecessarily. Here’s how:

A lot of people have dreams of traveling the world or simply living a modest life where they can eat out every day and not have to worry about rent or clothes.

No matter what your dream life is, make sure you actually research and find out how much this costs per year total.

Why does this matter so much?

Because people often over-estimate how much their dream life actually costs because they do not know any better. No one knows this better than travel hackers, travel bloggers, and lifestyle entrepreneurs.

Many of them have visited over a hundred countries off less than $30,000 a year because they know that the cost of living abroad is much less than in a first world country and they know exactly how much their expenses cost on a daily basis.

You do not have to calculate every penny, but take a couple minutes to calculate how your dream life would be like. It could be something like this:

  • Moderately decent one-room apartment rent in Miami, Florida (notice how it’s a specific dream location so you can research it) plus utilities: $2,860 per month
  • Grocery cost in this area: $350 per month
  • Miscellaneous costs (most people forget about these costs – gas, utensils, toilet paper, chapstick, etc.): $400 per month
  • Monthly cost for what you enjoy spending money on (different for everyone – I am going to say Crossfit membership, restaurants, and dance classes):  $200 + 280 + $180 = $660 per month
  • Total cost: $4270 per month or $51,250 per year after-taxes.

Instead of doing this, most people have some unnecessarily large, vague number of how much it costs in their head.

And they prolong ever moving towards their goals for decades. Until their youthful years are behind them and they missed out on a lot of fun they could have had.

Rather than being like them and saying something like, “Oh, it probably costs at least $150,000 to live in Miami”, you now have a specific, reachable number to aim for.

By having a specific, accurate number to aim for, you also can set goals that give you more motivation since you can see how close you are getting.

1. Are You Doing The Reverse Engineering Technique? If Not, You Are Missing Out

The second mistake average people make that stop them from achieving their dream life is not reverse engineering their dream life.

I learned that a lot of successful entrepreneurs achieve impossible goals by imagining where they would be in x number of years. And also how life looks then, before walking back to their present time to figure out what they have to do to get there. One of the first times I heard this was from an interview of the entrepreneur Peter Sage.

This reverse engineering technique works well because once again, you turn a vague goal into measurable steps you can hold yourself accountable for to get there.

Here is an example:

Let’s say my goal is to reach 100,000 subscribers on YouTube in 3 years. I can walk back to the present and realize I need 98,000 more subscribers in that time.

This means I will need to keep up with at least one video a week to have content to attract more subscribers, create content that attracts larger crowds, and try out new topics or editing styles that might work better.

But what if your goal is more vague? Let’s say you want to make $100,000 a year in 5 years but you are a lost, young man who has no good marketable skills.

Well, you cannot get super specific because you are still exploring your interests and talent, but walking back to the present can really highlight what you should not be doing and give you specific ideas on how to move forward.

You know that doing nothing will not move you towards this. You know that you need to start testing out interests and skills through internships or taking people you respect out for coffee to learn about if you would like their jobs.

It also makes it more clear that you should try to develop a skill in your free time rather than just watch TV.

2. Test out & research possibilities. Then reflect on what you did & did not like about them.

Even if you do not know exactly what your dream life will specifically look like yet, this exercise helps you identify what you like over time. Ask yourself;

“What would my life look like in 5 years for me to feel how I want to feel?”

For me, I want to feel happy, content, and fulfilled. I want to have a career and life that is fun from the moment I wake up until I go to sleep. I want the freedom to buy and do what I want (clothes, video games, travel around the world).

Knowing these feelings and broad ideas that I want program my subconscious to be on the lookout for jobs, skills, and hobbies that I actually enjoy so that I can find my passions and options.

Combine this with actual testing:

  • Reach out and talk to real people about jobs you find interesting rather than read about inaccurate job descriptions online. I wrote a post on how you can do this if you click here.
  • Take internships, part-time (or full-time) jobs, or volunteer opportunities to get a feel for what the work is actually like.

And then reflect on it. Ask yourself what did I like and not like about this job?

And you end up with a realistic picture of the what real work is like and what you are actually interested in. The mistake most people make is that they do none of this and they stay in their head in hypothetical land. This can fail because it leads to inaccurate ideas of what they enjoy or what a job is like.

By doing the fieldwork, you can:

  • Stumble across amazing, niche jobs you have never heard of that you would love.
  • Find out about tasks, ways of doing things, or skills that you thought you would not like that you love (examples include creative work, talking to people, or working alone).
  • Find out what you thought you would like but do not like (for example, manual labor).
  • Adjust your journey to move towards jobs (or businesses) that better fit a sense of fulfillment, freedom, purpose, happiness, fun, or whatever else you are striving for.

My one warning is to not get paralyzed by the all the different choices of careers out there. Studies show that more options can be worse than fewer because it prevents you from making a decision. It makes you feel worse when you have made one; even if you are better off compared to people with fewer choices.

3. It Can Take Years, Even Decades, to Find Your Passion. And That’s Okay.

As you are doing all this, do not beat yourself up if results are not rolling through quickly. I have watched every video and read every book out there on;

“following your passion”

on my own struggle. And what I found was that most people took years to ultimately get to their dream life.

The secret to how they did it was by learning about what they did and did not like through real-world experience and slowly sculpting or shifting their career to better suit that.

The best story to illustrate this came from a book called Life is What You Make It by Peter Buffett, a musician and Warren Buffett’s son.

Peter had a friend who wanted to do architecture but when he finally tried it out, it was too artistic. He then moved to a job that was part architecture and part physics, but it was too mathematical. He kept shifting jobs as he found out what he liked and did not like. Each transition took a couple years, but he eventually moved to a job he loved.


To summarize, the three mistakes average people make that prevent them from achieving their dream life are:

  1. Being too lazy to research and calculate the actual numbers for how much it will cost.
  2. Not identifying what their dream life would be like, how it would feel, and what they would do in it … and walking backwards to the present to identify measurable steps to get there.
  3. Not researching and testing out what they enjoy and do not enjoy based on reliable feedback … and using what you learned to move towards a better life.

Lifestyle design has been popularized over the last several years by lifestyle entrepreneurs like Tim Ferriss and other travel hackers. But it should not be viewed as a weird, niche interest for a small group of life hackers.

Instead, this is a practice that anyone who wants to improve their life should use. That way they’ll actually improve their life.