The illusion that's making you miserable

Setting goals is important. But achieving them won't make you happy.

I. Four Minutes of Happiness 

The $200,000 wire was on the way to my bank account. I’d just gotten off a call with the Swedish investor who’d set it up. “Yes, that’s how you spell my name,” I repeated, “And yes, that’s the correct amount of money.” It was old school. I couldn’t do it online, it had to be by phone. But it felt good, like saying it out loud made it more real somehow.

I’d spent the last few weeks pitching my startup to multiple investors. I’d secured cash from a few smaller angel investors and had recently caught a ‘bigger fish.’ It was a small amount of money, relatively speaking, but it would give my early-stage startup a few months of runway to survive.

The money was validation. It validated that we were on to something. That someone believed in us. That the dozens of rejections from people who said — in no nicer words — that “you suck and will fail” would be proven wrong. That the late-night calls with co-founders and the risk I took by using part of my savings and the emotional burnout that ensued shortly after would all be worth it.

The wire hit the bank. A smile covered my face and I yelled a loud “YES!” I felt relieved and confident and validated.

And then, the moment passed. As quickly as it had arrived, the feeling was gone. 

If I had to guess, I’d say that I was happy for about four minutes. 

Now what?

The feeling morphed into dread and anxiety. The next realization hit my stomach like a sledgehammer. Fuck, I’ve got a lot of work to do now.

II. The Alchemy of Hardship

I love setting goals. Goals to raise money, to run marathons, and to be a better writer. This pursuit of happiness has made my brain hurt, required frequent trips to the chiropractor and begged the question from my wife, “What the fuck are you doing?” Yeah, sometimes I gaze out my window and wonder, is it all worth it? The answer is Yes. Challenges keep me inspired. Even when I don’t reach the top, my goals push me to new heights. They make me a better person. 

When I ran the Mt. Fuji Marathon (lots of uphill!), I found it extremely motivating to think about what was waiting for me at the finish line. Namely, a bowl of oily ramen noodles, an ice pack, a kiss, and the feeling of saying ‘I did it’. When I stopped to rub my aching knees and curse the universe, the anticipation of these treats kept me energized. Just putting one foot in front of the other wasn’t enough.

To be the best version of yourself and fulfill your true potential, it’s not enough to just “go with the flow.” Sure, sometimes you can forget about the goal for a bit — so you can focus on the task in front of you — but if you don’t remind yourself of the goal often, or if you lack the goal in the first place, you’ve created a recipe for failure. While it sounds nice to say que sera sera, I’d be hard-pressed to name an athlete or entrepreneur or inspirational leader that didn’t obsess over a very specific goal. Gandhi was all for world peace, but his front and center goal was Indian independence.

In Viktor Frankl’s Man’s Search for Meaning, he had a god-awful time being locked up and starved in a concentration camp. Unimaginably so. Much harder than running a startup or the Mt. Fuji Marathon. But he didn’t lose hope like many of his fellow cellmates. The reason Frankl kept going, his motivating life-force, was his unwavering desire to finish his book upon getting out of Nazi hell. The goal to write a book kept him alive! Without that inner fire, we probably never would have heard his inspiring story.

The point is, your dreams and goals drive you to take action and keep you going. You need them! When you set a clear goal, you structure your way out of hardship, or at least hold on to some shred of hope. The result is alchemy. Your gritty, messy hardship transforms into beautiful gold (success) through applying your will-power in the form of goal setting. When you have a clear Why, you can achieve anything.

III. The Goal-Setting Paradox

But. But. But. 

Then the moment comes when you actually do achieve a goal. It usually feels good, like when I got the $200k in my bank account. And then the moment is gone. Vanished! Kapoof! Just like that. Then you have to continue living in the next moment, which isn’t necessarily full of rainbows and cute puppies. Jack Kornfield states this beautifully when he says, “After the ecstasy, comes the laundry.” 

When you try to hold on to that moment for too long, it’s like trying to wrestle an eel. It’s animal abuse, and the eel always wins.

When I hit my fundraising goal, the reality of what that really meant suddenly hit me. Yes, we had the cash, but it also meant that I had to hire more people, work harder, and since it wouldn’t last long I’d have to start thinking about the next round of funding already. The goal post immediately shifted to a new one further away. I’ve felt this repeatedly, without fail, for almost every goal that I’ve set in my life. 

The paradox is this: Goals can be very motivating, but when you reach them happiness doesn’t last for very long. 

Is it possible to strike a balance of healthy striving for a goal and find happiness in the process? Yes, I believe it is. 

IV. Deconstructing the Myth of “Getting Somewhere”

Psychologist Carl Rogers talks about seeing yourself as an ever-changing process and not a “finished product” in his book, On Becoming a Person. When a client comes in for therapy they typically want to achieve a fixed state: to reach a point where their problems are solved, where they’re more effective at work, or where they have a happy marriage. 

As the therapy continues and they feel more freedom to express themselves, they tend to drop some of these fixed goals and realize that they’re not a “fixed entity,” but are constantly in a process of becoming something. And that’s when the real therapy starts. 

Rogers, who counseled thousands of people, says people seem a lot more content in their lives when they take this perspective. Here’s his description of what it’s like to accept oneself as a “stream of becoming,” rather than a finished product: 

“It means that a person is a fluid process, not a fixed and static entity; a flowing river of change, not a block of solid material; a continually changing constellation of potentialities, not a fixed quantity of traits.”

If you’re confused, here’s a more specific example. In the last hour of writing this newsletter I have felt all of the following  — excited, curious, frustrated, upset, peaceful, stressed, hopeful, uncomfortable, tired, sleepy, confused, hungry, anxious, fuzzy, irritated — and the list goes on. I’ve had many feelings that are in a state of constant flux and flow. So to say that I am just “happy” today or “anxious” isn’t the whole picture.

This way of looking at yourself as constantly changing is a choice, and it’s very counter to how the media and society have taught us to think. Usually we like to give ourselves a label or ask a big, looming question like, “Are you happy?” But the answer is not Yes and it’s not No. An honest answer would be more nuanced that takes into account the fact that you experience a lot of different feelings throughout your day. 

When you try to cram and twist your experience to fit your preconceptions — “I should feel this way or that way,” you pigeonhole yourself. You trick yourself into believing that a certain number in your bank account or that quitting your job or reaching a higher rung in the hierarchy will bring a fixed, permanent feeling. But that's like when you take a train from platform 9 ¾ and arrive at a magical land where the rules don’t apply. It’s a fairytale. 

V. Are You Pursuing Your Goals, or Are Your Goals Pursuing You? 

Do you find yourself saying the phrase, “I will be happy when ___?” That’s your first sign that you’re falling into the trap. You are chasing an empty pot at the end of the rainbow. It’s an illusion, and it’s making you fucking miserable. Why? Because we know that you'll just continue to create more and more goals. So if you can’t be happy now, with what you have and what you are, then happiness will continue to elude you.

What if you could flip this idea on its head and find a way to make life effortless — for a goal to pursue you, and not the other way around? Well, it’s possible. The Sufi poet Rumi once said, “What you seek is seeking you.” He didn’t mean that there is some external “thing” out there looking for you. I take it to mean that your desire for happiness and joy are not going to be found by constant problem-solving or chasing or achieving any goal. True freedom, perhaps, is going to come to you when you accept that there is no fixed state called “happiness.” And when you do, it never has to feel like you’re chasing something.

What You Seek is Seeking You – Rumi

You can think about some of your fixed goals and reframe them as more of a fluid process. Having a happy marriage becomes ‘a marriage that is continually improving.’ A startup with a certain amount of money now becomes ‘a startup that is shifting and constantly finding new ways to grow’. A career with a certain title or accolades turns into ‘a career that is constantly evolving’. All naturally come with ups and downs, ebbs and flows, inching in a direction that feels right.¹

When you’ve realized how silly it is to believe you’ll be happy when you get somewhere, you remove a lot of the tension in life. This leaves you with a sense of flow for whatever you are doing. And that’s really enjoyable. Of course, depending on who you are, some things are just more fun than others. There’s an ongoing process to discover what we intrinsically enjoy, and that’s a journey every person has to make on their own.  

VI. The Key to Happiness is to Stop Believing It Will Last Forever

Fixed points are an illusion. You’re never finished and you’ve never arrived. Your work is never done. In other words, lasting joy and happiness doesn’t come from explicitly reaching a goal. It has to come from what you are doing right now. Let go of the outcome and focus on what you can control – the process. When you’re not preoccupied with thoughts of the future (or the past), you’re more likely to be in the present moment.

You can choose to get disappointed waiting for a feeling to last. Or you can move on with your life with a smile and shift from thinking that this feeling is supposed to last to that of reality: life is one, big unfolding and constantly changing process. You will still feel anger, frustration, anxiety, and your butt will still itch no matter what heights you reach.

You can have new goals or milestones and you can be inspired by them. But when you’re at the next point, it’s not that “this is it,” but simply that “I am a different person now.” There is always room for growth even if it’s in a direction that you can’t currently imagine. When you look at it this way, you can continue to become something without ever feeling like you have to stop. 

Pick a goal and move towards it. But know that when you reach it, it’s not going to make you permanently happy. And from that point onwards, know that you will continue to change and to become someone else until you get to the next point, ad infinitum. Or, until death, but that’s just another type of change isn’t it?

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Discussion topics and questions to ponder:

• What “fixed points” are you most attached to in your life? 

• Can you remember a time when you did something without setting a goal (like a hobby, for example)?

• How can you change some of your fixed goals into thinking of them more as a fluid process? 

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Let me know what you thought of this week’s newsletter and drop a comment below! 

1. So, should all of your goals should be reframed as more impermanent, flowy, ever-changing things? No. There are different types of goals. The answer is probably a bit of both — there are some goals that could use a higher-level reframing (“I want a happy marriage” is too static and “I want a marriage that is continually improving” is probably going to destress you, to Carl Rogers’ point) whereas “I want to make $200k for my startup” is a very specific and perhaps necessary goal for survival; rather than changing the goal itself it would be more about changing your relationship to it so you’re less attached to the outcome/not tying your self-worth with the result.