How Can You Learn from Your History to Succeed Now?

Do you ever make the same mistake twice or realize that mistake somehow feels familiar? Many of us fall into patterns that allow us to recreate those mistakes—even when we don’t want to. However, we can learn from our history. When we do learn from our history, we can increase our chances of succeeding now.

I start with quantitative data because that’s often easier for me to collect.

Technology helps me gather all kinds of data to learn from my past to succeed now. I collect my sleep, weight, and step data to become as fit as possible. In addition, I collect weekly, monthly, and yearly data about my business, all so I can learn from what’s worked and hasn’t worked.

Quantitative data isn’t enough. I also use qualitative data about how I feel about my work. Here are some examples: how satisfied I felt with my work, the client’s outcomes, and my feeling about the fee vs. my work and the client’s outcomes.

I use this data to improve and experiment. That means I need fast feedback loops to use that data for double-loop learning.

I don’t just examine the outcomes of my work (one loop); I also review the process of that work (the double loop). When we use double-loop learning, we question our assumptions.

I’ve offered three ideas so far:

  • Fast feedback loops with various data to remember and compare the goal to the data. (The longer the feedback loop, the more likely I might forget the goals I set.)
  • The actual outcomes.
  • Question all my assumptions about how and what I did.

We can examine everything for personal data because we can choose shorter feedback loops. But work data? That’s a lot more difficult. Here’s how you might start.

Three Suggestions to Use Double-Loop Learning at Work

The three suggestions are:

  • Time to make work decisions.
  • Create a minimum outcome to start small and get feedback.
  • Reflect frequently.

Consider the time you take to make work decisions. We can often make decisions that only affect ourselves quickly. But decisions that affect others? We often think we need more data for those decisions. (I’m thinking specifically about strategic decisions such as the project and product portfolio decisions.)

Instead of requesting more data to make a longer prediction, what if you asked these questions:

  1. If I currently make yearly decisions, what would have to be true to make quarterly or monthly decisions? (That condition of “what would have to be true” might include data or actions.)
  2. How much do I want to invest to obtain that data?

Those questions might help you create shorter feedback loops.

(There’s an interesting problem if your bureaucracy creates long feedback loops. In that case, consider the ideas in What Can You Remove?)

As you work on reducing the duration of your feedback loops, consider when you can see minimum outcomes. Do you have enough information to start your double-loop learning? (This is the idea of Tip 4: Start Small and Tip 5: Seek Some Feedback.)

When I started to collect data I could accumulate in one week and reflect on that, I improved my throughput. You might want to collect this data:

  • The decisions you make: how long it took you to make those decisions and your expected outcome.
  • Compare that to what happened.

If you create a weekly cadence of reflection, you might create an environment of double-loop learning, because you expect this data.

Customize These Ideas for Your Circumstances

These examples work for me but might not work for you. But, consider this big idea:

  1. Start by gathering data you think you need, and make sure that data is easy for you to collect. (You might need to go meta and work on making that data collection more straightforward.)
  2. How frequently can you see outcomes?
  3. Reflect as often as possible to help you see where to create more focused outcomes and practice your double-loop learning.

Many intelligent people, including Churchill and Santayana, have discussed that those who do not learn from history will repeat it.

You can use double-loop learning to learn from your history and choose what will make you more successful.


I’m leading a session at the Leading Complexity series of masterclasses: Modern Management: Position Yourself to Take Advantage of Complexity. Yes, it’s about the ideas in the Modern Management books, but you’ll recognize many of the ideas. Use this coupon for a 20% discount: ROTHMANFRIEND20. The sessions start in September.

The Q4 2022 Free Your Inner Writer workshop is open for registration. (If you don’t want to take the workshop now, that’s fine. Please use the workshop page to add yourself to the list for future workshops.Yes, I updated the workshop to reflect the Free Your Inner Nonfiction Writer book.

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Till next time,


© 2022 Johanna Rothman

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