When creating new habits, let yourself be sloppy

"Don’t let perfect be the enemy of good" - Gretchen Ruben

One thing I have realized for myself, is that although I have an existing solid routine of great habits, I often expect that a new habit will also slot into the routine and immediately be just as solid. That’s a key mistake I’ve been making a lot, and I’ve recently adjusted my expectations.


It is often said that if you choose a specific time in advance for a new habit, then it can help you to be more likely to follow through. For example, if you tell a friend that you will go to the gym in the next week, compared with telling them that you will go to the gym at 7:30am on Tuesday, you are more likely to go to the gym when you are more specific:

"There are several key elements in building effective energy-management rituals but none so important as specificity of timing and the precision of behavior during the thirty-to sixty-day acquisition period." - Tony Schwartz

The flipside I’ve found, to this, is that if I choose a very specific time like 7:30am, then if that time comes by and goes, then I feel I have failed and the feeling of disappointment can stop me going at all, even though there is a lot of time left in the day. So, I try to combine this with a freedom to still go in the afternoon or evening and count that as success for my aim to create a habit, too. I let myself be sloppy with the timing of new habits, especially at the start.


Another key reason I found I sometimes failed with new habits, was when I made them into big things and then fell short. Or even worse, they were so big in my mind that I didn’t even do it at all.

As an example, if I decide to step up my gym routine and I aim to do 7 exercises, spending a whole hour in the gym, then some days I find that to be quite daunting. The problem with this is that it even stops me going to the gym for just a few minutes. What I do now instead is tell myself that if I go for 10 minutes and do just a single exercise, that counts too.

"the 20-minute walk I take is better than the 3-mile run I never start. Having people over for take-out is better than never having people to an elegant dinner party." - Gretchen Ruben

The interesting thing about this is that for the purpose of building new habits, going to the gym for 10 minutes is better than not going for 1 hour.

This blog post? it’s not as long as most I write. Both Gretchen Ruben quotes are from the same article. Yet, it’s still better than not shipping something this week.

Photo credit: Newtown grafitti

What is failure for you?

One thing I realised over the holiday period is that my definition of failure in a couple of things had changed considerably since the year before.

In particular, in the year of 2012 I built up my gym routine to the point where for the final 3 months, I went to the gym consistently 5 times per week. During the holidays, I “failed” with my 5 times per week routine, but this meant that I still went to the gym 2-3 times a week during that time.

Similarly with blogging, I’m now aiming to write 2-3 times per week, and so for me to “fail” with blogging means that I write once a week.

The role of failure and imperfection in building skills

Failure is part of success, an integral part. - Bill Walsh

I’ve written before that I believe imperfection is a key part of building habits and gaining skills. To sit down and decide a new goal or habit and expect to flawlessly go ahead and achieve it is unproductive. Instead, I think the best plan is to expect to miss the mark several times along the way.

The key to simultaneously expecting imperfection and not allowing it to get you down and cause you to bail on your idea, is perspective. For me, once I take a moment to realise just how far I’ve come, despite the fact I’ve failed at this moment, that’s when it’s easy to still be happy with that failure and then move forward towards being better the next week.

If you’ve been blogging once a month for 6 months, then you step it up to twice a month and achieve that for the first two months but fall short the third, don’t be too disappointed. Remember that eight months ago you weren’t even blogging at all, and this ‘failure’ probably just means you’ve blogged once a month. It’s always a process of gradual improvement.

Your failure is highly individual

We constantly compare our beginning to someone elses middle. Our middle to someone elses end. And when you do that youll find that youre never, ever satisfied. Youll never, ever be good enough. Youll always struggle to celebrate your accomplishments. - Matt Cheuvront

One of the hardest things I’ve found to grasp and be aware of, is that to each person, failure has a different definition. We are all at different stages, and our journeys are very different too. As Matt Cheuvront says, we’re always comparing ourselves to others when it makes zero sense to do that.

A most important thing with this, is that if you feel like you have failed with something, make sure that failure is your own and not someone else’s. If you’re hitting the gym twice a week and meet someone who is going to the gym every day, don’t let that make you feel like a failure. Our own goals and habits are completely individual to us. I think one of my biggest satisfactions comes from continually improving my personal bests, whether it’s running or lifting weights, blogging or speaking. Once you get into a habit of beating yourself continually, you can make some amazing progress.

Adjusting your definition of failure over time

The other fascinating thing I’ve found, is that in just one year you can dramatically change what failure means for you. You can go from your highest success scenario becoming your “failure” scenario. This is very encouraging for me. It means that for example, in a year from now I can gradually work towards daily blogging, and by that point my “failure” might be that I only blog 3 times per week, which is my current success scenario.

It was a reassuring thought for me over the holidays that despite the fact I felt like I was failing by not keeping up my routine of going to the gym 5 times per week, I was still going 2-3 times a week and this was a lot more than I was doing a year earlier. So, the key is to think about the line you are creating rather than the individual dots.

Do you often accidentally allow failure to get you down without realising how far you have come? Do you sometimes compare your journey to others? I’ve been a victim of these things before, and I’m working to change that, and make real progress in my own individual path. I’d love any thoughts you have on this topic.

Photo credit: Behrooz Nobakht

Focus on the line, not the dot

Yesterday I noticed the Who’s Hiring? thread pop up again on Hacker News. If you’re hiring, it’s a great place to share that fact. Since around half a year ago, we’ve been actively hiring and so I’ve made it a task of mine to post to the thread when it appears on the first of the month.

As I sat down to write the listing for Buffer in the thread yesterday, the writing came very easily. At the same time, those words I wrote on that thread have had a huge impact. The listing itself gained 11 points and was placed 2nd out of all job listings. In the hours that followed, I have received over 30 emails from super interesting people interested in joining the team.

One thing I realized is that the blogging is the reason that this happened. I’ve now written over 70 articles on this blog, mostly around 700-800 words. That’s over 50,000 words I’ve written, and I would guess that by writing that much you are only going to get better. That’s why it came so naturally for me to write that job listing.

How focusing on the dot feels

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You see, what I’ve found is that if I ever stop and try to focus too much on any single article, and try and have a massive impact with one specific article, it becomes very unfulfilling. Although there are one or two article which have had a tremendous impact for me, I had no idea at the time I was writing them.

The way I see it is that when you focus on the dot, you focus on your impact between one workout and the next. You focus on your writing between one blog post and the next. You focus on the quality of your code between one line and the next. This is mostly going to result in disappointment.

As Jess Lee theorised in Why Startup Founders are Always Unhappy, if we focus on a single point in time, we are likely to be less happy.

How focusing on the line feels

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I find one of the most exciting things to be thinking about the line I’m creating with my gym routine. Since I started measuring my bench press performance, I have increased the weight by fifty pounds in six months.

With almost every exercise I do at the gym, I put the weight up by a tiny amount each week. This happens every single week. One week to the next doesn’t feel like huge progress, but if I just extrapolate that trend out, it means that within a few months I am going to be lifting a further twenty or thirty pounds on the bench press. There’s no way I’ll be able to do that without having a higher muscle mass, so therefore in a few months I am going to be in better shape.

Start thinking about being a line

So, my conclusion from all of this is that personally I am much more focused on daily habits and consistency than any single point or any future goal.

Mark Suster said that he invests in lines, not dots. His advice for us as entrepreneurs is to treat our fundraising strategy as a line, not a dot:

dont allocate two months of each year to hardcore funding activities but allocate a regular amount of time each month to it like any other job function.

Ira Glass has a fantastic video which hints at this idea too:

There is a gap. That for the first couple of years, that you are making stuff, what you are making isnt so good. Its trying to be good, it has ambition to be good, but its not that good.

The most important, possible thing you could do is to do a lot of work. Do a huge volume of work. Because its only by actually going through a volume of work that you are actually going to catch up and close that gap.

Are you focused on dots when you might make more progress by focusing on lines, by thinking about consistency? I’d love to hear your comments.

Photo credit: FullyFunctnlPhil

6 things I do to be consistently happy

Now that it’s almost two years since I first had the idea for Buffer, and with the year and a half before that which I worked on my previous startup, I’ve started to notice a few patterns amongst the ups and downs that come with building a startup.

One of the most important things I’ve learned during this time is that I perform the best when I’m happy. It really does change everything. If I’m happy then I’m more productive when hacking code, I’m better at answering support, and I find it easier to stay focused.

I’ve found that there are a few key habits which, for me, act as great rituals for enabling me to be consistently happy. They also act as anchor activities to bring my happiness level back up quickly whenever I have a period where I’m not feeling 100%. So here are 6 of the things I do:

1. Wake up early

One of the things I love about running my own startup is that I have complete freedom to experiment with my daily routine.

Through experimentation, I’ve found that waking up early every day makes me feel most invigorated and happy. It gives me a great start to the day, and this almost always leads to a great rest of the day. Over time, I’ve found I crave that “early morning” feeling, a time I can do some great work and be super focused. Gretchen Rubin from The Happiness Project mentioned something similar a recent article:

"I get up at 6:00 a.m. every day, even on weekends and vacation, because I love it.”

Waking up early every day requires discipline, especially about what time I sleep. Right now, I have a sleep ritual of disengaging from the day at 9:30pm and sleeping at 10pm. I now love all aspects of this ritual and with it in place I awake at 6am feeling fresh.

2. Exercise daily

"We found that people who are more physically active have more pleasant-activated feelings than people who are less active" - Amanda Hyde

In the last three years, I’ve gone from dabbling with exercise to it becoming something I do every weekday without fail. At first I had no idea what to do at the gym, so I asked my brother, who’s a personal trainer. I then went a few times with a good friend and soon I was hooked.

Over time, I developed this into a daily ritual so strong that I feel a pull towards it, and by doing it consistently I feel fantastic and can more easily take on other challenges. I recently discovered that exercise is a keystone habit which paves the way for growth in all other areas. I’ve also found that it helps me to get high quality sleep each night.

3. Have a habit of disengagement

"The richest, happiest and most productive lives are characterized by the ability to fully engage in the challenge at hand, but also to disengage periodically and seek renewal" - Loehr and Schwarz, The Power of Full Engagement

As I mentioned earlier, a key way I am able to wake up at 6am is through my ritual of disengaging in the evening. I go for a walk at 9:30pm, along a route which I’ve done many times before. Since the route is already decided and is the same every time, I am simply walking and doing nothing else. This prompts reflection and relaxation.

Various thoughts enter and leave my mind during the walk, and I’ve found this to be very healthy. Sometimes I think about the great things I enjoyed that day. Other times I will realise a change I should make in order to be happier day to day. I also feel calm and relaxed by the time I return from my walk, and I can therefore go straight to bed and fall asleep sooner than if I been engaged in my work and had closed my laptop only a few minutes earlier.

4. Regularly help others

One of my most fascinating discoveries about myself so far this year, is how happy it makes me to help others. For some time I had been consistently meeting founders to help them with their startups without realising that it was making me so happy. Then when I read Happiness: A Guide to Developing Life’s Most Important Skill by Matthieu Ricard I connected the dots of when I was happy and the activity I was doing: helping others.

I read Ricard’s section on the link between altruism and happiness and everything clicked. Since then, I’ve been consistently helping many startup founders and it’s brought me much happiness through both the challenge of finding ways to help each person, and the feeling that comes when I help the other person discover ways to make faster progress with their current challenges.

If you’d like to get startup advice via email or Skype, get in touch.

5. Learn new skills

"Being in the moment, focusing completely on a single task, and finding a sense of calm and happiness in your work. Flow is exactly that." - Leo Babauta

One thing I’ve found during my time working on Buffer, is that a key reason I’ve been happy for most of that time is that I’ve consistently had new challenges to take on. It may seem odd that new challenges can equate to happiness, but it is the times when I’ve slipped into a few weeks of working on something I already know well, that have led me to feel less happy than I want to be.

I think a key part of why learning new skills can bring happiness, is that you need to concentrate in order to make progress. The “flow” state has been found to trigger happiness. In addition, when learning something new you are able to learn a lot in a short space of time due to a steep learning curve. For example, in the last two weeks I’ve started learning Android development from scratch and I’ve personally found incredible the amount I know now compared to nothing two weeks ago.

6. Have multiple ways to “win” each day

Since the above activities are habitual, many days of the week I actually accomplish all of them. If I succeed with all five, I have a truly amazing day and feel fantastic. I have goals for Buffer, and I have goals in my weights routine too. In addition, I try to schedule one or two meetings or Skype calls to help people each day. I do this based on learning from around a year ago through an interview Tim Ferriss had with Matt from 37signals. I’ve mentioned it before on my blog, but it’s so good that I want to repeat it:

"If your entire ego and identity is vested in your startup, where there are certainly factors outside of your control, you can get into a depressive funk that affects your ability to function. So, you should also, lets say, join a rock climbing gym. Try to improve your time in the mile. Something like that. I recommend at least one physical activity. Then even if everything goes south you have some horrible divorce agreement with your co-founder if you had a good week and set a personal record in the gym or on the track or wherever, that can still be a good week."

So if I start my morning with a gym routine, work on Buffer during the day and help two people during lunch, I have 4 chances to have a great day. It almost always works.

Are there any key activities or habits you’ve found bring you happiness? I’d love to hear from you.

Photo credit: iko