How to Make a Smart Decision You Won’t Regret

One simple practice changed my life forever.

Todd Lincoln, MBA
Oct 12, 2020 · 6 min read
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Photo by Alexander Schimmeck on Unsplash

early 10 years ago, I started a simple practice that forever changed how I make big decisions. My life was at a major crossroads, so I wrote an in-depth journal entry about my situation. Without realizing it, I had created a decision journal.

A decision journal is a journal entry where you write about your current situation, examine your options from all sides, spell out which path you’re choosing, and explain why.

Think of it as you interviewing yourself about a big decision, right as you’re about to make that big decision.

It only takes a few hours per decision, and most people don’t average more than one big decision per year. As far as habits go, it’s hard to imagine a practice that delivers more bang for your buck.

It sounds simple, but it’s actually incredibly powerful.

I started using a decision journal 10 years ago because two big decisions in my life hit at the same time:

  • Should I break up with my girlfriend of two years? My breakup decision journal was short, less than half a page of raw, unfiltered emotions driving my desire to move on.
  • Should I shut down my struggling startup? My startup decision journal was much more thorough. It spanned eight pages and included many personal, professional, and health considerations, as well as some light financial analysis and forecasting.

Although very different, both of my original decision journals had an enormous impact on my life for many years to come.

The Benefits of a Decision Journal

Having relied on a decision journal for those first two big decisions, and many more since, I’ve found it helps me improve in three major ways:

Consider the situation from all sides

The act of documenting the thinking behind your big decision causes you to consider the situation from all sides. This leads to better decisions.

Especially when deciding if I should shut down my startup, I found myself almost scenario planning by writing out, “what if I did this?” or “what if I did that?” and then forecasting how each of those paths would play out.

The more angles you consider, the more likely you’ll make a smart choice with a good outcome.

Remind yourself why you made the decision that you did

Regardless of the outcome, I have a tendency to second guess myself after I make a decision. I often look back and wonder if I made a mistake.

For example, I looked back on the decision journal for my breakup during many dark and lonely nights when I was thinking, “I never should’ve left her, that was a huge mistake.” Reading that journal reminded me just how unhappy and unsettled I really felt, and renewed my confidence in my decision-making skills and new life direction. That was huge for me.

Over time, the details of life’s big moments tend to fade and there are a range of psychological biases that creep in and obscure how we truly felt at the time. A decision journal preserves both your situation and your thought process so that you can objectively remember how things really were.

Improve your decision-making skills over time

After some time has passed, you can look at how things played out and compare it to what you expected when you wrote your decision journal.

When I decided to shut down my startup, one of the biggest deciding factors was that I believed that from now on I wanted a healthy, balanced lifestyle more than I wanted a big, successful startup. That forecast turned out to be spot on. I look back now and see that introspective thinking was hugely valuable in making a decision that turned out to be right. Now I always try to pit competing priorities against each other to see which I value more.

On the other hand, when I decided to break up with my girlfriend, one of the reasons was that she didn’t appreciate the art of TV and film like I did. As I’ve grown and matured, I now see that was a shallow reason to end the relationship (it wasn’t the only reason). Now when I make decisions, I’m careful to scrutinize such surface-level reasoning.

A decision journal allows you to look back and grade your decision-making process against the reality of how things played out. Over time, you’ll improve your thinking process and make better decisions.

How to Use a Decision Journal

There’s really no right or wrong way to write a decision journal. Most importantly, I’d do it in a way that will keep your interest and lead to a recurring habit.

I don’t do a journal for every little decision. Instead, I’ve found it more powerful to capture just the big moments in life.

Here are a few strategies you might consider for your decision journal:

Capture all the angles you’re considering.

  • This could be pros and cons, scenario planning, or just your conflicted feelings. Be thorough here — the whole point is to make a good decision, which requires exploring the issue from all sides.

Document your main assumptions.

  • Capturing the “facts” driving your decision will illuminate which beliefs are underpinning your decision-making process. Also, it’s fascinating to look back and see which assumptions were right and wrong.

Write how you’re feeling at the time.

  • This will remind you of your mental and emotional mindset during the decision, which helps you both remember what it felt like and analyze how your emotions played into your decision.

Consider the possible outcomes.

  • Explore how you expect things to play out for various different decision paths. This is one of my favorite parts, as it’s fascinating to compare my forecast to what actually happens.

Reread before finalizing your decision.

  • Don’t worry about polishing your journal from a proofreading perspective (it’s likely no one will ever see it). Instead, make sure the journal entry accurately and completely captures the situation and your decision. Here’s my usual approach: Read. Let simmer. Revise. Repeat 3+ times.

Review soon after deciding.

  • I find it valuable to review my journal entry soon after putting my decision into action in my life. This helps me stress test my assumptions and logic, and see if things are playing out as I expected before I’m too far down my decision path. If I was majorly wrong about something, it may not be too late to change course.

Review long after the dust has settled.

  • Long after I’ve made my decision and the situation has played out, I like to go back and grade my decision-making skills. This helps me make better life decisions going forward.

Most importantly, find an approach that works for you. Don’t worry about the format — it can be a stream of consciousness, a self-interview, a thoughtful collection of considerations, or a well-organized and analytical report (for example, see this template from Farnham Street).

As long as you capture your situation, logic, feelings, and decision, you’ve hit the important stuff.

Most of the value of the decision journal is in the process, not the final product.

Keeping a decision journal around big life moments has become a mandatory practice for me. It helps me make a fully informed decision, prevents me from second-guessing my choices, and improves my decision-making skills over time.

Decision journaling is a rare practice that takes very little time but pays huge dividends both now and in the future. Give it a try next time you’re facing a major crossroads.

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The Ascent

A community of storytellers documenting the journey to happiness and fulfillment.

Todd Lincoln, MBA

Written by

Stock-market investor, battle-scarred entrepreneur, and fireside philosopher. Creator of Investor’s Handbook:

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

Todd Lincoln, MBA

Written by

Stock-market investor, battle-scarred entrepreneur, and fireside philosopher. Creator of Investor’s Handbook:

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

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