How a former athlete uses the same methodology as Google and Spotify to achieve his goals and how you can do it too.

I have failed at achieving goals. Haven’t we all?

Less than 10% of people stick with their New Years’ resolutions. Even though these people may not be athletes, I can testify as a former goal-driven athlete that I know there are loads of us sportspeople who don’t achieve the goals we’ve set for ourselves or our teams.

While setting goals might be easy, we know achieving them is not. Well, for the past three years, I have been using OKRs to set – and achieve my goals. Want to learn how?


When my life after football started, I had a bunch of cool ideas to pursue. The one that I ended up giving a shot turned into a complete failure. Looking back, it’s easy to point towards the mistakes that led to my company-you’ve-never-heard-off.

I wanted to build an app – well, who didn’t at that time? – but I had zero experience going through the process. Even though a lack of experience does not equate to definitive failure, it definitely justifies an emphasis on being well-prepared and organized. My reality; I didn’t know how to be organized, run an operation, and manage the process of building a business. Today, I find it easy to see why the business failed, but I had a hard time figuring that out while the failure happened before my eyes.

In the years after this attempt at a startup, I had the pleasure of working with small and large organisations, helping them to find and validate business models.

During these projects, I learned the benefits of implementing structure but more importantly, I have learned how to organize myself and my work to position myself and the team for success.

In just a couple of years, I went from failing at building my own startup to finding and validating business models for corporates, investing in startups, and building my own community of investing athletes.

You’re probably wondering how I managed this turnaround? Simple, I learned how to effectively use OKRs.

Therefore, I’m writing this blog to introduce you to the OKR methodology, which is designed to help athletes set – and achieve – inspiring goals. To be fair, the OKR methodology is not really designed specifically for athletes, but given the way it’s structured, it fits perfectly with how athletes pursue objectives. And yes, it also works for non-athletes :).

The OKR methodology is used by high-growth tech companies like Google and Spotify, but also brick-and-mortar conglomerates like Walmart. But, before we dive in, allow me to introduce myself and why it matters to me that you learn to set and achieve goals, outside of sports.

About me

My name is Jason Esseboom and I’ve founded Joyned Capital to transform athletes into smart investors.

I’m writing a weekly blog to make education accessible to every athlete that wants to learn about investments. Even if you haven’t subscribed to my e-course on investing yet, I still want you to learn.

In order to achieve the goal of becoming a smart investor, you’ll need to be able to plan towards it. That plan starts with setting clear markers to measure your progress towards success. So, let’s look at how we can make that happen.

What are OKRs?

OKR is a goal-setting methodology, and as mentioned widely adopted by tech companies like Google and Spotify. However, it all started with Andy Grove, the first CEO of Intel (yes, check out this link if you’re a background geek, like me).

When using OKRs, you’re setting Objectives that inspire you beyond your wildest dreams. These Objectives are qualitative (simply put, not measurable) and may contain words like “best”, “most powerful”, or “happiest”.

But how do you know you’re on the right track to achieving your Objectives?

This is where Key Results come into play. Key Results are quantitative, meaning they are designed to be measured and track the results of your efforts.

Keep in mind; while setting goals might be easy, achieving them is not. Less than 10% of people stick with their New Years’ resolutions and one of the main reasons is that people set vague and uninspiring goals.

I know these people are probably not elite athletes with the persistence and determination you have, but we have all failed at some goals throughout the years. Well, I’ve found a fix, because for the past three years, I have been using OKRs to set – and achieve – my goals.

So, it’s clear by now that in order to achieve your Objectives, you need to put in the work. But that work should lead to measurable results; you want proof of your improvement, so to speak. here’s how you do it.

Applying OKRs to sport

Imagine you want to become the best player in your football league, which is a pretty inspiring goal. To break your goal down into measurable components, you should look at what makes you the best player and set the right Key Results.

Things that come to mind are goals, assists, and % duels won. Sure, there’s more to being the best player, but if you’re consistently scoring the most goals, giving the most assists, and winning the most duels, chances are you’re going to lead the charts.

After thinking long and hard, your Key Results could be:

  1. scoring 20% more goals than the number 2

  2. 10% more assists than the number 2

  3. winning 40% more duels than the number 2

If you do this exercise properly, your Key Results measure an outcome instead of progress. Remember, you’re looking to become number one (an outcome), which means you always need to be better than the rest. Therefore you should pick a number that is XX% higher than the next player on the charts.

Great, so how do you apply it at Joyned Capital?

I’ve set three Objectives for Joyned Capital, each supported with two or more Key Results to measure our performance. Here’s how I applied the OKR system this week:

Week: October 4-8, 2021

Objective: Joyned Capital has the best educational investment content for athletes

Key Result: 1000 hours writing of investment content within one year.

Tactic (to achieve Key Result): Write a weekly blog

Experiment (to achieve Tactic): Start each day with measurable goals for writing content and write review notes about performance at the end of each day

Result: I didn’t write down the goals 2/5 days, wrote reviews 4/5 days.

Learning: When writing this blog I didn’t need the notes because the week is still fresh in my mind. I assumed that writing down the goals would help me to write a good blog about how my week has been. The days I did write down goals I clearly was more focussed – checking off >80% of goals – compared to the days I did not write down goals – varying from hitting 40-80% of my goals.

Next week: For next week, I’m planning to timebox my work, regardless of whether it’s a call, writing, or reading. I want to get more insight into how I spend my time and where I can improve.

How can I learn to work with OKRs?

Great sources are blogs like this or you can try this one. Obviously, I’m happy to share my experience to help you set your goals. Investments might be a new arena to you and it’s hard to combine this with an existing career as an athlete.

Learning to work with OKRs can help you to reach the same – or even higher –  level of success you’re used to as a pro athlete.

What if I want to learn more about investing?

Feel free to reach out to me directly, here’s my LinkedIn & Twitter, or schedule a call.

See you!

Jason