There is a good chance the pursuit of future success is costing you the experience of happiness today. 

In the past two weeks we have explored Tim Ferriss’ 17 questions from Tools of Titans to test the impossible. We covered doing the opposite and scratching your own itch. Now let’s turn that on its head and evaluate if we should even be trying at all. Some of these ideas may seem contrary to my recommendation to live a life of planned intent and growth. I will explain how it all comes together to yield the best version of you possible. 

“Question 3: What would I do/have/be if I had $10 million dollars? What is my real TMI?”

At the time he discovered this question, Tim was achieving a high financial measures of success but it came at a cost of well-being. He used this question to evaluate if his course of action was as valid and necessary as he thought. This wasn’t a visualization exercise intent on galvanizing his fervor for success. It was a momentary pause to see if he had unknowingly already achieved successs.

Is Your Passion Authentic?

There is a thing in personal and professional development where it becomes cool to be the most open-minded, self-aware, constructive person in the room. It’s probably a throwback to our pack mentality that we don’t like being different. Even people who pride themselves on being different gather in packs of people being different (I’m looking at you hipsters). They generally don’t realize that being anti-establishment is itself a pro-establishment. 

I find this often leads to an inauthentic engagement and representation of one’s opinion. People saying what they think they are supposed to say depending on the narrative to which they are trying to be true. If the group is talking about being driven and motivated most people will join in the call to arms. In the wake of this communal passion, someone in the group will be experiencing frustration with their lack of that quality and begin to be really excited about getting better. However, inevitably and appropriately, someone eventually says “but we don’t want to get TOO driven and motivated that it causes bad things to happen”. Immediately our “I want to be more driven” person flips to say “oh yes, I should take it easy on myself.”

This isn’t a problem. Like I said it’s human nature. We are remarkably binary. Unless one has developed the very valuable skill of tolerating ambivalence, we either join in loving something or join in hating it. Marketing companies take advantage of it every day. Our current political climate is rife with it. If someone wanted to bring back platform shoes with a goldfish in the heel (Disco Stu-style) they absolutely could do it. If we see lots of people doing or saying something we naturally want to regress to the mean. We develop a sense that we should want those things too. 

It’s also the basic structure of why mediums like Twitter, Instagram, and SnapChat work. It’s why MySpace faded and Facebook evolved away from it. When “the cool thing to do” was only dictated by our Top 8 friends, social media had little societal value. It had individual value. If I needed to know what to wear out I didn’t take to social media to check the pulse of fashion. Instead I messaged one person in my Top 8 to get advice. Or I called them (remember we still had telephones back then). Now if I want advice, why limit it to my one trusted friend when I can see what tens of thousands, maybe even million of people like. Again, pack mentality allows us to drive our preferences toward the mean. The most effective way to stay in touch with those millions is via short burst social media engagements. Add in some pictures, a few celebrities, and BAM! you have a species trained to dictate their future behavior by constantly utilizing a data stream presented in the form of text and images (that’s actually all social media is).

Don’t Drink the Kool-aid Unless…

Okay, that seemed like a huge digression. It was. My point though is that I feel very strongly that all people who promote a certain path should take opportunities to offer their followers an alternate experience. Don’t follow us because we represent the masses. 

This goes back to the value of doing the opposite. All the aspects of our lives that bring us pride are heavily biased by that very opinion that it is a good idea. We drink the Kool-aid because someone showed us how and “that dude knows how to make Kool-aid”. Take time to consider what Sunny D might taste like. Or better yet, try some of that “purple stuff”!

We have to check our assumptions from time to time. I like Tim’s use of fanciful, seemingly unrealistic prompts to explore a blindspot here. It stimulates thought. Let’s assume you are in the process of pursuing a goal that will provide you with more money or a better lifestyle. You are essentially doing everything we’ve said in prior posts is a good idea to have onboard at all times. Good job! However by asking yourself what you would do with $10 million dollars in the bank you are saying “if I woke up tomorrow and no longer needed to grind and chase what would I do with my life?”

He compares this thought exercise to retirement. For many people they are working in hopes of providing for today and to create some future life where they stop working. Retirement is actually a dangerous developmental trend I don’t have time to get into here. Let’s leave it at this: the mythology of what awaits us in old age does a great job of guaranteeing we fulfill the prophecy of declining function. However, how many retired people or even those who finally achieve their goals stop and say “I wish I’d smelled the roses more. Taken it slower. Been happier along the way”? It is actually one of the more common sentiments of the Titans Tim interviews on The Tim Ferriss Show. It doesn’t seem to be as emphatically represented in the book. 

You Want Less Than You Think You Do

If you had $10 million would you put it away and keep grinding until you are 65? Probably not. When you answer this question of what you would do if you retired today with unlimited funds you will outline what you actually wish you were doing today. Tim and I will sell big on the idea that the reality of what you want today isn’t as fanciful as you assume. You may say “travel every day” , “eat at a new restaurant every night”, “sleep until 10am and swim in the ocean daily”. Great. I love those ideas! 

Odds are that they are a romanticized version of what you really want. If you’ve ever taken a stay-cation you likely have experienced something closer to what your natural “retirement” lifestyle will look like. I don’t imagine your idealized retirement involves binge-watching Orange is the New Black or playing every game in the Call of Duty cannon. “No way man, I won’t let that happen to me when I’m old. I only veg out on stay-cations because I work so hard I need that time to recover.” Excellent. I love your optimism. I’m glad you feel confident that the old version of you with decreased muscle strength, range of motion, balance, visual acuity, and executive functioning is going to outstrip the tenacity of young you. Oh and “sleep until 10am” when you’re 65? Go call your grandpa and ask him about that. 

Don’t Make Choices Today at the Expense of Tomorrow. 

Today is temporary. Tomorrow is constant until it becomes today. Never make a choice that will cost future-you without careful a thorough cost-analysis. Don’t commit to a lifestyle change for today that you will suffer for later. It’s a basic tenet of finance, athletics, and development. Play the long game. 

I think it is important that the Growth Mindset, goal-achievement-machine version of you regularly test if it’s time to walk away from the table. Maybe it won’t be time to exist, but if you never stop and ask yourself “is this good enough” you will be guaranteed to miss it when you’re there. Don’t burden your future self with regrets. 

What Does Happiness Cost You?

This is where Tim emphasizes the role of calculating your Target Monthly Income (TMI). You have asked yourself what life would look like if you retired today with plenty of cash. Now take that lifestyle and assess how much it costs per month. The goal is to see if you are actually already there. 

I knew a guy who was very, very simple in his needs. A comfortable home. A second house at the Jersey Shore. A good delivery pizza place. A low key, cheap bar within walking distance. Maybe the occasional baseball game or night out with the guys. Once or twice a year he’d make a splugy purchase under $2000 to treat himself.

Let’s run his TMI. The rent on his home would have been about $1700. The Shore house, probably $500 a weekend including travel and food. Add in static expenses and a budget for his splurges, I’d estimate he could get by on $4k net income a month. Max. 

If this person decided to focus on happiness instead of hustle, he should put all effort toward finding a job that gets him $4000 in as few hours as possible. Alternatively, if he is making over $4000 a month he needs to be damn sure that every dollar over $4000 is worth the effort. He has already decided he doesn’t actually need it. Dream retirement is in his hands already. 

Another way to look at it is that for every $48,000 he can create in assets he buys himself a year of retirement. Want a year sabbatical? Plan out how to set aside $48,000. Want a month instead? Set aside $4000. It’s all that easy. 

Knowledge is Wellness 

I am not saying everyone should go out and quit their jobs, move to rural America and call it good. That won’t be for everyone or even most. I am also not saying that calling an end to the grind is in your best interest. However I am emphatic in people being able to confidently say “my life is the way it is today because I choose it to be so, I know what else I could pivot to right now and I know I don’t want it because I have tested it.” I think that statement may be one of the most valuable goals a person can have and is a consistent part of the people I meet who are doing well. 


As you can see by this very long post. I love this question. What is the dream life for you and can you regularly assess if you have actually achieved access to it? By calculating your target monthly income you can go from ambiguous fanciful dreams like “travel the world”or “retire by the beach” and turn them into a hard dollar amount you need to chase. Each dollar you increase your monthly income the closer you get. Maybe you find your current career will never offer than target income. What do you do then? What impact would that knowledge have on decision making? Self-exploration can come at a cost and it is very vulnerable to generating a manipulated product of who you are. However, exercises like these, when done with care and transparency, can offer immense value to sustainable wellness. You may be able to “buy happiness” today. 


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