How To Set Goals and Achieve Them

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It happens all the freaking time.

The calendar rolls from one year to the next or something else happens, driving us to reflect, get ambitious about our lives, and charge towards better.

We want better for ourselves. We want better for our loved ones. We want to leave our mark on the world.

We want more freedom, more time, more money, more love, more fun.

We want more!

We say “enough is enough” and dive head first into the hard work of changing our lives.

We wake up early and go to the gym. We trade chocolate for kale. We stop buying stuff we don’t need and can’t really afford so we can pay off our debts.

But then a few weeks go by…

We sprain an ankle and skip a workout. We have a rough day at the office and numb the pain with something sugary.

And of course, there’ll be a sale too good to pass up (We’d practically be losing money by not buying, right?).

And just like that, life reverts to how it was.

Or maybe we don’t even get that far. Maybe we try to come up with the perfect plan to perfect our lives, but instead we suck all the pleasure out of it, get scared, and do nothing.

Sound familiar?

I’m willing to bet it’s not just me.

Never content to just take life as it comes, I’ve tried to make the most of what God’s given me to work with. But it hasn’t always gone well.

I’ve had plenty of great intentions flame out over the years. Plenty of incomplete projects. Plenty of dusty running shoes and other sporting goods. (Not many tropical SCUBA spots in New England…) And far too many half-read and unread books.

But I’ve also learned a lot about setting goals and breaking them down into actionable bits. And through it all I’ve developed a “process” for changing and improving my life.

It’s how I lost 20 pounds of fat and got myself off prescription painkillers after becoming permanently disabled.

It’s at the core of how my wife and I paid off all our debt in just 7 months and emergency-proofed our lives.

Now, I’d like to distill and share what I’ve learned with you.

I’ve tried to make this process as easy as possible for myself, and I want it to be easy for you too. So, I’ve put together a tool to guide you.

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Sure you could do all this in a journal as I’ve done in the past, on the back of a napkin, or something else. But why go through all that when I’ve put this tool together for you? Make life simple for yourself.

(Just in case you think I sound a bit full of myself or high and mighty: I’m not saying this is the be-all, end-all, only thing you’ll ever need to set goals, learn to take action, and improve your life. I am not a guru. I am not perfect. I have not totally hacked my own life.

But, I am saying this process works for me, it’s worked for others, and I bet it could help you, too. That being said, I’m offering a 100% money-back guarantee.

-But James, I didn’t pay anything for this…


Healthy, Wealthy, and Wise

At least once per year, typically in January because I’m basic like that, I’ll set some time aside to set goals for myself. I’ll think about the things I wish were true in my life. All the things I could do, should do, and need to do in the year ahead.

I’ve started using the old Benjamin Franklin quote “Early to bed, early to rise makes a man healthy, wealthy, and wise” to frame my thinking.

(My wife, Andrea, and I also do this as a couple at the end of each May. But instead of the Franklin quote above, we use each line of our wedding vows to frame our thinking.)

I want to be healthy. I want to be wealthy. And hopefully, I’ll grow wise. So I’ve broken down what each of those look like for me. Feel free to add/subtract as you see fit.

Healthy: Refers to physical, emotional, spiritual, and relational well-being.

Wealthy: Refers to the ways I handle my resources, specifically time and money.  

Wise: Refers to my growth as a person; how I challenge myself, face fears, learn new things, and serve those around me.

Then, I’ll come up with some wishes, or ambitions, for each category.

For example, for “Healthy” I might say:

I want to be physically capable to go do stuff. I want my body to be an asset in my life, instead of a limitation. I want to be emotionally healthy. I want to be happy and resilient. I want to choose how I feel, rather than allow my circumstances to dictate my emotions. I want to explore and develop my faith in God. I want to be a better family member and friend. I want to deepen my existing relationships and make new ones. I want to have fun and do some things just because I want to and life’s too short to be bored.

More specifically, one “Healthy” ambition I came up with this year is to “Do cool stuff with other people.”

This is where I find most people stop. They come up with how they want their lives to look and just
kinda sorta expect it to happen. As though the universe owes them something.

Instead, this is where we’re going to start.

Toyota and the Five Whys

Once I’m done coming up with “ambitions,” I’ll write one at the top of a piece of paper (or in the top of the tool I put together for this process) and ask “Why?”

Why do I care about this ambition? Why does it matter? Why is it important? Why do I want it?


Then I’ll write or type my answer and ask “why” again.

I’ll write out that answer and ask “why” yet again. And I’ll typically do this five times or until I can’t answer “why” anymore. And yes, this can be uncomfortable. But it is critical.


This is something I’ve picked up from Toyota, the largest car maker in the world. Whenever they find a problem, Toyota encourages their engineers to ask “why” five times in order to understand the root cause of the issue. If they don’t, they might fix the wrong thing and simply delay the inevitable problem from resurfacing down the line.

I’m trying to do the same thing. I want to understand the root of my ambitions for two important reasons.

First, I want to make sure I’m working on the right thing. Asking “why” as many times as I do might reveal something I hadn’t thought of and lead to a totally different ambition. My original ambition might just be hiding something I might not realize or I’m afraid to admit I need to work on.

Personal example. One time I was working through my “healthy” ambition to work out more. (I’m so original, aren’t I?) Well, when I asked myself “why” I wanted to work out more, I answered “To look good so my wife will find me attractive.” Yes, that’s a vain answer. And yes I know my wife already loves me finds me attractive.

But when I asked “why” again I answered, “I want break the cycle and legacy of divorce in my family.”


This sent my thinking in a totally different direction. I took some time to focus on other ways I could strengthen my marriage “to break the cycle and legacy of divorce,” aside from working out more.

Second, and this is more often the case, by answering “why” five times I’ll have a solid understanding why an ambition is important to me. That means I’ll be much more motivated to stick with it when things get tough and I’m tempted to quit.

Back to my personal example, answering “why” as many times as I did allowed me to tie working out more to being attractive to my wife. That then tied into breaking the cycle of divorce in my family.

I’d say this is the most important step in the whole process and it’s something I’ve devoted an entire article to before.

Please don’t skip it or rush through it.

The “How About” Game

Once you’ve got your ambitions and why they matter sorted out, it’s time to play the “How About” game.

Here’s how it works.

Take an ambition you’ve answered “why” five times for, then say to yourself “How about I (fill in the blank).

This is where you get to think of all the different things you could do in pursuit of your ambition.


Here are a few examples I came up with for my Healthy ambition earlier to “Do cool stuff with other people:”

-Book a paragliding or hang gliding lesson and invite other people I think would be interested.

-Dust off my SCUBA gear and go diving with a friend who’s interested in getting SCUBA certified.

-Volunteer helping a cause I care about and invite friends who also care about the same cause.

Anything goes. In fact, the stranger the better.

After a while you’ll probably start to run out of ideas. When this happens, ask yourself “What’s the craziest thing I could do?” Don’t skip this.

Often times we’re biased against the very things we should do. We know what we should do, and yet we don’t do it.

We’re afraid. The cost is too high. It’s too much change to take on. So we’ll rule it out.

Don’t. At least not yet.

What we’re going to do

Once we’re done with the “How About” game, we’re going to filter everything you came up with and pick one to do. Just one, but it’ll be the right one.

We’re looking for an “inciting incident.”

In story telling, the “inciting incident” is the thing that motivates the main character to take action. It is the thing all other action hinges on.

In Braveheart, William Wallace finally goes to war against the English when an English Lord murders Mrs. Wallace. In Star Wars, Luke Skywalker runs off with Obi Wan to learn about The Force and fight the evil Empire only after the Empire murders his aunt and uncle.

Now, we’re not going to count on an evil government murdering our families to motivate us to get off the couch. Instead, we’re going to scan everything we came up with playing the “How About” game for something that would work as an inciting incident. (Hopefully, one of the things you came up with isn’t “Murder entire family.”)

Here are some tips for finding your “inciting incident.”

First, focus on actions you can take. We can’t really guarantee the results of action, so don’t get hung up on that. But we can guarantee whether or not we take action. Focus on the inputs, not the outcomes. Pick something you can easily do right now.

Second, look for “lead-dominoes”, things that’ll force other action. This can help if you’re feeling overwhelmed by a goal or ambition. Just focus on starting. Focus on setting things in motion and you’ll be surprised how the the rest will come together.

Third, few things focus the mind as well as a deadline. So set a date in the not to distant future and tip over your “lead domino” by then.  


For example, a couple years ago one of my Healthy ambitions was to run more. I hadn’t run in years and was wildly out of shape. So did I go out and buy bright yellow running shoes? Did I roll out of bed at 430am to run five miles before breakfast? Did I wait for an evil government to try to kill me?

Nope, I just set things in motion.

I paid money and signed up for a 5K race a friend of mine was hosting. And guess what? Little by little, I started running. Having a deadline, knowing I wouldn’t be running alone, and my fear of embarrassing myself in front of those other people motivated me to run.

Maybe you want to travel more this year, but can’t decide when or where. Don’t wait for the perfect time or opportunity (there’s no such thing), just book yourself a hotel in a city you’ve always been curious about by NEXT WEEK. Set your trip in motion and you’ll figure out the visas, flights, time, etc later. (Besides, you can always cancel and get your money back if the trip doesn’t work out for some reason outside your control.)

Or maybe you’d love to get control of your finances and finally break FREE from your debt. Set things in motion TODAY by checking my guide on the best way to pay off your debts and fill out the debt pay-off tool I built for you. In less time than it takes to watch an episode of Bojack Horseman or a couple cat videos, you’ll be able to get a grip on your monthly finances, know exactly what to do to get rid of your debts, and how long it’ll take. Even if you’ve never done a “budget” ever before. 

The important thing is to start. Take a bold, first step. Others will follow. Before you know it, you’ll be on your way to a better life.

If you decided to use the tool I built for you, “submit another response” and repeat the process for every “ambition” you have.


Then, when you’re done you can export EVERYTHING you’ve come up with to a spreadsheet, print it out, put it somewhere conspicuous, carry it with you, etc.

This will help keep you focussed and charging towards a better life.

What are your favorite tips/tricks to setting goals and actually achieving them?

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