Written by
Michael Wells


Why chasing happiness doesn't make us happier

Written by
Michael Wells


Why chasing happiness doesn't make us happier

Written by
Michael Wells
What I've Learned

Everyone has a Happiness Plan for their life..._
But most people don't succeed in finding that happiness, especially on the first try. Here's where things go wrong, and what happens next.
You can learn a lot from the lives of others._

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This month, I’ve reached my 450th coaching client.

Pretty cool eh? I think so. For something that started as a hobby, I really enjoy that coaching has become such a deep part of my life.

Every 50 clients or so, I feel like I need to step back for a bit and reflect on what I’ve learned. Each client I have teaches me new things about people and how people view their problems- and the more clients I work with, the more clearly I can see the patterns across the problems that all people share.

I think of this as the "modern human experience," and recently, my insights are shifting yet again.

At the beginning of my coaching journey, I saw things more at the individual level- how people relate to their problems, the type of things they identify as problems, and the emotions they struggle with.

There were lots of patterns there.

At around 250 clients, my view expanded and I began to see similarities in how groups of people think and how they experience life. People with similar childhood experiences and family structures often share similar problems.

Cultural background has a tremendous influence in our sense of "normal" and the things we prioritize as problems. People from strong religious backgrounds also often share similar struggles.

Men often share problems like stress, depression, despair, and social anxiety. Women often struggle more with general anxiety and subtle relationship dynamics.

Patterns are everywhere, and they’re incredibly consistent. They are so consistent that if you tell me your family background, your cultural influences, your gender-identity and major life experiences, I can usually guess your top 3 life challenges.

It's not magic. It's based on one simple observation.

At the core, everyone wants the same thing.

The happiness plan

Everyone wants happiness, and most people seem to think that right now, they don’t have nearly enough of it.

Most people see themselves as travelers who are "on the road to happiness." They are certain that they know exactly where to find happiness, but they're not there yet... and traffic is a bitch so they're not sure when - or even if - they'll arrive.

They think they are unhappy because there is a specific thing missing from their life. Money. Self-confidence. Sex. A perfect relationship.  Or, there is something in the way of their happiness that they do not know how to escape. A difficult boss. An unhappy relationship. Parenting struggles. Finance struggles. Low self-esteem. Depression, or anxiety.

Whatever it is, they imagine that if they could fix this one thing, life would be perfect.

And they have a plan on how to reach that place.

I call it the Happiness Plan.

That plan might involve finding The One, building social confidence, a great career, a successful business, starting a family, or becoming rich or famous...

Whatever it is, they’re 100% certain that this is the thing they need to be happy in life- and that they absolutely cannot be happy without it.

But life rarely goes to plan.

When Plans Fail

"Everyone has a plan, until they get punched in the mouth." - Mike Tyson

Sometimes reaching that life destination is harder than you imagined- especially when the plan depends on other people or circumstances that are outside of our control.

And for people who reach their goal, the grass isn’t always as green as they imagined it would be. Just ask the 50% of people who follow the marriage & family plan, and end up divorced.

When plans fail, I see one of two things happen;

  • Some people try the same plan again. They repeat the exact same plan over again, in hopes it will work a second time. This happens most often when someone thinks the plan was derailed by outside circumstances. They imagine that other people or circumstances were the problem- but the plan itself was perfect.
  • Some people abandon the plan. They make an entire new plan, usually radically different from the original plan.

And this plan, fail, and plan-again process happens more than once. For most people it happens many times, and there’s an important cycle, and a pattern attached to it.

Why Plans Change

After 23 years of coaching, I’ve worked with people in every phase of life. I’ve had clients who are teenagers, I’ve had clients who are retired, and I have clients everywhere in-between. More than 80% of my clients fall into two noticeable groupings- late 20’s to mid-30’s, and mid-50’s to early 60’s.

I don’t think that’s accidental.

These are two consistent timeframes in life where people seem to feel stuck. Their happiness plan has failed, or it "succeeded" but it isn’t delivering happiness, and they are not sure what to do about it.

They feel stuck, and unable to be happy.

So they reach out for help.

The Cycle of a Happiness Plan

Let’s zoom out and look at a modern human life. Here's what I see.

Ages 14 - 21 - Teens and young adults are stressing about the plan, trying to define it and figure out what the road ahead is. What education and career should they pursue? Should they date or get married? To who? When?

Ages 21 - 28 - are full-on executing The Plan. They’re dating like mad to find The One, or they’re studying and working like mad to build The Career. Or, for the artists, they’re powering through long days of developing their craft - whether it’s sports skills, art skills, music...

Ages 28 - 35 - disillusionment & plan adjustment. They’re trying to adjust The Plan to make it work. Maybe the relationship doesn’t feel the way they imagined, or maybe it has problems. Maybe parenting isn’t what they imagined ( it’s tough ). Maybe the career is a tough slog at the coalface with little sense of progress.

Ages 35-42 - major adjustments happen. Divorces, career changes. People quit their jobs and start their own businesses. A New Plan is developed and they're back at the coalface grinding away to make it work.

Ages 42-49 - disillusionment & plan adjustment. Also known as the mid-life crisis. Many still haven’t found the success they wanted, and the happiness they imagined with it. Even those who were successful in their plan often feel like the promised happiness really isn’t there. Life is boring, or missing something. Maybe they need an affair, or a new hobby like golf or scuba diving.

Ages 49-56 - new major adjustments. Divorces, career changes, move to a new country, start a new business, become religious, or abandon your religion... Another New Plan is in place, and this one will work.

Ages 56-63 - disillusionment & plan adjustment...

Obviously, these timeframes are not set in stone, but I see a remarkable consistency here. Notice where the most common "stuck points" fall- they align well with some of the most stressful periods of life.

  • Teenage angst, when kids are confronted with major decisions that they need to make about their own future.
  • Midlife crisis, when even successful adults feel like life is failing to deliver happiness.

And a third area that I think is often overlooked-

  • The period between ages 28 and 35, where I have a lot of clients stressing about relationships, careers, and parenting. In this period, people often feel like they are at the very edge of their limits in dealing with it all.

Uncertainty and decision making are stressful, it would seem.

Understanding these cycles is very important, but let's shift our focus back to the plans themselves, because there is a lot to learn there.

What I’ve learned about happiness plans

These are the most interesting things I notice.

Plans have types

Happiness Plans typically take on one of several flavors.

  • Relationship = happiness. For most people, this plan comes in the form of a romantic. exclusive, long-term commitment, preferably involving marriage, living together and shared assets. For others, it’s about family relationships, or key friendships.
  • Children = happiness. My life needs meaning, someone who needs me, and a kind of genetic immortality. Family and legacy are everything.
  • Fame = happiness. If others like me, I can like myself.
  • Fortune = happiness. If I have no financial stress and the freedom to have whatever I want, I can be happy. Wealth is power, and security.
  • Opus magnum = happiness. By this I mean a particular form of self expression, like writing a book, a symphony, an artwork. For some people this sense of purpose and fulfillment is the one thing they crave most.
  • Adventure = happiness. The travelers, adventurers, extreme sports enthusiasts- the people who want to taste the whole buffet.
  • Self-conquering = happiness. Overcoming inner struggles of social anxiety / depression / general anxiety / low self-esteem. If I can free myself of my demons, I can be happy.

In some cases, people mix and meld these fundamentals into their own plan- for example, the Career success plan can involve fortune, fame, and opus all together as motives. People who embrace polyamory as a lifestyle are sometimes looking to meld adventure and relationship happiness plans.

The First Plan is borrowed

Your first plan is typically not informed by much personal life experience, so newly-minted adults in their early 20s tend to apply the plan that their parents, culture, and friends handed them. It becomes The One True Plan, and they rarely doubt it, until it fails to deliver.

Obviously, that’s influenced by their major childhood experiences as well. If you saw your parents have a terrible relationship, you’re much less likely to assume that the Relationship Plan is your best path to security and happiness.

Plans have a shelf life, and a use-by date

Every Happiness Plan has an expiration date.

A plan generally has about 7 years to prove itself, before people give up on it. Even if you reach your goals, you probably need a new or adjusted plan to course correct your life towards your goal of maximum total happiness.

Major life changes reset the clock

A plan can be disrupted at any point, and the clock reset. If you followed the marriage = happiness plan, and your partner suddenly left your plan for whatever reason... then you will suddenly feel derailed and in need of a new plan. It doesn’t matter if you’re 22 or 54- the clock will reset.

In fact any major life change seems to reset the clock. If you begin a major relationship that has long-term expectations attached to it, the clock is reset.

I think it's no coincidence that the 7 year itch is a thing in relationships. At that point, if the relationship isn't delivering what you expected, you'll be doubting its ability to deliver what you "need" in your life.

Plan failures can be traumatic

At a personal level, a plan change is a Major Life Event.

When that change happens as a result of the "failure" of the plan, it usually comes with a lot of emotional distress. Sometimes there is years of emotional processing, anxiety, depression and therapy.

Our story about WHY a plan failed is crucial

When a plan is disrupted from the outside, many people will blame those outside circumstances and cautiously try to execute the same plan again.

The reason is that they identify the reason for the plan failing as being someone else. You see this a lot with second marriages. If you feel your first marriage failed because you chose the wrong partner, you will still believe marriage was the right plan, and you will just try to choose more carefully.

Sometimes, it’s clear that the plan itself is unreliable as a path to happiness, and people will pivot to an entirely different Happiness Plan.

In extreme cases, these Plan pivots can involve an element of overreaction. Eat pray love. Start a new life, change countries, begin a new career and relationship. Change your religion. Even changes to sexual orientation,

The key lessons

From a psychological perspective, the plan is an interesting thing. because it’s entirely based on fantasy.

We even absorb fantasy as a key ingredient- which is why Disney is such a problem. Young children deeply absorb the romantic love = happiness formula into their plan - without much understanding of the challenges, commitment and sacrifice that a real relationship demands.

Most plans seem to depend on other people and outside situations that are outside of our control. Part of this is the mistaken belief that happiness comes from outside of us, and that we depend on other people or circumstances in order to feel happy.

That’s a pretty fragile way to live. You might experience moments of externally-caused happiness in your life, but even if you’re a king and can exert a huge amount of control over your immediate world around you... how happy are you really?

If Game of Thrones is anything to go by, most of them are pretty miserable cunts.

There is a better approach

A plan is a powerful thing. But it helps to have a clear and honest perspective on your plan in order to use it effectively.

The best plans are the ones that are held loosely.

A plan is useful as a map. But if you find the bridge washed out, or a blizzard hits, or you discover a perfect homestead along the way, change the plan.

People often derail their own plans.

It’s very important to distinguish between a plan failing, and tasty distractions from your plan. One example is when someone following the marriage & family plan meets someone they are attracted to, who they imagine they might be happier with.

Immediately there is an internal conflict. They’re executing their plan, and have made quite a few commitments to it that others are depending on. But the dopamine system sees a new possibility, and it will try hard to sell you on the merits of this new opportunity.

Will changing partners really make your life that much better? What are your responsibilities here? What are the consequences of jumping ship?

Beware of your reptile-brain tendencies. Instant gratification is a powerful temptation, but if your goal is life happiness, it can derail that terribly.

Every plan goes through phases.

They follow a curve, like this;

  • Excitement about the plan, which is obviously the perfect way to build your perfect life.
  • Commitment and enthusiasm in executing the plan
  • Focus as you grind away for a few years
  • Exhaustion as you run out of steam
  • Frustration, as the plan is just not yet returning what you invested into it
  • Anger, resentment, sadness
  • Disillusionment... the plan is not working

People often wait until the resentment phase before they start making adjustments. It needs to happen much earlier, at the first hint of exhaustion.

No happiness plan lasts forever.

By definition, a happiness plan is about delivering a consistent emotional experience. But even when it works, emotional experiences never last forever. Even the most perfect happiness plan cannot always deliver happiness.

People don’t often see this, and go from a happiness high ( new job, new relationship, new family ) to a place where they are feeling “tired and slightly bored”.

There is no surprise here. How long did your new iPhone make you ecstatically happy? If you could have your favorite steak and lobster dish every single day... how quickly would that meal lose its appeal?

I'd give it a week, max.

We're just wired that way. Once we get that thing we really wanted, the dopamine just isn't triggering anymore.

Yet... we imagine the rules are different with the big life things. True love means ecstatic mad happiness with every breath forever, right?

When that doesn't happen, we begin to feel unsatisfied and want something more. Something must be wrong. Our relationship isn’t working right. Our partner isn’t doing enough. The kids are 5% sweet, and 95% exhausting. Our job isn’t with the right company.

I've found it's important to understand that, and to keep your expectations in line with reality. A garden is a fantastic thing to have in your life, but the weeding and watering can never stop, and the mosquitos are just part of the deal.

Expect those inconveniences and you'll enjoy the strawberries even more.

A successful plan does not guarantee happiness.

Again, just ask the 50% of Americans who follow the marriage & family plan, and then end up divorced and miserable a few short years later.

My favorite example here is rock stars. Everything in their happiness plan- fame, fortune, the adoration of fans, unlimited sex... they have every ingredient most people would want.

But are they happy? How many of them self-destruct with drugs, alcohol, and even suicide?

Too many times I see the same dopamine system that drove them to chase these things leave them unsatisfied- and ultimately result in self-destruction.

Plan away, but enjoy now, too.

Never expect your happiness to come “someday, when...”

Make sure you are happy now, and make sure to enjoy that happiness now. Invest energy and time in your hobbies, yourself, and your personal interests.

If you are spending all of today's happiness in the hopes of that "big win," then you're just playing the Lotto, and you are bad at math.

Don't waste your life. Today is at least as important as tomorrow is.

Make sure at least some of your plans are within your circle of control

Make your biggest investments in plans you can succeed at all by yourself.

Invest in your social skills and close friendships at least as much as you invest in your romantic relationship. You may need them, and they'll benefit and balance your romantic relationship too.

Invest in developing your expertise in specific skills, more than you invest in one particular job with one particular company. You don’t control that job as much as you think- but you can control your job-market value to a much larger extent.

Plus, if your life plan depends on finding The One... well, waiting for others sucks. Don't let that be your only plan.


At this point in my coaching journey, the thing that stands out to me is not only the patterns between clients, it's the gaps - the categories of humans that I don't see often asking me for help.

That's why I first noticed the life phases and the 7-year cycles I've described here, but there are other missing categories as well.

A key one is this- I have very few Buddhist clients. Roughly half of my clients are Asian, and yet very few are Buddhist. I sense that there is something important to learn there, and I'll pose it as a question-

Should happiness even be the goal?

To most modern humans, happiness is the fundamental goal of life. If we succeed at life, we'll be happy, and if we we're not happy then we've failed somehow. We also expect that if we follow the right path, that we deserve to be happy.

After all, we paid our dues, right?

This mindset dominates modern cultures but it's especially fundamental to groups such as modern Christians, who equate "right behavior" with reward.

But not everyone shares that perspective.

To some people - Buddhists in particular -the expectation is different. Suffering is the normal state of life, and joy and happiness are the special treats that might occasionally surprise you.

In the end, this difference in expectations gives them a kind of contentment and peace in their lives- a baseline happiness that I don't see in many of my clients.

To many of my clients, their happiness is conditional, and it's conditional on things outside of their control.

That perspective is a choice, and every choice has consequences.

At the very least, it's worthy of some deep personal reflection.

. Last updated on 
June 5, 2023

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