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To Build New Habits, Get Comfortable Failing


November 5, 2021

By Rowan Van Dyk

To Build New Habits, Get Comfortable Failing

2 min

by Sabina Nawas

Most of us don’t wake up in the new year resolving, “This will be my year of failure!” But perhaps we should.

If you want to succeed at new habits, you need to first learn to succeed at failing. Sociologist Dr. Christine Carter says our success at adopting a new habit depends on our willingness to be bad at it at first. And no matter how smart or skilled we are, new habits — at least any worth pursuing — are going to feel clunky at the outset. We are more likely to falter than achieve an instant state of flow. Because our minds automatically steer us away from that outcome, we need to learn to fail in small steps.

Here are four strategies I discuss in my workshops and that many of my clients have successfully adopted for new resolve that won’t dissolve in a few weeks but will instead evolve into lifelong strategies for success.

Immunize yourself against big letdowns

Entrepreneur Jia Jiang was celebrating the new acquisition of his business when the deal collapsed. He knew that surviving rejection is a necessary skill as an entrepreneur, but he hated feeling rejected. Jiang decided to build his immunity to rejection by designing a 100-day series of small experiments where he was likely to hear "no." These ranged from asking to play soccer in a stranger’s backyard to asking if he could present the weather forecast T

You can immunize yourself against big letdowns by implementing experiments where you will fail in tiny ways. Don’t like public speaking? Your voice wobbles and you stumble over your words, feeling more self-conscious by the moment? Make your experiments small. Record yourself speaking one sentence and then watch the video, or simply ask one question aloud in a meeting where you don’t have to speak up. By exposing ourselves in small doses to the strength we’re trying to build, we are less likely to suffer serious consequences if we fail — and we might even triumph. With each step, we strengthen ur immunity to the downsides of a new habit, increasing our chances of acing it in the future.

Make a commitment — before you chicken out.

Our enthusiasm at setting big goals for ourselves is matched by our fear of failure down the road. We readily convince ourselves that today is the wrong day to get started — to write that strategy document or have a difficult conversation. But there’s a window of opportunity between when we dream of our goal and before our self-protective reasons scream at us to retreat. Use this window to make a commitment to someone else. For example, you might tell your peer with whom you need to have a frank conversation, “I’d like to discuss our approach to design. Can we set up time next week?” Or just compose an email that will accompany a daunting deliverable before even starting the project. By beginning with the email, we create momentum to get out of our heads and make ourselves accountable to someone else. Once the declaration is out of your head and received by (or scheduled with) someone else, it’s much harder to retract.

Publicize what you’ve learned.

As the saying goes, it’s not that you fall that matters, but how you get up. Similarly, when you fail in small ways, identify what you’ve learned in the process. We tend to evade the limelight (maybe even take a sick day or two) when we haven’t landed the perfect formula. Instead, amp up the advantages of learning to tamp down the shame of failure.

For example, one organization I work with has a “lessons learned” database. After each milestone, members of the team reflect on what they learned and create entries in this repository. Colleagues who work on the next project then review these insights before launching their work. Individually, you can reflect on your own learnings and share it with your team in a meeting or in writing — or simply have it handy to flip back to later on your own. Additionally, start with more tentative language as you test out new skills. Framing something as an experiment, beta, or draft places you in a learner mindset. It makes perfection unnecessary, allows you to move faster, and garner helpful feedback and buy-in along the way.

Keep a progress meter and allow yourself to stop.

The best way to progress from couch to marathon is not by beating ourselves up each morning we miss a run. Each time we shame or blame ourselves, we undermine our motivation to continue. Instead, track runs over time, rather than assessing each day individually. By keeping a log of your efforts, over time you’ll notice how far you’ve come. Additionally, stop when you’re at your peak — while you’re doing well with your new habit and still enjoying it. To know you’re stopping before your performance starts to decline, allot a time limit and don’t exceed it, or take note of previous days and identify when your mood changes from excited to deflated. This way, you will eagerly anticipate the next session instead of battling the blahs of a B performance.

Our habits and mindset implore us to think big but keep us stuck, fearing we won’t play big enough or well enough. Dipping our toes into failing small opens a path to lasting change. Switching habits is easier when the price isn’t steep failure, and the reward is big success.