A small plant sprouting in dirt.

How To Set Goals (When You’ve Come Up Short In The Past)

Lessons from a serial failure (and goal-achiever for nearly a decade).

I’ve been in your position. Stuck. Annoyed. Dreaming of a better life but coming up short again and again. Especially when it comes to your goals – particularly with the process of how to set goals.

Because people make it seem easy.

  • To start that business
  • To buy that house
  • Or to take that trip to Iceland, Thailand, or any other place with land in the name (Finland)

But it’s not.

Which you already know. You know achievement doesn’t come quickly. You’ve heard the examples of how overnight successes only appear that way in the media. How it really takes years of hard work to reach some miraculous destination.

You know that. You know you should be patient. And yet, you’re not.

You’re frustrated. Frustrated that you can’t seem to make it work. You’ve dreamt of a better life, you’ve planned for it, but when it comes to your goals you keep coming up short.

You’re not alone.



I’ve started a lot of businesses. And all of them have failed. All of them but QuickBooost (what you’re reading right now). QuickBooost is the culmination of seven years of failure and lessons learned.

Of really great experiences, and really great disappointments.

Of hard times.

I started my first business while in college. It was an app that helped fellow students better connect to their local clubs and businesses. I hired a freelance development team to build it and ran everything as lean as possible. It folded a couple years later when I couldn’t get it to grow.

Like a dud pumpkin seed, it never sprouted. It died.

From there I joined a tech startup.

We were a small team, building an app to help young adults make plans and connect with their friends. A year later, we couldn’t get it to grow and that company too closed. It was at this point that I started to panic.

I was zero for two and didn’t like how I was trending.


It didn’t matter

After leaving that startup, I held a couple different jobs while pursuing my entrepreneurial ventures on the side.

I tried freelance writing. That lasted about a week at which point I realized I couldn’t do it sustainably. I created an eCommerce business selling safety razors. That died two months later when I couldn’t get anyone to make a purchase.

I started a watch brand.

I connected with manufacturers in China, took product photos, built the website, and started marketing it. Further, I found a local nonprofit that I would donate a portion of my earnings to. It didn’t matter. My company died within six months when I, again, couldn’t make a sale.

Failure after failure after failure after failure.



A cemetery facing the ocean.



Technically, I failed. And yet, each of those experiences helped me learn and grow.

When I first started building businesses, I had zero knowledge of what to do. I was starting from scratch. Those early projects, while not ending the way I had hoped, served as a foundation for what I know today. And for that, I’m grateful.

But you already knew I was going to say that. It’s the standard thing to say. It doesn’t make it any less true though.

I started QuickBooost (again, what you’re reading right now).

I took the lessons that I learned from my past experiences and applied them to this new exciting venture. With hope, I built the website, wrote content, and started trying to make it work. And hey! The pumpkin seed started to sprout!

Not a ton, just a little.

But more than any other seed had ever grown before. *Not sure why I went with the pumpkin seed analogy, but I’m not turning back now.

QuickBooost had promise. It still does.

Looking back, I can see why each of my previous businesses failed. But this isn’t a post on venture lessons learned. It’s one on goal setting. So I will push the dialogue in that direction.


Not a fan

There was a period of time when I wasn’t a fan of my body. I felt… large. Bulky. I’d feel self-conscious when the wind would push my shirt against my stomach as I walked.

So I set out to lose some weight.

And you can probably guess the rest of the story from there.

I tried the various fads (ie. juice cleanses), took the recommended supplements and vitamins, and started going “hard” at the gym. But oh uh, I began gaining weight. Pound after pound, the scale would increase. I was going in the wrong direction. And after several years of this, I hit my peak poundage.

Things were not looking good.



Three years

Then one day, I changed my eating habits. I don’t remember the exact scenario because it’s been many years since then, but the gist is that I started eating better. Healthier. Fewer calories.

I started focusing on the foods I took in as opposed to the energy I expelled (ie. exercise).

I began to take calorie tracking more seriously and started holding myself accountable to it. Sure, I still exercised but I began doing more cardio as opposed to weightlifting – which I enjoyed more. And over several years, I gradually lost the weight.

Not all at once.

Not quickly.

Probably one pound a month, every month, for roughly three years.

It took a long time, and a lot of lessons had to be learned the hard way, but I eventually achieved my goal. I reached my ideal weight and have maintained it ever since thanks to the lifestyle I designed for myself.

Blow as much as you want, wind. I am self-conscious no more. *Just take it easy on me after I eat pizza. I’m not Superman. 


A Lego Superman standing on a tree stump at dusk.


Checkpoints on the road

Failure is something you experience on the road to growth. It’s inevitable. And when you run into it, it’s your job to learn from it. Even when it’s hard.

To apply those lessons to your goals moving forward.

Because you need goals. Goals are the things in life that guide you forward. That push you towards your vision of success. You can’t give up on them! If you give up on your goals, then you give up on your dreams.

And no one wants that.

So instead, let your failures inspire you. Let them motivate you and serve as checkpoints on the road to greatness. You can’t succeed without failure. So see each moment of “non-success” as an indicator of progress, not defeat.



That said, I have found that there are common pitfalls that many people run into when working towards their goals. And how, by avoiding these obstacles, you can better set yourself up for attaining what you’re after.

But that’s a whole other topic of conversation. That’s the second half of the equation. The achieving side of things. You can read about that here.

At the onset though, you need a logistical structure for your goals.

A system for mapping them out so that you are organized and can easily achieve them. With that in mind, when it comes to how to set goals, apply the following steps and set yourself up for success.


How to set goals: Write them down

Most people have no trouble figuring out what kind of goals to set for themselves. Just take a few minutes to daydream about a better life and you’ll be filled with all sorts of dreams and notions.

That’s not the problem.

Thinking up the goal is the easy part. It’s the fun part.

The planning and logistics that come after are often the parts that get neglected by many. Especially if things feel uncertain or you aren’t confident in your abilities. But to be successful with your goals, you need to write them down.

It doesn’t have to be anything fancy. You don’t need any special formatting. When it comes to how to set goals at work, or at home, in relationships, or with your fitness, just write down:

  • What you want to achieve (aka your goal)
  • Why you want to achieve it (aka your reasoning)
  • When you want to achieve it by (aka your deadline)
  • And what actions you will take each day, week, and month to achieve it (aka your plan)

Write it somewhere that you will see it. Somewhere that you can come back to each week and update accordingly.

Write down your goals and the logistics behind them so that you are prepared, organized, and focused on what you need to do. Don’t let them float around in your mind; to be lost in space along with your car keys and middle school retainer. Take note of them so that they become real. 

So that you remember and work towards them.

Keep in mind, I do recommend some goals over others. For more on that, I suggest reading this.


How to set goals: Check in

Something else that you need to do when it comes to how to set goals is check in with yourself. At least once a week. Depending on the goal, maybe once a day.

Look at where you wrote your goals down. Consider if you are:

  • Taking the actions you need to each day/week
  • Progressing the way you hoped you would
  • Working in a manner that is sustainable

If you are taking the necessary actions and are making progress, great! Keep going. If you aren’t, why? Are you not making the time? Were you too ambitious in your initial plans?

See your first few weeks as a time for learning and adjustment. Don’t give up when you aren’t seeing the results you want or aren’t putting in enough effort. Be kind to yourself and adjust things until it feels a little more manageable.

Along those same lines, when you do your weekly check in, use that time to plan out when you will work towards your goals in the coming week.


When it comes to how to set goals, give yourself freedom to adjust things as you learn. Just like a thermostat.


How to set goals: Plan for them

Something I’ve done for what feels like forever, and what I also found noted in books like The 12 Week Year and Free To Focus (both here), is planning for your goals.

When it comes to how to set goals in life as a whole, it’s great to write them down. It’s great to check in on your progress. But just as important is the need to make time for them. To look at your calendar, schedule, plans, and appointments and intentionally make time in your life for the pursuit of your goals.

Without this step, I can guarantee that you will either:

  • Not make any progress towards your goals
  • Or feel so scattered each day that you won’t make the progress that you could

Even if you aren’t the planning type, when it comes to your goals you will benefit from doing this.

That point is infinitely more important if you have multiple goals that you are working towards at the same time. Take some of my current goals for instance. At the moment I am:

  • Reading/Listening to at least two books a month
  • Working to improve my home in at least one way each month
  • Practicing speed reading twice a month
  • Working to publish six posts by the end of the month
  • Plus many more goals not listed here

If I didn’t take the time to plan, my days would be chaotic. I wouldn’t know what to do or when to do it and I would severely weaken my effectiveness each day. Planning is necessary to ensure that you make time for what matters.


How to set goals moving forward

Having an idea for a goal that you want to achieve is easy. Not enough people though take the time to work out the logistics to wisely set themselves up for success.

Don’t be the majority. Be better.

When it comes to how to set goals and achieve them, make the effort to write them down. Spend the time each week to check in on your progress. Push aside room in your busy schedule and make time for your goals.

Don’t see your shortcomings as failures. See them as checkpoints on the road to greatness. As lessons learned. As a honing of your direction. Let them serve as your guide to doing things better.

Plant your pumpkin seeds and watch them grow into something amazing.

Want to hear more from me?