WoW 075: On getting started (part 2 – knowledge workers series) [Words of Wisdom]

The difficulties of starting

It is difficult to see how successful you can become when starting something new. It's unclear how valuable something will become when you are just setting out.

When you're starting something new, it can be uncomfortable physically, emotionally, and psychologically.

Physically, learning something new can be awkward to do something you've never done before, and it can be tiring to put in the initial reps of effort.

Emotionally, learning something new can be overwhelming, confusing, or even tiring despite it being thrilling.

Psychologically, learning something new can be intimidating or even seem threatening because of fear of the unknowns ahead or your self-talk and narrative about the topic.

Instead of having self-talk that limits your beliefs about your identity, try to use 'in-process' language. Language gives you a map of your world, so intentionally changing your language can help how you think about and navigate what you are trying to implement.

"I'm not a writer" or "I can't journal" is very different than "I'm starting to develop a writing practice," "I'm learning how to write," or "I'm starting a daily journaling practice where I write a minimum of one sentence each day."

"I'm not an athlete" is very different from "I'm learning a new skill" or "I'm enjoying a new sport."

That one sentence a day can grow into a powerful practice of self-reflection. The fun you're having with a new sport can result in surprising yourself with what you can accomplish.

When starting out, there's so much you don't know, and you don't know what you don't know. However, you can use this to your advantage. If you stay curious when starting, you can be open to new ideas and run experiments that an experienced practitioner wouldn't even think of or would 'know better' than to do. This can lead to surprising new benefits and breakthroughs. Experimenting doesn't feel too risky when you're just starting something because you have yet to invest too much.

But having little invested in what you are learning can also make it easy to stop too soon. So start by putting some skin in the game, having something to lose, but commit to the smallest specific tasks you can repeatedly do.

Develop things into a practice by committing to the smallest effort you can complete daily. To start journaling, commit to writing one sentence. Some days you'll write a lot more, and some days one sentence will be all you can muster. To start working out, do just a few minutes of movement or go on a short walk. Slowly build from there once what you're doing feels easy.

Keeping a streak alive is a powerful motivator.

Whatever you can easily accomplish, write down your commitment.

Then tell others what you're committing to, and ask them to check in with you on how it's going.

The dangers of success

What's more, once you reach a certain level of success, it can be tempting to try to minimize risk, avoid feelings of vulnerability, and stop experimenting with new ideas.

Once you reach a certain level of success in any sphere, it can be tempting to appear like you know more than you do. It can be tempting to stop trying new things, to not be a beginner at something, to not explore new areas of learning, or to not stray too far from what got you successful in the first place.

But learning requires exploring and experimenting. The most profound growth comes from play and curiosity. Starting something new and meaningful always requires facing uncertainty.

So don't take yourself too seriously; keep playing, experimenting, and exploring.

Instead of avoiding and minimizing exposure to new ideas and new ways of trying things, embrace them. The best learners are curious and do not have their egos tied to how much they know about a particular topic. Even if they are considered an expert, the best learners remain curious, wanting to know more, humbly aware of the vast amounts yet to learn. The more you know, the more you know how little you know, and the more you forget how much you have learned!

Experimenting with change

What if you thought of starting something new like running an experiment?

Choose a hypothesis, and then ask yourself: what experiment can I run to test out my hypothesis? Then give it a go.

Measure your progress and whether you're proving the hypothesis or have proved it wrong.

Seek to intentionally complete cycles of running that experiment so that you can continue to learn and tweak future experiments. In the world of startups and software development, it's called build-measure-learn.

The key to this concept is starting with a hypothesis and then going through a learning cycle of running an experiment to verify this hypothesis. This mental model can be a helpful strategy in many different situations.

Here are a few more suggestions for implementing this build-measure-learn concept.

Instead of committing all your time or money to one thing, cycle through a few experiments to test out which thing works best before committing more time or money.

Identify what you want to measure as you move through the cycle.

Think about how you can move through the build-measure-learn cycle quickly and efficiently.

Review what you have measured and try to learn from it, either updating your hypothesis, reinforcing it, or scraping it completely.

Whatever you learn, by thinking about running experiments, it helps externalize what you do from your identity, so it can help you take risks that you might not otherwise want to take.

Write it down

Finally, I strongly recommend you write out your commitment and your hypothesis, what your experiment will be, and keep a journal on your progress. The simple practice of writing things down can be immensely helpful.

Journaling your progress could mean tracking whether you did the task each day. Or you could have a weekly journal prompt: "What am I learning?", "What is going well?" and "What is not going well?" to help you reflect as you go. Journaling about your progress externalizes it, gives you a resource to review in the future, and helps cement the practice you are developing.


Identify what new thing you want to start or what new direction you want to head. What is the smallest thing you can commit to each day to grow in this new thing? Who can you tell about your commitment?

With your current problem, what initial hypothesis and experiment can you run on that hypothesis?

What will you measure? The practice or habit itself? Key metrics for success? What you are learning?

How can you move through the learning cycle quickly?


I'd love to hear if you are starting something new! Just reply to this email and let me know. Or share this email with someone and tell them what experiment you are running.

Live wisely,


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