When I was in high school, I saw myself becoming a genius, billionaire, playboy philanthropist.

I haven’t quite given up on that dream.

We all have this ideal image of ourselves.

And yet, most people never reach that ideal.  We spend a lot of time showing off on Facebook and Instagram, but in reality, we’re stuck.  We don’t know quite why, but we are.

It’s easy to talk about how we need a vision for ourselves and we need to dream big and set goals and so on.

The self-help industry rides plays on that opportunity to inspire without actually helping.

There’s a place for that inspiration, but it isn’t here today.  Instead, I’m going to show you something that will help you see exactly how you are moving towards or away from your ideal.  Or, maybe you’re just static.

I was never a big spender.  But, when I did spend…

I’d go for the $150 pair of glasses but never the $20 pair.  I’d buy the Armani Exchange rather than the Kohl’s special (Giorgio Armani was still way out of my price range).  I balanced this out with disciplining myself on the smaller buys — a $9 burger over a $16 entree.  (It adds up!)

In part, it was my ego.  In part, it was my vision and goals.  Remember, I wanted to be that genius, billionaire, playboy philanthropist.

But how I spent my money was largely unconscious.  There wasn’t a method to spending – I just based it on my mood, and occasionally rewarding myself.  Overall, I was frugal and hardworking.  But that may have only made it even easier for me to track trends in my spending

You’ll see I talk past-tense largely here.  That’s because I did this exercise back in 2012.

Here’s where you get involved and take action.

I’ll walk you through how I analyzed my spending to see if I was tracking towards my ideal, moving away from it, or staying static.

First, let’s assume you know your ideal.  Something more specific but just as enticing as a vision of being the genius, billionaire, playboy philanthropist.

Now, take out your credit card statements over the last six months.  (In other words, get into your online banking account.  Who really uses paper statements these days?)

If you’re a cash guy (or gal) like me, receipts will be helpful.  Hopefully you kept those!

In a simple spreadsheet, start listing out how you spent your money and in what context.  Track the purchase, cost, motivation/context, and anecdotes on what this may say about your personality and goals.

From this, I could see I spent some cash on fashion.  It was usually after some hellish weeks at work where I made serious cash as well.  (At least serious for me at that time.)


An entry from my spreadsheet looked like this:

  • Purchase: A/X Travel Bag
  • Cost: $120
  • Motivation/Context: Visiting NYC on a winter vacation.
  • Personality/Goals: Delving deeper into the luxury market I’ve been attracted to for years.  Ego-driven over functionality and frugality.  Helps me at least appear to be tracking towards my “success” vision both to others and to myself.

My main purchases were along these lines.  Reward myself with visual reminders of where I’m looking to move forward.

I wasn’t the smartest at investing in myself at this point.  What would have been better?

Purchasing a course to teach me about a skill I needed to learn, like copywriting or marketing to the affluent.  Or, joining a mastermind.  Or, saving that money so I could start my own business.

But hey, no regrets.  Doing this just let me see how I was spending my money.  I suppose I could have spent it on much worse anyhow.

I’ll give you a more current and less vain example soon…

How does this test compare to those fancy personality tests?

You know, they track your strengths and traits and all that.

You know, we answer them based on what we picture of ourselves and who we should be, but not who we are.

That’s why they’re usually useless.  We do this unconsciously and without malicious intent.  After all, we take those tests to help ourselves.

What much more authentically shows us who we are as an individual is how we spend our hard earned money.

It isn’t perfect of course, but it’s one method to assess yourself.

Or, you can stick to those personality and strength tests where we end up with results that we love to hear.  It outlines who we want to be and positions it in a way where we hear it like we’re already there.  We sit and listen to the results, nodding in agreement to every sentence.

Maybe that’s why we end up so addicted to taking these tests that tell us “who we are”. We just love the answers.

In reading legendary copywriter Gary Halbert’s “The Boron Letters”, Gary talked about this briefly. He asked a group of college students to raise their hands if they liked plays more than movies. Many hands rose up. Then, he asked who went to a play in the last week. No hands up. Then, who had seen a movie in the last week? Many hands back up.

People identify with who they want to be more than who they are. Some of it is for how we want to be perceived by others, but some of it is also how we want to perceive ourselves.

Want to identify who you really are?  (And A More Recent Case Study)

See where your money’s going.

Seriously, review your credit card statements over the last month. Think about where you dropped cash on the spot.

Here’s a breakdown of my main expenses for June 2014:

  • Sushi Dinners: $185 / 4%
  • Self-Education: $1,197 / 24%
  • Formal Education (MBA): $1,823 / 35%
  • Business Expenses: $328 6%
  • Home: $950 / 18%
  • Health / Supplements: $67 / 1%
  • Travel: $598 / 12%
  • Total: $5,148 / 100%

What does seeing where my money goes tell me?

First, I love education. I think that’s apparent.

Second, my cost for home is average, but could be much less. However, $950 is well worth living where I do because I love the neighborhood, the environment, and the townhouse itself.

Finally, I have some smaller expenses but they still show clear value to me.  Travel, sushi, and my health are priorities to me.

It’s great to see where I’m investing my money and how it aligns to my values.


But where don’t I invest?

$328 is a pretty small amount for my business.  Granted, this is just a single month and the education has correlation with ym business.  Still, I believe you need to spend money to make money.  That wasn’t something I put to action apparently last June!

What else does this lack of investment show?  I didn’t stick to my guns on outsourcing work that wasn’t high-value, high-leverage, and revenue-generating.  That’s a concept I strongly believe in, but didn’t invest in.  This has since changed since I did this exercise a second time in 2014.


What else is lacking that isn’t listed in my expenses at all?


Sushi and travel is huge, of course.  But that doesn’t quite count as entertainment alone.

As an anecdote, this doesn’t include getting together with friends and family and a free event I went to in this month.  Still, entertainment seems to be a major expense for most people, so for it to be completely absent is interesting – no?


But here’s how to analyze it.

It isn’t necessarily bad for me to not invest in “entertainment”.  Remember, it matters who we are, not what we are perceived as.

I’m happy with the level of entertainment in my life now.  Both who I am and who I want to be doesn’t include an entertainment aspect.  My need for fun and excitement is fulfilled by following my passions, self-education, and spending time with friends, family, and the amazing people I meet in my professional network.


Don’t judge a book by its cover.

The point to all this is: you have to dig deep to find your ideal self. You can get lost in what you believe you ought to be, or what others believe you ought to be. But don’t. Be conscious of those risks, and be aware. Proceed accordingly, and over time, your authentic ideal self will come to light.