How do you define the size and timing of your habit? Redesign your habits Part 2

Enrique Allen
6 min readFeb 1, 2019

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We all want to change our lives in some way, whether it’s to get in shape, pick up a hobby or learn new skills. If you want to get better at something beyond dabbling, the key is to be more intentional about the habits that support whatever outcome you want. In my last post, I talked about the importance of selecting habits that make sense for your unique context. In this post I’ll focus on defining habits that set you up for achieving your goals. I’ll mostly draw from my recent journey learning how to surf and also weave in some tips from managing Designer Fund and being a former Division 1 athlete at Stanford. Even though “a wave doesn’t care who you are,” I recognize it’s an incredible privilege to have the resources for hobbies like surfing. I hope some of the tips below can help you make any change, regardless of your situation.

Part 2: Habit Definition

Audit your existing habits

Many people feel like they don’t have the time to make changes in their lives. Especially if they’re working multiple jobs to put food on the table for their kids and are exhausted by the evening. One step that can help you free up spare time is to audit your existing behavior. Simply take a piece of paper and add columns for Monday through Sunday. Write out hour by hour what you do each day including when you sleep, eat, meet, commute and even go to the bathroom. Get as granular as possible. For example, I recently audited my entire schedule and shifted when I take meetings so that I could have as much time in the mornings for creative work. In addition, look out for potentially unconscious habits that you do like watching TV after dinner, always eating sweets after a meal or mindlessly scrolling on social media. I haven’t had a TV for a decade and I don’t log into Netflix because I know how easy it is to get hooked on a series and waste hours. Without more awareness, there are potentially dark habits and relationships that are sucking your time and energy. What habits could you replace that are draining or distracting you from the new behavior you want to adopt?

Make your habit as tiny as possible

Starting too big is probably the biggest mistake people make when they’re trying to change their behavior. It’s easy to have big aspirations and then give up after you hit a few bumps in the road. That’s why it’s important to break down your new desired behavior into smaller pieces. I recommend using a methodology called Tiny Habits by Dr BJ Fogg. Take something as mundane as flossing your teeth. Instead of trying to floss all your teeth every day, Fogg advises to start with flossing just one tooth. Another example is when I was first learning how to juggle a soccer ball as a kid. My goal wasn’t to juggle a 1000 times. I started off with just kicking the ball once into my hands and then repeating that. Then I would naturally increase to 2, 5, 10 etc each week. I remember vividly when I broke the count of 16 outside my house and was so stoked that I kept practicing until I could juggle more than I wanted to count.

Similarly, when I first set out to surf, I didn’t say my goal was to catch a huge wave, ride through a barrel or even stand up. Just going surfing once a week was the intention. Then I started to do smaller behaviors like packing my wetsuit, tying the board to my car, checking the weather and picking the beach ahead of time. All of those tiny habits supported the larger behavior of surfing. Dream big and execute tiny like my partner Dave likes to say. How might you break down your new desired behavior into a series of tiny habits?

Find an existing habit to stack on

Another strategy Dr Fogg recommends is to find a solid habit you already have and to do your new tiny habit immediately after. For example, brushing your teeth is a strong habit and can serve as a trigger for the new behavior you want — whether it’s to floss your teeth or drink a glass of water. A classic example for me is stretching. Playing soccer has been a foundational habit for most of my life. So whenever I step on the soccer field I automatically do a routine of warm up and cool down stretches. Another habit that my co-founder Ben and I have done for years is to meditate on Monday and Friday mornings. We built off the existing habit of going to our studio everyday and decided to meditate immediately after arriving, before starting work. Also when I was looking for an existing habit to support surfing, I chose Saturday because I normally take the day off from work like Shabbat. How might you sequence your new behavior to leverage an existing habit?

Pick a default time for your habit and pre-schedule it

Making a bold resolution like converting to the latest diet fad indefinitely is likely unsustainable. Starting or stopping things forever is extremely hard and also depends on your personality. I recommend making your habit time bound and not too far in the future. For example, at Designer Fund we have a weekly OKRs meetings and quarterly OKRs planning that support our annual roadmap. These default times help set a pace and give us constant feedback cycles to measure our progress. For surfing, I chose a weekly rhythm because it didn’t feel too easy or too hard. I liked how each week the clock was re-set. I wasn’t too concerned about the rest of the year, I just wanted to go surfing that week. In addition, be smart about when to schedule your new behavior. As mentioned, my default plan was to go surfing on Saturday mornings, no matter the conditions—so I didn’t have to think about it. The more you have to remember to do something new, the less likely you’re going to do it. Can you commit to a specific and recurring time for your habit?

Prepare to flow with your motivation waves

You’re going to fail to do your new behavior sometimes while it’s still developing into a stable habit. You’re going to get discouraged or simply not feel like doing the thing and that’s natural, you’re not a robot. Also you want to enjoy what you’re doing and not be too rigid especially if it’s a hobby or side project. The key is to not let any setbacks stop you from making progress. Majo wrote an insightful post here where she recommends defining habits you can do when you have high motivation and also simpler tiny habits when your motivation wanes, so that you have a fallback. For example, when I was recently in Argentina, it was impossible for me to go surfing but my fallback behaviors were to practice my freestyle stroke technique in the pool and work on my balance paddle boarding. I think it’s really important at first to define a repeating structure like the 100 Day Project to establish your new habit while also being ready to adapt to your shifting moods and environment. If you don’t feel like it or can’t do your new behavior, what else could you do to help keep you on track?

Free up time and energy for yourself by auditing your existing habits. Define specific tiny habits that support a time bound goal to help kickstart a change in your life, whether it’s to run a marathon or showcase your work at an art show. Use an existing habit as an anchor for your new behavior. Pre-commit to doing your thing so that it’s not a decision and more instinctual. Prepare for inevitable setbacks and flexible ways you can respond. In my next post, I’ll share insights on how to increase your motivation and ability while your forming a new behavior. Let me know if you have any comments or questions.

Thank you BJ Fogg, Majo Molfino, Dave Baggeroer, Tricia Choi, Peggy Ludwick and Blake Reary for the feedback.

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Enrique Allen

Co-founder of Designer Fund. Investor in design leaders like Stripe, Gusto, & Omada Health. Lecturer at Stanford dschool. Former 500S, Facebook Fund, Venrock.