How Confused Optimism & Money Disillusions Can Kill Your Dreams (+ A Simple Solution)

How Confused Optimism & Money Disillusions Can Kill Your Dreams (+ A Simple Solution)

confused optimism

“Why risk what you have and need for what you don’t have and don’t need?”

~Warren Buffett

A few weeks ago I was seduced…

I recently had lunch with a buddy of mine who finished business school and now is about two years into his investment banking career.

As we indulged in some Chipotle, he casually mentioned the kinds of salaries some of his buddies were getting and how he was looking forward to his massive year-end payout. Mind you, these are the type of bonuses that can buy homes (or perhaps even small countries). All he had to do was put in the time and he was all but assured the golden check.

That’s when it hit me.

Suddenly I caught myself thinking of how nice it would be to have what he ‘had’. The seemingly certain paychecks, the consistency – It all sounded so freaking awesome. For a moment it felt worth trading for.

Then I remembered how our lunch started…

He explained how out of the last three weeks he’d had dinner with his wife once. He had been at the office for around 12-14 hours a day (except on weekends when he was lucky to only work 9-5). And his workout routine was about as consistent as his family dinner appearances.

Many of his friends and co-workers spent 20% more than their monthly take – despite it being enough to buy that small country. The watches, the suits, the status, the dinners, the seemingly ‘necessary’ luxuries they’d gotten used to.

All this added up – to a price I knew I wasn’t willing to pay.

The dark side is often closer than you think.

The scary thing was that for a few minutes I was envious of the life my friend described. I actually started to think that’s what I wanted.

I’ve been there many times before – every entrepreneur, Living Legend or passion pursuer has.

And that’s how fast optimism can kill your dreams.

I took the one redeeming aspect I saw in my buddy’s career (the consistent money) and my optimistic mind managed to look past everything else about it that I knew I couldn’t stand.

People do this everyday, and without knowing it their selective positivity tries to convince them their own dreams aren’t worth fighting for. 

Luckily I knew how to snap out of it.

I am proud of what I do. I make a respectable living from it (still plenty of room to grow though ;). I get to help a ton of people (in areas where I feel I have unique talent) and I know there is no path I’d rather be on right now. Heck it’s a Saturday morning at 7:54am, and I am still in my sweaty running clothes because I could not wait to get to my computer to write this stuff down.

I have dinner with my wife almost every night. We take trips when we want and work on things we care about. We have time for our friends and have learned to cherish what’s important.

I love what I do.

It’s not to say that my buddy has chosen the wrong path – that’s only for him to decide. I just know enough about what matters to me to know it’s not worth it.

Doing work you love is freakin’ tough. No question about it.

Not only are we faced with the deepest and darkest fears, but on top of that we look around and everyone seems to have it figured out.

First off, they don’t.

Selective optimism is killing us.

We look at everyone around us and we only see the most enviable parts of their situation. The outward things that tend to show quite nicely – i.e. the fat paycheck, the big title, the overly liberal expense account, the secretary, the list goes on.

For some reason it’s so easy to find the things we admire about others’ lives.

Yet our outward optimism blinds us from what sucks. The long nights, the lack of freedom, the boss that treats you like you’re still in kindergarden or the work that makes you want to toss your laptop out the window.

We become so damn positive that suddenly we start thinking we want things that don’t actually matter to us, or even worse, that may cause us to tear our hair out.

It’s our own selective optimism that keeps us from pursuing our dreams.

The solution: Be optimistic with your own situation but realistic with others

Optimism can be the all powerful tool, as long as it’s not abused.

Have high hopes for yourself but stop trying to think you understand someone else’s situation. You don’t.

The paycheck is the easiest part. If you are smart, eager and willing to do whatever someone says and work your ass off, the paycheck will eventually be there.

The real challenge is: does the work required to get the paycheck make you happy?

You get this right and it’s worth even the biggest claims of fame, fortune or whatever the seduction of the day is.

There are two sides to every story.

Our natural (and very dangerous) tendency is to only see the things about others’ lives we’d like to have…especially if our own life seems challenging at the time (such as when searching for the work that matters to us). Our glasses are rosy as could be.

Be warned – you are not seeing reality.

Some of you look at me in a similar way.

I know because I get notes, comments and coaching inquires asking me to help people build what I’ve created. It’s flattering and humbling. But don’t be misled. I don’t have everything figured out either. Not even close. I have my fair share of moments where I have no idea what or how I’m going to solve the next problem. Where I panic. Where I question decisions.

We are all learning as we go. That’s the fun of it.

Stay in your own experience.

Have your own deep reasons for why you want what you want.

That way others won’t be able to throw you off.

Next time you find yourself envying those around you, ask yourself the following:

Do you need what you think you need?

I bet you could be happy on a lot less.

Do you even want what the others have?

Hard to know if you only pay attention to the good stuff.

Is it really worth the trade off?

I bet it’s not.

Beware the seduction. 

If you let it control you too much, you’ll end up in the most dangerous scenario of all: doing work you don’t like to make money for things you don’t actually want or need.

Stay there long enough and escape starts to feel impossible.

That’s why Live Your Legend is here. That’s the purpose of this community – to support you in making that escape.

There is no journey more daunting than the one to doing work that matters. There’s also nothing more rewarding.

You will be challenged. It will be tempting. The grass will look greener.

Just remember: It’s usually not worth it. 

The only path worth walking is the one you create for yourself.

The grass is never greener than it is on the path to doing things that make you come alive.

When in doubt, just keep walking.


But what if the money’s a real problem? – Here’s a solution. 

In last month’s ask the reader post, one of your biggest pain points was money: “my expenses are too high”, “I won’t be able to pay my mortgage or car payment”, “I can’t make enough money doing work I love” and so the list went on…

I respect how big of a topic this is and I want to help.

There’s no question, money’s powerful, money’s influential and money can be downright seductive. But, contrary to common sense, the pursuit of it is the very thing that can keep you from your dreams. The things people do to get more of it blow my mind – either through big-salaried jobs doing work they hate or through getting deep into debt to feel like they have more to spend.

One of the biggest reasons people don’t pursue their dreams is because of money.

Either they think they need too much of it or their debt’s taken up all their breathing room.

For many of us, doing work we love does not start at finding your passion and figuring out how the hell to make money from it.

It starts long before – with getting yourself out of the consumption and debt-filled hole you and society have buried yourself in. Only when those fears of survival are dealt with, will our mind have the energy to find the creativity and courage to live on passion.

Money fears and challenges are passion killers.

Clear them out and sky’s the limit.

Time to get started!


Images courtesy of Shandi-lee & steve_steady64