How to set achievable goals

Systems for refining your goals

The enemy of long-term goals is vague intentions. To turn your life ambitions into reality, you have to make your goals specific–painfully specific. This article is about how to convert vague intentions into a plan you can clearly execute and stick to.

There are five steps to converting a vague intention into a plan that you can actually execute on; those are:

1. Define an outcome

2. Make it measurable

3. Identify actions

4. Set a time frame

5. Plan for obstacles

You might read that list and think you don't need to go to this much effort to plan your goals. If that is the case, I'd encourage you to reflect on your track record. How much progress have you made on your long-term goals? Have you been able to consistently stick to a goal for months or years, long enough to make meaningful progress you are proud of? If you have, good for you. This article might not be for you. If you haven't, take that as evidence that you should try a different approach. It's evidence that you might need to take more extreme care in designing systems to define and follow through on your goals.

If you’ve followed the advice from the first two articles in this series, you will have generated a set of broad life ambitions or goals, roughly mapped out a few ideas of what you would need to achieve them, and narrowed it down to a smaller set to focus on. When done right, that will create higher levels of motivation and commitment than might otherwise be the case. This article will help you convert that initial excitement into a plan you can clearly execute and stick to. 

Define an outcome

Take one of your broad ambitions and ask yourself what specifically would be different if you were to realize this ambition. This is not a list of things you need to do but rather the outcome of those actions.

Here are a few examples to give you an idea:

• Improving my health ⇒ lowering body fat

• Being a better father ⇒ having deeper and more meaningful conversations with my kids

• Achieving greater financial security ⇒ saving $100,000

• Learning a new language ⇒ holding a 5-minute conversation in that language

• Taking up a new hobby ⇒ completing a course or workshop related to the hobby

Make it measurable

After you've defined a specific outcome, it helps to create a way of measuring progress toward that outcome. There are two important benefits to having a specific, quantifiable measure of progress. Firstly, your motivation increases when you can see incremental progress. Secondly, when the measure is not changing, it gives you early feedback to try something else.

Sometimes, the measure is obvious; other times, you have to be more creative. For example, one of my goals is to be able to do a muscle-up (a particular gymnastics maneuver). The problem is the number of muscle-ups I can do doesn't give me any meaningful feedback or sense of progress. If I were to track my progress, it would be:

• Week one = 0

• Week two = 0

• Week three = 0

However, with some thought, I realized that the percentage of my body weight that I can pull up is a close proxy for my ability to do a muscle-up. I later learned that pulling 54% of their body weight is sufficient strength for most people to do one muscle-up (demo video). My maximum pull-up is very easy to measure and gives me meaningful feedback. Tracking my progress now looks like this:

• Week one = 35%

• Week two = 38%

• Week three = 43% 

Here are a few examples of how you could break down tricky to quantify long-term goals:

• Writing a book ⇒ number of chapters completed

• Learning to cook ⇒ number of recipes you can cook without guidance

• Growing personal confidence ⇒ keeping a log of situations where you felt out of your comfort zone but proceeded anyway

• Becoming more active ⇒ number of weekly steps

Identify actions

Once you have clearly defined your desired outcome and how you'll track your progress, the next step is to identify the specific tasks needed to make it happen. Breaking down big goals into smaller, manageable actions reduces the risk you’ll feel overwhelmed by the enormity of the goal. By focusing on smaller individual tasks, you are much more likely to actually start working towards achieving your ambitions

For example, if your goal is to write a book, the specific actions could include:

• Scheduling regular writing time

• Researching topics for each chapter

• Setting up any necessary interviews

Even if you don't know all the steps upfront, you should be able to define the first few steps to get started. If you have no idea where to start, you can always begin by researching or talking to people who have achieved the goal you have in mind.

Here is a real example from one of my 2024 goals 👇

Set a time frame

A clear finish line makes maintaining focus easier. Without a timeframe, focus and excitement tend to fade until you eventually give up. I recommend committing to a shorter timeframe than seems reasonable, like three months. You can always recommit later. Over time, you'll better understand what you're capable of and can establish systems allowing you to extend your goals to longer periods. 

Regardless of the overall timeframe, it also helps to set interim milestones, such as monthly or weekly sub-goals. This prevents you from deferring effort to your future self and ensures you're making consistent, incremental progress.

You can see the impact of deadlines on my productivity in the chart below. One of my 2024 goals is to publish 52 pieces of content. Knowing that it is unlikely to ever feel urgent, I set myself a publication goal every month. The chart below shows my rush to meet that interim goal every month.

Even though I am rushing to meet the deadline each month, when zoomed out, I am making fairly linear, consistent progress toward my annual goal. Without those mini-goals, that would not be happening.

Plan for obstacles

If you are trying to accomplish an ambitious goal, you will hit obstacles along the way. In some instances, those obstacles are totally unavoidable. However, in most cases, they can be avoided.

When initially planning our path toward realizing a goal, we imagine that everything will remain the same as in that instance. So if it's a warm, sunny day when you have plenty of time and aren't feeling overwhelmed, you imagine that when you wake up tomorrow, the next day, and in 5 weeks, you'll feel exactly the same. We feel certain we can achieve our goal because we fail to recognize that things will change. Critically, our internal state will change; we will inevitably become less excited by our goal, feel stressed about the day's pressures, and eventually conclude that we're better off not working on the goal.

This is a famous psychological phenomenon known as the planning fallacy. A mountain of research shows that when planning ahead, people underestimate the time, costs, and risks involved. Even though we've failed to stick to our goal for the last ten years, we somehow delude ourselves that this time will be different.

One way to minimize the impact of the planning fallacy is to honestly think about your biggest internal obstacles. You have to carefully consider what will get in your way and stop you from achieving your goal. Try to imagine the obstacle as clearly as you can. If you've worked on a similar goal in the past, reflect on why you couldn't make progress last time.

In my experience, these are some of my most common internal obstacles:

• Fading motivation: My motivation tends to fade over time, especially when my progress isn’t immediately visible.

• External distractions: Life events and changes in my personal situations divert attention away from long-term goals, such as a stressful time at work, travel, or illness.

• Poor time management: Sometimes, I don't effectively plan and divide my time between various commitments, which can lead to me rushing and not making meaningful progress on goals.

• Procrastination: I often delay tasks because I feel overwhelmed or uncertain about how to start.

Once you have identified your obstacles, you are in a more powerful position because you can start to find solutions to reduce their impact. You can ask yourself, what can I do today to reduce the impact of these obstacles? Write that down and build it into your plan.

One method I have found very impactful is mid-point check-ins. If I am working toward a long-term goal, I like to schedule checkpoints along the way where I can reflect on how I am doing and adjust my plans.

For example, when thinking about obstacles to maintaining my healthy habits, I noticed one thing: my habits start fading when I travel. Knowing that was a big risk for me, I made a plan before my next work trip. I scheduled the email below to send to my wife halfway through the trip. That way, when she received the email, we could discuss how I could adjust my habits based on my new environment.

Updating your plans to account for obstacles increases your resilience to setbacks, making you more likely to achieve your ambitions. With a motivating and robust plan, you're ready to start working. In the next article, I'll share how you can stay consistent over long periods.