What I Learned in Failing to Achieve my Goals in 2018

And the implications for you in 2019 and beyond

Matthew Kent
Dec 20, 2018 · 12 min read
Photo by NordWood Themes on Unsplash

There was a time when I would never set goals. Every time a new year would roll around I would silently laugh at all the people making New Years resolutions that I knew they’d never keep.

Then, something happened.

Or rather, a couple of things happened.

The first was that I realized that I had become complacent and was reacting to what life was giving me instead of creating the life I wanted.

The second was that I started relentlessly consuming personal development content.

This gave me the confidence to try what so many people fail at: setting real goals for myself. I was convinced that I was going to be finishing this year patting myself on the back for crossing the finish line of five challenging goals.

As the title of this post indicates, that’s not what happened.

What follows is a look back on what influenced my thinking of goal setting, how I crafted my goals for 2018, and where I think I went wrong.


Aim High

I first starting thinking about goals when reading Tim Ferriss’s The 4-Hour Workweek and listening to his podcast.

His general advice seems to be to aim high. Really high.

The idea is that we are all conditioned by our culture to fit in, pushed toward mediocrity. In those rare instances when someone steps outside their comfort zone, they usually just take a bay step rather than a huge leap.

This means that in some cases it might even be objectively easier to accomplish big goals than small ones. Tim mentions that if you are raising capital to start a business, investors are used to hearing pitches where people ask for $10,000, but if you ask for a million, you won’t have much competition.

Setting a goal ridiculously high can also break you out of the mental barriers that are holding you back.

One of the questions that Tim likes to ask is some version of “how can I accomplish my 10-year plan in the next sixth months?” Obviously it doesn’t always happen, but it’s an exercise designed to constructively break your own thinking and open you up to new possibilities that you wouldn’t normally consider.

This James Cameron quote that Tim included in his recent book Tribe of Mentors sums up his perspective on goal setting rather nicely:

The Discomfort Zone

The next thing that greatly influenced my thinking was episode 243 of Pat Flynn’s Smart Passive Income podcast.

His guest was the author Michael Hyatt and the topic was, you guessed it, setting goals.

I took a lot of notes on that podcast, but the thing that probably stuck with me most was a story.

Michael bought a dog collar called an “invisible fence” to train his dog to stay in their fenceless yard. The idea was that if the dog tried to go out into the street, the collar would give him a small shock (this sounds kind of mean, but apparently it was a pretty busy and dangerous street, so really he was keeping the dog safe). The crazy thing was, even when they took the collar away and there were no more shocks, the dog still wouldn’t cross the street, even if you tempted him with doggy treats.

Obviously the point of the story is that you and I are like the dog. We’ve been conditioned to settle for 9–5 jobs with 3% raises, failing health, and a cozy but mediocre life in the suburbs. We never step out of rut because of an imagined pain that actually might never come.

In that sense, Tim and Michael seem to be coming from the same place. But unlike Tim, Michael doesn’t think you should just aim as high as possible with your goals.

According to Michael, there are three zones we can operate in:

  • The comfort zone: The land of mediocrity where most of us live by default
  • The discomfort zone: The land of growth where the bold venture intentionally.
  • The delusional zone: The arena of overconfidence where reality can never meet expectation and dreams go to die.

A good goal puts you in the discomfort zone. As I often say:

So the key, according to Michael, is to intentionally step out of your comfort zone but to avoid the delusional zone.

His most memorable lesson was the dog collar story, his most influential lesson was the discomfort zone, but the other one that I wrote down, the one that might have the biggest impact on me going forward, is that actions follow identity.

In other words, as we attempt to transform ourselves, we often fall into what is known as imposter syndrome, the idea that we’re really just a fraud and sooner or later we’ll be exposed.

In other words, if you want to become a writer you will struggle with imposter syndrome because you see yourself as a nobody trying to become a writer.

If you want to lose weight, you see yourself as a fat person trying to be skinny.

Instead, you should start by assuming you’re aspirational identity. You are a writer. You are a fit, trim person.

Once you assume your identity, you ask, what do people like me do?

Well, writers write every day, so get to it.

This is another point that Tim would likely agree on and so would the the next two guys who aren’t huge fans of goal setting.

Growth Without Goals

Along the way I’ve come across two thinkers who aren’t big on setting goals: Scott Adams and James Clear.

Scott Adams is the creator of the popular Dilbert comic strip, and he notes that once you create a goal (especially a big goal), you immediately put yourself in a state of failure. This then advances to a lengthy purgatory of semi-failure as you slowly make progress.

Goals can often create discouragement as you spend most of the time pursuing them far from achieving them.

I’ve definitely felt that.

James Clear is the author of the new book Atomic Habits and he has a similar critique of goals. He also adds other points, such as the fact that goals create a “yo-yo effect” as after you achieve your goal you laps back into the same behaviors from before you set the goal.

So how do you get where you want to go without having a goal as the primary driving force?

These two thinkers have two different terms, but they amount to the same thing. Scott Adams talks about systems and James Clear talks about habits.

The idea here is that getting where you want to go won’t happen in a sudden flash of inspiration, it will be the slow process of following a consistent framework that moves you in the right direction.

Right now this is the thinking that is resonating the most with me, and as we look at my goals from 2018, I think we’ll see how systems thinking was actually responsible for some of my best successes, and could have helped me be more successful in some of my failures.


My 2018 Goals

Here are my goals as written in my bullet journal:

You’ll notice that because I’m kind of a dork, I have categories for my goal and each one has a cheesy name.

Each goal also has action steps that I planned to do to achieve the goal as well as the standards by which success was measures (I failed at every one).

Looking back, I think that creating the action steps was the best thing I did last December. That comes the closest to the systems thinking that I am trying to move towards.

I think the “how success will be measured” portion was the weakest. The main problem was that I often set a standard that included things beyond my control. For example, in “Operation build a following” my goal was 2,000 email subscribers by the end of the year. That’s a result that ultimately isn’t in my control.

Let’s go through my goals and see what I could have done better:

Health: Operation Six Pack by Summer

Action steps: rigidly stick to diet 6 days/wk, daily ab workouts

How success will be measured: Body fat <15% by 6/30/2018 (starting 21.7%)


Ah, the vanity goal. I would really like to pretend I’m above this, but I’m only human after all.

I had lost a bunch of weight in 2017 following the slow-carb diet from Tim Ferriss’s The 4-Hour Body and thought that with a little work, I could have that elusive six-pack.

Notice that this wasn’t a goal for the end of the year, but halfway through the year. That was intentional. It’s not just the fact that “six-pack by summer” is a thing and that’s the time of year when you’re most likely to have your shirt off, it’s that I knew I would probably add back a little softness in my midsection around the holidays (check ✔️).

I think my main problem here is that the result is out of my control. In theory, a combination of healthy eating and ab workouts should eventually result in visible abs, there’s no way to make this happen faster by “trying harder.”

Since I was mostly wrapped up in the result (vanity again), I ended up quitting when I was close to the deadline and seemed to have stalled in my results.

That’s a real shame, because this was a goal that actually had systems to support it (the diet and daily ab exercises).

Relationship: Operation Dating Game Upgrade*

Action Steps: Plan ahead for dates every other week, plus six “extras”

How success will be measured: 30 dates in 2018

*Just to be perfectly clear, I’m married and I’m talking about going on dates with my wife.


I think the error for this one came in the action steps. The way I set it up, I was relying on willpower, which rarely works.

The fact is, there’s one part of planning a date that I find extremely unpleasant and am prone to procrastinating on: securing babysitting.

In order to be successful, I should have set up a system that made this easier for me. One system was suggested to me a couple of weeks ago by a friend: I could have set up a spreadsheet with the dates that I wanted to take my wife out and had the couples that we sometimes swap babysitting with sign up for several nights throughout the year.

Even if we didn’t fill up all the slots initially, most of the work would have been done with one fell swoop.

Personal Discipline: Operation Up and At ‘Em

Action Steps: Set alarm for 5:30 am 6 days/wk

How Success Will be Measured: Waking up early at least 313 days


This is the goal that I did the best with for the longest period of time. For a very long time this year, I was actually ahead of pace. Then the wheels came off.

I got sick in early September and never really got back on track:

For those interested, this simple system is sometimes called the “Red X Method” and sometimes “the Seinfeld Method” after a story where Jerry Seinfeld told an aspiring comedian the key to success was to write a joke a day and to track his compliance with red x’s on a calendar.

I kept this laminated page (which my wife was kind enough to print for me) along with a red sharpie on my night stand. On days where I woke up at 5:30 and got to work, I would check the day off with a red X.

Two things stand out here: my perfect March and July. Both of these produced massive results.

One of my big accomplishments this year was self publishing a book called Personal Finance That Works For You: How to Build Wealth, Design Your Future, and Make Money While You Sleep on Amazon Kindle. I completed the first draft entirely in the month of March, working for an hour and a half or so each morning before work.

In July, I started a series, 30 Lessons About Life You Should Learn Before Turning 30, most of which I published in August.

Thanks to the time spent consistently writing in July, I published more posts in August than I had before or since. This time was critical to me building momentum on Medium.

I did a really bad job getting back on track after I fell off the wagon, but I’m going to revisit this habit in 2019 (along with the red X system).

Career: Operation Build a Following

Action Steps: publish 1/post week and expanding my distribution hoping to acquire new email subscribers

How Success will be Measured: 2,000 email subscribers by 12/31/2018


Again, the problem here is that I can’t control the end goal with the action steps.

You probably noticed what should have been blindingly obvious to me when I wrote these goals: when your plan includes the phrase “hoping to” it’s not a real plan.

For what’s it’s worth, I actually averaged more than a post a week, yet fell woefully short on the final results: as of 12/15/18 I have 265 email subscribers,* and I’m grateful for every one.

*yes, this includes my mom

Education: Operation Learn and Grow

Action Steps: devote 10 minutes daily to online courses

How success will be measured: complete four paid online courses by 12/31/2018


I think it’s important for everyone to take their own continuing education seriously.

I’ve written about my goal to take four paid online courses in 2018 before:

The bottom line is that I wanted to supplement my reading habit and to get some “skin in the game.” When you pay for something, you become determined to “get your money’s worth.”

I’m only going to make it halfway to hitting this goal. At the beginning of 2018 I bought four courses from Udemy for about $12 each. Early on, it looked like I was going to make it through them by June as I was watching the lectures every day.

That all changed when I got to the excellent course How to Become a Bestselling Author on Amazon Kindle by Tom Corson-Knowles, a self-published author who was making six figures a year off his books on Amazon Kindle.

After finishing the course I immediately set out to write by own book, which I published on Amazon in June.

I don’t make a lot of money off of it each month, but I do make money each month, and it sure is nice to make money on something I haven’t worked on since June.

By the time the book was published and I was ready to start back with the online courses, I was too caught up in growing my audience on Medium to devote any time to online courses.

I’m not very upset about this: the primary factor in my continuing education this year is the fact that I’ve read 53 books so far (and I’m not done yet).

If you’re interested in taking the course I took, I can personally attest that it is very helpful in moving you from thinking about publishing a book on Amazon Kindle to actually doing it. The link is below (it’s an affiliate link, so if you do sign up I’ll receive a small commission):

http://thematthewkent.com/kindle-publishing-course

The Plan for 2019

So with all that said, what am I going to do in 2019?

I’m not going to set any goals.

I don’t think goals are useless, but I think they likely work best if you are good at systems thinking and at developing the habits necessary to set you up for success.

In 2019 I’m going to work on my habits and routines. My top priority is getting back into the habit of waking up early to write at least six days a week.

I’ll also be exploring habits that add to my health and promote taking more time to rest (and to rest more effectively).

At some point in the future, I’ll likely be setting yearly goals again.

The most important thing for me to remember right now is this: I’m not a failure because I failed to hit every goal that I set this year. I’m an experimenter who is one step closer to figuring out how to turn my dreams into reality.

If you made it all the way to the end, thank you. This was a long and personal post and I greatly appreciate the generosity you’ve shown with your time and attention.

I hope you crush it in 2019!

Matthew Kent

Written by

Done settling for average. Now I have my sights set on awesome 😎 Get “The Ultimate Daily Checklist,” my free ebook on productivity: http://bit.ly/2pTziwr

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