Why Your Stupid Goals Never Get You What You REALLY Want

And here comes a young man filled with stupid promise . . .


Many years ago, I was young. I walked into a financial planning office without an appointment. I wanted to invest 20% of my income. That was my goal. At 16, living at home with a part-time job, it was feasible.

“You keep this up,” said the woman at the desk. “And you are going to become a very rich man.”

The woman was so happy for me. She watched me walk out the door into the bright street. I could feel her hope.

I did become rich. I had 3K in investments by 18, which I spent in one drunken college summer, with the vague plans of returning to my goal of 20% after I started making 100K with my university degree.

That was a dumb goal.

Since then, I’ve become better at setting goals and actually reaching them.

The key to getting what you want is really accepting tradeoffs.

You see, last year I was trying to write a novel and write music and practice singing and write new songs and also write non-fiction.

I had zero outcomes.

A bunch of half finished ideas. A shitty singing voice. A Google Drive full of new non-fiction book ideas.


I wasn’t being creatively satisfied as my writing was crap. I also had all these good songs unrecorded that are very important to me, things I want to say, and they were just sitting there unrealized. That makes you unhappy.

So, I finally took a step in my goal planning and have tweaked my process for this year.

Now, I have 4 categories. And I can only pick one yearly outcome for each.

In this post, I’m going to share my personal system and some advice that I’ve picked up from reading a lot on the subject.

Because in 365 days from now, I’m going to achieve everything I list in this post.

I’ve done it before.

And I’m going to do it again, goddamn it.

The question is—you gonna come with me?

The three things you need to remember

  • You’ll achieve more, if you stop trying to do everything.
  • You have to make tradeoffs.
  • Focus on tangible outcomes, not desire.

All will become clear. Let’s set some goals!

Have you ever set a goal you achieved?

I’m not a successful entrepreneur, famous author, or that talented.

But in the past few years, I’ve been checking things off my list.

About five years ago, my big goal was to be published in magazines. Just to be good enough to write in a magazine. It didn’t matter what. A book review, celebrity gossip, I would have written an astrology column if they wanted.

I also wanted to be a published author. A real book in Chapters! Wouldn’t that be cool?

I also wanted to write a blog that people read. I set a goal for 5K monthly pageviews. It seemed like a huge number.

And money in the bank. I’ve always worried about that. So, I wanted to make $100 in passive income online.

And finally, I wanted to get out of career limbo and have a real career.

I’ve been published a few times now and as part of my job, I’ve had stuff I’ve written appear in popular publications. I actually don’t care about this goal anymore, but sometimes you need to achieve something to move on.

Last year, a major publisher offered me a publishing deal for my eBook. My book would be in real stores and they wanted to build me into a career author. I turned them down, mostly because I don’t really want to be a self-help career writer. My eBook was what I had to say on the subject.

This blog had 93,000K monthly pageviews last month. So it’s come a long way from my first 5K month. But this is not an important goal for me anymore.

I make between $500 and $700 per month in passive income. This was a fun goal and I’m keeping it.

I now work at one of the best global companies in my industry. It’s a dream job. My career is one of the most important things to me.

I’m not an expert at goals. But I’ve thought a lot about them and taken a few wrong routes.

Here’s the only thing you need to know.

One goal. One year.

Many years ago, long before the Rolling Stones were the Rolling Stones, Keith Richards had a humble goal. He wanted his band to become the “best rhythm and blues band in London town.” That’s it. He didn’t want to become rich or be the biggest band in the world or get a record deal. Just be the best in his city at a specific genre of music.

He thought he had a shot, too. Keith had been buying all these records from the American South. Down there in the South, he wouldn’t have thought this goal possible. The real rhythm and blues bands were too good and Keith was just an eighteen year old kid. But London–this was feasible. And so he went after it.

The reason why your goals don’t work is that you focus on habits, instead of outcomes. Saving 20% of your income, getting in shape, and working hard to find a better job—these are behaviors, not goals. Behavior is important but easily shifts.

You won’t achieve anything until you have singular focus

Every year, you need one simple, big goal.

Not a stupid goal like “I want to be a writer!” Or: “I want to make a 100K per year!”

But a singular achievable goal that is feasible to achieve in one year.

Focus on outcomes. It’s the only way to keep yourself honest.

Here’s the framework

Is your life in crisis?

If you are broke, desperate for a career, hunting for a life partner, or need to accomplish something that will make you happy and complete, then I recommend only creating one goal this year.

Just remember to focus on outcomes, not behaviors.

If not, you are lucky! You get to create 4 goals, one big goal for the 4 important areas of being a happy human being: Personal, Financial, Spiritual, Career.

Achieve a big outcome in each of those categories every year and you’ll be a happy soul.

As I have no crisis, I get to choose 4 goals. Each of these correspond to a part of my life.

With this system, it’s important to not care about the tactics too much. You figure out those on the journey. But right now, you need to look at the big star over the mountain and say, I don’t care what swamps I need to swim through, I’m getting through and reaching my goal.

For example, I set a goal for saving 10K in one year. That same year, I had an offer to do some freelance work. This meant, goodbye Saturdays. But it offered a clear path to my goal. I reached that goal and it’s my new favorite goal.

If I didn’t have such a measurable goal (for example, save 20% of my income), I might have skipped on the goal.

So, don’t worry if you are missing tactics. I’ve put some of mine down. But they might change as I start moving.

These are my goals for the next 365 days.

CAREER (Because this needs to be tended to grow)

Develop one content strategy that has a big win


> Publish 3 amazing, lead gen pieces
> Deepen my knowledge of content strategy
> Spend 100 hours listening to enterprise customers

PERSONAL (What makes you happy?)

Record 10 of my original songs by Dec 2015


> Spend 1 weekend every month recording at home
> Don’t record new songs; record the ones already complete first
> Don’t get distracted by other pursuits

FINANCIAL (Because poverty is fucking miserable)

Save 10K by Dec 2015


> Finish draft of my new eBook project
> List my eBook on Kindle
> Never touch any passive income or freelance money

SPIRITUAL (To not be a selfish ass)

I’m a godless heathen and so I skip this one but some people like to volunteer and do things like that. I might one day include this when the days of me actually roasting in hell are more imminent.

But I am starting to chip away here and include family and friend goals here:

> Go on a trip with my old, good friends
> Spend more time with my sister

The three things you need to remember

  1. You’ll achieve more, if you stop trying to do everything.
  2. You have to make tradeoffs. Only pick one goal per category. For example, music is my personal goal. I don’t get to have a killer beach body.
  3. Focus on tangible outcomes, not desire. “Get a job as a marketing analyst” is a desire. “Read 55 books on marketing analysis in 365 days” is a tangible and measurable outcome.


If you still haven’t decided a career direction, read my post with 35 awesome jobs for English majors. Then read this really helpful interview. This article on how to write a cover letter is also helpful.

If you are serious about finding a career and want step-by-step instructions, my eBook outlines a 18-week practical roadmap. Also, my email course has a lesson on it. You can sign-up for the email course on the right >>>>.

  1. This is honestly, one of the most beautiful articles I have read in a long time. I love the way you seperate desires from true goals, and I’ll take your strategy to heart the minute I figure out what exactly I want to do with my life. As of right now I know I don’t want to go to college to party away the pain of a major that will get me nowhere though I most certainly love, earn a degree I will never use, and become the walking shame of my father, bless him, who really wants be to become a doctor.

    Once more, I don’t know what I want to do with my life other than the fact that I don’t want to live in a cardboard box, but when I do figure it out I’ll be a girl with a plan thanks to your writings. Thank you so much, and have a fabulous day.

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