How to be happy and the reality of “more”

If you hang out in entrepreneurship circles enough, or maybe more pointedly in “wantrepreneur” circles where people talk about wanting to start a business, you’ll see a few statements recurring:

  • “I just want to have a six figure business”
  • “I want to be a millionaire”
  • “I’m aiming for a seven figure business”

There are these levels of accomplishment that many look at as a goal, as something to strive towards.

And while I have accomplished the first one (but not the second two yet), I can tell you that what most people are aiming towards with these arbitrary goals is not the thing itself, but rather what they think that thing will get them.

  • People don’t want a six figure ($100k/yr in revenue) business necessarily. They want to make more money than they are currently making.
  • People don’t want to be a millionaire necessarily. That is coded speak for not having to worry about money as much.
  • People don’t want a seven figure ($1M+/yr in revenue) business necessarily. They want the prestige that they think comes with that.

We always need to dig below the surface on “goals” and “dreams” like these to look at not only what is really being pursued when statements like these are made, and at the same time should look at those who have achieved these things to ask the following questions:

  • How did they actually achieve it?
  • Did arriving there get them what they thought they would get?
  • Were they happy then?

Growth depends on systems, not goals

One of the biggest frauds of our day is hucksters online selling “the one weird trick that 10x’d my income”. According to digital marketing tool company Conductor, blog posts that do not leave uncertainty (eg they use numbers in the headline to set expectations or hook you) perform better than those that are “normal” or “how to” content.

Here’s the truth: you probably cannot “hack” your way to a profitable business that supports you and others by writing a ton of “11 weird tricks to do X” types of content. You’ll be competing against the likes of companies like Upworthy that have a ton more talent and resources at their disposal than you do.

When you start to dig into why a business has succeeded, there are usually a number of factors you will find:

  1. The founder is really experienced at an acquisition channel like SEO or Facebook Ads;
  2. They are the first mover in a market and the founder/founding team has experience in that market;
  3. They failed before and pivoted a bunch of times to get to where they are now;
  4. They’ve been at it for years.

Interestingly, they often forget to talk about any of this. If you’re looking at someone you respect, take the time to dig into them personally and see when they started. I bet they’ve been practicing their craft for a long time.

And beyond all of this, there is usually some stroke of luck that helped. For example, when publicly traded company Zillow (disclosure: I used to work there) launched they came out with their Zestimate. About two years later the 2008 US financial crisis hit. Their Zestimate became used even more often because homeowners were obsessed with tracking their home value. Other companies have benefitted from similar things (though maybe not on as big of a scale) such as competitors blowing up or finding the right mentor.

At the end of the day, when you study a successful business or entrepreneur you’ll find that they have systems set up that allow them to succeed. Their systems will be different from yours, but you’ll also hear some platitudes that hold true:

  • To survive as an entrepreneur you have to be mentally strong, but that comes from taking your knocks;
  • Being mindful of how you are gifted or not gifted as a person is the best thing you can do for your business;
  • You should probably go to therapy at least once, and probably ongoing;
  • Having great people around you is the best indicator of future success.

Entrepreneurs who start businesses that succeed have set up systems within their lives and their businesses to allow them to scale.

As Tim Ferriss says in his book The Four Hour Work Week, he’d check in and see that more money was being deposited in the business accounts than they were spending and “all was right in the world of automation”.

Automation is one type of system. There are many more.

A milestone is a psychological trick

Let’s do some math for a minute.

$1,000,000 is how many dollars greater than $999,999?

The answer is obviously 1 dollar.

But if you have the former then you’re a “millionaire”, and if you have the latter then you’re what?

I have no idea.

It’s literally one dollar different. And you can go from being a millionaire at one moment and then not being a millionaire after you give that homeless person in the subway a dollar.

A milestone like “a six figure business” or being “a millionaire” probably will not get you what you are wanting, which could be anything from prestige to financial security and personal freedom.

Don’t get me wrong – having more money does make all of these things easier.

But they’re level set. If you are making $100,000+ dollars a year and don’t feel successful yet, then your issue is not one of money but rather expectations.

There is absolutely nothing inherently wrong with wanting to make or wanting to be successful at whatever you choose to do. But, don’t get caught in the idea that “being a millionaire” or some similar nonsense is what you are really after.

More begets wanting more

There are numerous threads on sites like Quora where the question “How much money is enough?” is asked. Sometimes (often?) the questions is purposefully asked to wealthy people.

The numbers change (a millionaire will say “another million” whereas someone with less will usually say something less), but the answer can always be boiled down to “more”.

Humans are curious creatures. We have this incredible ability to overlook the pain that got us to somewhere and only remember the good parts of it. Why else would people run marathons?

Story time.

My wife and some friends and I did a 100+ mile bike ride in Sonoma County in 2015 (a week after I got laid off, which I highly recommend if you get laid off then you do something really hard like this because it’s great therapy) that also happened to have 9,000+ feet of elevation climbing. I’ve not run a marathon, so this is by far the hardest physical thing I’ve done. But when I look back at it three years on, I seriously consider signing up for another one because “it was so fun!”

Reality check: it was not fun. It was miserable

But my brain tricks me into thinking it was fun so that I might do it again. The same thing happens with women who give birth, people who start businesses, and more.

We also forget the bad, and once we’ve been through it we’ve level set ourselves to a new level.

If you own a home, then you probably remember not owning a home and how big of a goal it seemed to be. Now that you’ve done it, you might be thinking about how you buy a second home!

If you are a millionaire (so I hear), then you’re wanting more money than just that million even though before you were a millionaire you just wanted to reach that million.

As we grow then we tend to surround ourselves with those who are at our level and slightly ahead of us. There will always be someone ahead of us!

Story time

When I lived in New York City, I was single for the first 18 months I was there (I eventually met my wife there). I was online dating (OK Cupid was my drug of choice), and even though I received a good number of replies from women I messaged I would also get ghosted by women. This happened to a lot of men (so much in fact that there are dating sites where women have to be the ones to message first!).

I asked some women I know platonically why this was, and I heard multiple times “Well, sometimes I don’t reply to anyone who messages me because I always think there is someone better out there in New York that that guy.”


There is always someone out there who is better looking, wealthier, stronger, or smarter than you.

The more you have, the more you want.

I’m not against more. I’m not against building extreme wealth (though I am against extremely wealthy people being selfish). I want to be (and consider myself to be) successful.

But we always need to remember that “more” is something that inflicts all of us, and real success/wealth is being happy where we are even as we pursue more.

That is the only real way to be happy.

2 thoughts on “How to be happy and the reality of “more”

  1. “The Person Who Says It Cannot Be Done Should Not Interrupt The Person Who Is Doing It.”

    – Chinese Proverb

    How often do we hear that we might not succeed with what we set out to do?

    Do we get support from our friends and family?

    Do we believe in ourselves?

    I had quite a lot of negativity directed my way and weird looks when I started to launch my business beginning of this year.

    People said to me: Are you sure that you can do this? What if it doesn’t work out?

    BUT it didn’t stop me!

    Now that the year has come to an end I can look back and say that I achieved what I set out to do 12 months ago.

    I started my own business.

    The plan was to start an agency that has the client needs in mind and not just our own profit. We wanted to help businesses by listening to them and creating a solution for the problems.

    I therefore agree with your post here.

    1. Michael, congrats on pushing through the negativity and working to achieve your dream, and congratulations on starting your business! I wish you a ton of progress in 2019. With your mindset, you can’t help but succeed!

Comments are closed.