How (and why) I went from being a night owl to waking up at 5AM

I was born in the mid-80s, so I’m about as “90s kid” as you can possibly be. I grew up loving Nicktoons and TGIF, eating Dunkaroos and drinking Surge. I loved my SNES, but eventually became a Playstation kid. I may or may not have dreamed of being a Ninja Turtle.

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And so it began … (me on the right)

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But when I was a kid, around 10 PM each night Nickelodeon (a landmark of 90s kids TV entertainment) switched its programming from kid-centric shows to classic TV reruns. They called it Nick-at-Nite.

Being a bit of a night owl even way back then, I was introduced to the likes of I Love Lucy, Bewitched, Happy Days, The Dick van Dyke Show, and Mary Tyler Moore.

I don’t imagine Nickelodeon had me in mind when deciding to rerun these shows in the late night time slots, but for some reason my brain just didn’t want to fall asleep until around 2 AM (at the earliest). So from as far back as I can remember, when possible, I’d be awake late into the night, and sleep late into the morning.

My parents hated this. They told me I was wasting the morning hours sleeping. I figured I was getting plenty of sleep still, just in a different block than everyone else. Obviously, school made this more difficult, but most of my summers were spent in this cycle, staying up late watching Laverne and Shirley or Dragnet, and rolling out of bed somewhere between 10 AM and Noon.

This sleep cycle continued into adulthood, as I chose night school for my college education, and every one of my jobs allowed me to set my own schedule.

I’m telling you this because I feel like I need to establish my night owl bonafides. If there ever was an unlikely candidate to advocate for waking up super-early, it’s me.

The Problem

I’m not going to sugar coat my point here. I didn’t see a problem with my schedule. But in hindsight, I see a lot of laziness in choosing this schedule.

Waking up late was easy. Which made staying up late easy. Which made waking up late easy. And so on.

It took no discipline. I didn’t decide to keep this schedule, I let the decision be made for me.

Maybe as a kid you can overlook that. After all, it was summer break. I had no where to be, and I wasn’t hurting anyone.

But as an adult, this lack of basic discipline had a radiating effect on other parts of my life. My sleep schedule was very clearly a negative keystone habit.

[Keystone habits are] small changes or habits that people introduce into their routines that unintentionally carry over into other aspects of their lives.

The Power of Habit, Charles Duhigg

But it was by no means the worst thing I was doing. I had a plethora of other bad habits, and I needed to address those first.

But once I had made significant positive changes in other areas of my life, I had one last mountain left to climb. But why this? Why change my sleep schedule.

But, Why?

In late 2018, for the first time in my life, I was becoming genuinely interested in my career. I was well out of my 20s, and I started thinking more seriously about my future, and what I wanted out of life. My job plays a huge role in enabling the kind of life I want to live, so focusing on professional growth was becoming essential to the choices I was able to make personally.

So I needed time. Time when no one else was around, and I could focus on getting stuff done.

So I figured I’d do my deep work after the kids were in bed. After all, I was a night owl. I could work for a good 2-4 hours each night between 10pm and 2am, right?


Turns out that after having been awake for the last 12-14 hours, my brain just didn’t want to work. This was “wind down” time, and I was trying to get things done? Nope. It never worked.

People who take offense at hustle culture are quick to point out that you don’t get “more time” by waking up very early. They insist that you have the same number of hours in a day whether you wake up a 5AM or 9AM. And they’re right. But in my experience (and definitely not ONLY my experience), those first few hours after waking up, after taking a little time to “wind up”, are BY FAR the most productive hours of the day.

Why is that?

  1. No interruptions: most everyone else is asleep.
  2. Maximum energy: you’re fresh. No afternoon slump, no late day brain exhaustion.
  3. Clean slate: you’re not putting out fires, but instead you’re able to define your own agenda and focus on future focused tasks.

After doing this for a few weeks, I noticed I was getting more done in the first 4 hours of my day than I used to get done in 8 hours before.

As a software engineer, this was a huge win for me.

But I was also able to accomplish some personal tasks in the early morning, too. I finally had the opportunity to try things like meditation and journaling. I could spend time reading, learning a new skill, or planning out a home improvement project. I could categorize the previous day’s spending in my budgeting software, while the purchase was still fresh on my mind.

I even watched a sunrise.

The benefits were clear. I still wasn’t a “morning person”, but I was starting to see the appeal.

But, How?

a man, up early, drinking coffee

So, this is probably why you’re here, reading this post. You already know the benefits of waking up early, you know you’re not doing yourself any favors by sleeping in late, and you want to change.

But you don’t know how.

I don’t claim to have the secret. Only what worked for me.

So, I’m not going to give a full course on how to develop new habits, I can tell you that, for me, the key was understanding the Cue > Craving > Response > Reward cycle.

Recommended Reading

Atomic Habits by James Clear

I’m not telling you that understanding this is going to be a magic bullet. Doing something you don’t want to do is going to take some discipline and willpower. But maybe we can exploit this natural part of human psychology to reduce the level of effort necessary to wake up early.

Here is my process:

The night before, I assemble all the necessary components to make a cup of coffee. I grind some beans, I prepare my pour-over brewer, and I fill my kettle. I set everything on the stove, ready for a single button press begin the process. I charge my iPad and I put it in my office, ready to browse Youtube.

My smartwatch is ready to buzz at 5AM the following morning. I use a Fitbit Charge because its battery life is 7 days, meaning I can basically leave it on all the time, charging it while I’m in the shower.

The first few days are hard. You haven’t yet connected the cue to a craving, but if you commit to NOT letting yourself have the reward if you don’t have the proper response, that connection will eventually form.

So, if you ignore your alarm and wake up late … no coffee for you. Literally walk to the kitchen and dump out the water and throw away the coffee grounds. Never, EVER reward yourself for failure.

But when you succeed, enjoy your reward.

For me, the connection happened quickly.

My wrist buzzes, and I pull myself out of bed.

Oftentimes, I actually wake up naturally about 5-10 minutes before my alarm. That’s a nice bonus.

I walk to the kitchen and start brewing my coffee.

For what it’s worth, the reason I use the pour over method for making coffee isn’t because I think it tastes better. I’m not even a little snobbish about my coffee.

Nope, the reason I use it is because it’s manual. I don’t have the option of having a timer make my coffee. I get to trigger my craving during the ~4 minutes it takes for it to brew. The method, each step in the process, the smell, the visual appeal … this all reinforces the craving that starts the minute my alarm goes off.

I take my freshly brewed coffee to my office and begin my day with a reward for making the right choice.

Once the caffeine kicks in, my day officially starts.

It only took a few days for the habit to form. And now I, Nathan Rice, a lifelong night owl, a Nick-at-Nite connoisseur, and someone who has absolutely no natural affection for mornings, am able to effortlessly wake up at 5AM every morning.

There’s no reason you can’t do the same thing.

If you want to.

Want to get ahead in your career? Cheat! (hear me out)

The most vivid memory of second hand embarrassment I have is from my high school Spanish class. We were taking our exam, so we were all a little nervous. Because exams were more heavily weighted than regular tests or quizzes, this could make or break your grade for the semester.

As our teacher, Mr. Wilson, walked around the room, we noticed him stop at Andrew’s desk. He slowly reached down and calmly pulled a tiny sheet of paper from under Andrew’s arm, examined it, and continued walking around the classroom.

student taking a test in school

Andrew’s face was bright red. He was visibly upset, and although it was, admittedly, slightly amusing to the rest of us in the class, we all knew what he was feeling.

Humiliation, disappointment … fear of what would happen to his grade.

In school, the rules were clear … this was cheating. He gave himself an unfair advantage. He wasn’t taking the test from memory, he had all the answers hidden under his arm. That’s just not allowed.

But you know what? You’re not in school any more. The rules are different at work.

We think the people responsible for our employment and promotions expect us to figure it all out ourselves, to have all the answers memorized like we did in school.

But that’s not true at all. At work, you get to “cheat”. As a matter of fact, you’re expected to.

Your Manager’s Perspective

One of my favorite questions to ask your manager is “what does it take to be a top performer in my position?” (from this book).

This concept blew my mind. It totally changed how I approached my job, my priorities, and my career.

It’s like walking up to the teacher and asking “what’s the answer to question 5 on this test?“, and most of us are just as uncomfortable asking our manager/supervisor this question as we would be asking a teacher in school for an answer.

The difference is, your manager is happy to just give you the answer. You get to “cheat”, and it’s totally fine.

The answer to that question, of course, will vary depending on your position, your manager, or the nature of your work. But there usually is an answer.

Once you have your answer, it’s up to you what to do with it. You can use it to agree to a later discussion about compensation or promotion, to build your resume, or to simply measure and track your progress toward your own goals.

Your colleagues’ perspectives

The single most impactful things you can do at work is to ask yourself, every single day, “What can I do today that would have the biggest positive impact on the business or the people I work with?”

I manage software engineers , so that’s the lens I view this question through right now, but I’ve had many jobs over the years: sales, bagging groceries, customer service, IT support, web developer.

No matter the professional context, your goal should be the same:

Help people.

But once again, it’s hard to know what will have the greatest impact, or who needs help, or how to prioritize your work.

So, cheat.

And be direct, no need to be sneaky about it.

“Is there anything I can do today that would help you get your work done?”

Flip the script

Sometimes it’s you who needs help getting unstuck, figuring out a tough problem, or handling a workload that’s too big for you. What can you do then?


Ask for help! You’d be surprised how willing people are to trade a little knowledge from their experience for an ego boost, or even a simple “thank you, I was completely stuck, so I appreciate the assist“.

Always show gratitude, always give credit, and you’ll very likely always have someone willing to step up and help you.

Andrew is fine, by the way

I’m not sure what happened after class. I’m sure there were some consequence, maybe even a failing exam grade. And I’m sure he hasn’t forgotten about the incident in Spanish class all those years ago.

But, he’s married with kids now, working as an accountant, and seems to be doing pretty well for himself. And I’ll bet he’s probably still cheating, only now he’s allowed to, expected to.

The rules are different at work. Are you cheating enough?

What does it take to be a great software engineer?

I spent the better part of the twenty-teens working as a software developer/engineer. To be honest, I paid very little attention to intentional professional growth during most of that span. We were a relatively small company, and I lacked the confidence and experience to think ambitiously. Being a great software engineer can be satisfying and lucrative, but not if you approach your career like I did.

Now that I’m responsible for a team of software engineers, I find myself in conversations that revolve around what success looks like, and the qualities of a top performer. And while there’s no such thing as perfection when human beings are involved, I have noticed some commonalities among the people that I’ve seen achieve the most success in the world of building software.

1. They’re honest

Being part of a team or organization means you have to be trustworthy. Without honesty, it’s impossible to build the kind of trust required to collaborate on a project. A reputation for not being able to accurately estimate how much time it will take to fix a problem or build a feature is a good way to ensure you never get the opportunity to do the kind of work that progresses your career and puts you in a position for growth.

And being in the habit of taking credit for other people’s work is far more likely to stall your career than it is to move it forward. Believe me, everyone notices that kind of thing, and it’s never appreciated.

2. They are curious

If you got into coding because you wanted a good job, that’s cool. I get it. Nothing wrong with that.

But if you lack the curiosity to explore new technology, experiment and try new (or newly learned) techniques, to leverage what you know to see what’s possible, you’re probably going to hit a career ceiling eventually.

Building software is a creative work, but it’s unique in that it is creativity in service of solving problems. Great software engineers embrace this work … relish it, even.

3. They communicate well in all directions

This isn’t unique to teams that build software. Communication is important in almost every line of work.

But when trying to coordinate engineers, support folks, product managers, marketing, and leaders up the chain of command, all while juggling the work and looming deadlines, good communication is a skill that instantly makes you stand out from the rest.

When working remotely (and I’d argue this is true for co-located teams too), a well written email or technical document is much appreciated by people from every department. It’s efficient (write once, share many times), effective, and can mitigate many of the issues that in person interactions present … like body language, tone of voice, misinterpretation, and our tendency to forget what what said in a conversation.

Master this skill, and people WILL notice.

4. They aren’t driven by ego

No one likes the one who brags about themselves, or steals credit, or exaggerates their share of the work.

It’s a terrible strategy, and it’s not the kind of attention you actually want.

5. They are driven to help

The exact opposite of ego, great software engineers are always looking for opportunities to help.

To help their team/teammates push a project over the finish line.

To help someone write better code.

To mentor someone through a difficult transition.

To share subject matter knowledge.

If you look around, there are always opportunities to help.

6. They leverage process

Great engineers tend to value efficiency. Why waste time arguing about an approach to a problem, over and over again, when you can spend a little time up front developing a value system that can solve problems for you?

Things like OKRs, the Agile Manifesto, team agreements, and even company values … these are all tools that good engineers use to deescalate touchy situations.

Recommended Reading

Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs

“That task doesn’t really help us achieve our stated objective for the quarter.”

“We can iterate. Let’s push this out and follow up ASAP to improve the UI.”

“That sounds like a good idea, but maybe it’s not necessary. Let’s ship what we have now, and get some user feedback before committing to do it.”

At Facebook, there’s a saying “Data wins arguments”. In other words, 5 people arguing from the perspective of their own individual gut feeling isn’t particularly effective or scalable. Instead, let’s just look at the data and save some time.

7. They care about their teammates

Things like peer reviews and 360 feedback have made it more important than ever that you develop an empathetic (and sometimes apologetic) attitude toward the people you work with. They’re human beings with complicated lives, and at any given time they could be going through something that makes work problems seem trivial.

Feeling trusted and supported can mean the difference between a good and bad day/week/month/year.

And when Murphy’s Law eventually circles around to you, you’ll be glad to have a teammate that supports you the same way.

But it’s more than just supporting teammates when they’re struggling.

Think about how much more valuable you are as an engineer if, by your influence and impact on your teammates, they get better at their job.

Maybe it’s teaching them a new skill they lacked before.

Or a trick/shortcut that saves them 2 hours per week.

Or a confidence boost that unlocks a willingness to take on a task or responsibility they would have previously avoided.

It could even be volunteering to attend a meeting and write up a summary for your team, instead of everyone attending the meeting themselves.

Recommended Reading

The Five Dysfunctions of a Team: A Leadership Fable

8. They enjoy the work

As I said earlier, becoming an engineer so you can have a healthy paycheck is totally fine. We all have bills to pay.

But this list isn’t about being “an engineer”. It’s about being a great engineer. And if you don’t really enjoy the work, you’re probably going to struggle with mustering up the motivation to do what’s necessary to continue learning, experimenting, and building great software.

This doesn’t mean you won’t have other interests, hobbies, and priorities.

But the likelihood of compartmentalizing “work” into a strict 9 to 5 box, and consistently growing as an engineer, is relatively low.

9. They’re “lazy”

A former boss used to say this about me all the time. But I was never offended.

“Nathan is lazy, but in all the right ways.”

I was never going to do something manually that I could have a machine do.

I was never going to waste time building something that I didn’t think had value. Or at least, I would have pushed back hard on it.

Having the experience and judgement to know what not to do makes you way more valuable than someone who just jumps into projects without giving it any thought.

This can come across as “lazy” to some, but it’s a good kind of lazy.

10. They get stuff done

Look, at the end of the day, you’re just not going to get very far in your engineering career unless you find a way to get stuff done. It’s the core of your responsibilities, and it’s what you should prioritize first.

Your job is to use code to solve problems, so the more problems you solve (without creating new ones) in the same amount of time or with the same amount of effort, the better.

Great athletes challenge themselves though intentional practice, to run a little bit farther or faster, to improve their accuracy, to perfect their form or develop new techniques, all in the pursuit of greatness.

Are you, as a software engineer, challenging yourself to work a little faster or a little smarter, to be more helpful and empathetic, to squash your ego and commit to honesty?

If not, what’s stopping you now?

When is the last time you said “I’m sorry”?

In December of 2012, I officially became a parent. Thinking back on those first years of my daughter’s life (before our other kids), it’s amazing the things you remember and forget (until something reminds you).

Now that she’s a bit older, I see that one of the easy things to forget is what a handful she was as a baby and young toddler.

We learned a lot in those early years, not the least of which was the fact that love and discipline, plus consistency and patience can be a truly magical combination for helping children navigate their emotions while building a deep and lasting bond with them.

A picture of me and my daughters from 2018
My and my girls, 2018

But the ugly side of parenting is that you are forced to come face to face with your own worst flaws.

The mistakes I made as a parent are too many to count, but one thing my wife and I committed to early on was that if we made a mistake with our kids … overreacting, losing our temper, unfair punishments, misunderstanding, misapplication of blame, incorrect assumptions … we would verbally apologize to our children. We would kneel down, look them in the eye, and say the words “I’m sorry, that was wrong. I should not have done that.”

It’s such a humbling (humiliating?) thing to have to do. Me, the parent, apologizing to them, the kid … it feels strange. But it does get easier the more you do it.

Since making this a part of our family’s DNA, it’s amazing how often you notice the mental gymnastics some parents perform to avoid saying “I’m sorry” to their kids, and it’s a good reminder to me how important that small act, that simple phrase, really is.

Instruction + modeling = behavior forming

The best leaders I’ve experienced in my life were great at explaining what needed to be done, and also having the discipline and character to do it themselves.

One of Andy Grove’s 5 responsibilities as a leader in High Output Management is “being a role model”.

“Do as I say …” just doesn’t work.

If you’ve been given any leadership responsibilities, modeling the behavior you want to see from your team is absolutely essential.

Owning Our Mistakes

One quality of a healthy team is adopting a culture that encourages everyone to own their own mistakes.

Sometimes that’s missing a deadline, or shipping a bug to production, or forgetting to do something that you committed to do.

Sometimes it’s being accidentally (or purposefully) insulting, or taking something personally that you shouldn’t have, or snapping at one of your coworkers.

A team culture that allows for mistakes and encourages speedy apologies is a health metric that is at the top of my priority list as a leader.

Recommended Reading

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

But just wanting that kind of culture doesn’t guarantee it.

Telling your teams that’s what’s expected of them, coaching them to be generous with apologies and forgiveness, giving presentations or recommending books … none of that will be as effective as them seeing you, the leader, practicing what you preach.


So, back to the title of this post: when was the last time you said “I’m sorry”?

Guess what? You’re not perfect. You do make mistakes.

If, for some reason, you believe that the reason you haven’t apologized lately is because you’ve done nothing worth apologizing for, you have bigger problems.

If you aren’t apologizing, it’s not because there’s nothing to apologize for. You’re just so out of practice that you’re not letting things register as mistakes worth apologizing for.

Make it a practice to notice and write down every time you mess something up. Every mistake is an opportunity to learn what not to do, and to model what should be done after the mistake was made.

Own your mistakes as fast as possible, so you can mitigate and correct the damage done, improve your systems to prevent it from happening again, and try not to make the same mistake twice.

Mind how you respond to others’ mistakes

After enough time coaching your team to own their mistakes and say “I’m sorry” when they make them, and of course modeling this behavior yourself, you need to make sure you are reacting properly when people actually start to adopt the practice themselves.

Is your team safe to admit mistakes in front of you?

One of my favorite interview questions to use when chatting with potential hires is “tell me about the last time you made a mistake at work that you had to apologize for?”.

I like this better than “what’s your greatest weakness?”, because for one, it’s unexpected, and two, there’s little room to wriggle out of it with a clever answer. No “I care too much” or “I work too hard / too much” nonsense.

It sets the tone for the team they’d potentially be joining.

It’s OK to fail on this team. Expected, even.

No blame, no bravado.

We apologize, we own our mistakes, and we get better. And most importantly, having the humility to admit a mistake in front of me will never be something you have to be afraid of.

Don’t believe me? You will when you see me apologize as much or more than anyone else.

How to tackle big goals by narrowing your focus with two simple questions

I made some poor decisions in my 20s. Or rather, a series of poor decisions that seemed to stack and compound.

I took on tens of thousands of dollars of credit card, student loan, and tax debt.

I gained 70 pounds since graduating high school, because I ate way too much fast food and pretty much never exercised.

I binged entire series’ of television shows while pushing work off until the last minute.

I would stay up late into the night, and sleep away the mornings.

And because of all this, my wife and I “had to” put off starting a family until we could get our house in order.

Add to all that a sense of angst over current events and politics, my tendency to stress over the security of jobs, the financial crisis that lead to The Great Recession, and a barrage of 24 hour news cycles that can mentally fatigue even the most psychologically resilient among us.

If you’ve ever been in a situation like this (or even just a fraction of this), you probably know the feeling of wanting a change, but feeling like there’s just too much. How do you figure out what to focus on, and what to ignore?

I needed a formula

I’m a big fan of using decision formulas for quickly analyzing things. They’re somewhat subjective, and will need occasional tweaking. But at their core, they can be really useful.

Because I had so many things that I let go off the track, I needed a way of focusing my effort … a way of identifying things that need ignoring, and prioritizing things that need attention.

So I borrowed a lesson from Stoic philosophy, combined it with a question that I often ask other people when they ask for advice, and came up with something that I have found quite useful.

I also inadvertently mirrored part of Steven Covey’s “circle of concern / circle of influence” model, outlined in 7 Habits of Highly Effective People. Oops! He probably says it better. Oh, well!

Question 1: Is this something I can control?

The chief task in life is simply this: to identify and separate matters so that I can say clearly to myself which are externals not under my control, and which have to do with the choices I actually control.

Epictetus, Discourses

There are so many things in my life that I can’t change. I don’t control the weather, I will not live forever, and certain people will just never like me.

But there are a lot of things that I can change. I can plan my activities around the weather, I can make choices that will allow me to live a bit longer, and I can choose who I spend my time with.

Only focus on what you control

Was I in control of banks when they were giving loans to people who couldn’t afford them? Could I control the stock market?

Do I decide if a client chooses to move forward with a project? Or how much money they’re willing to pay? Or if they’ll pay me on time vs. ghosting me after I’ve delivered?

Probably not.

But do I decide what food I put in my body? Do I get to choose how I spend my money? Is it my choice whether or not I get some exercise today? Or stay up until 2:00 AM? Or sleep in until 10:00 AM?

It’s a hard truth to accept. No one did this to me.

It wasn’t the credit card company’s fault.

It wasn’t the restaurant’s fault.

It wasn’t Netflix’s fault.

It was my fault.

These were decisions that I had made, habits that I had formed.

And after letting myself be angry at what I had done, I saw the silver lining: if my actions caused the problem, I was obviously the one in control.

Question 2: How much do I care?

If I decided that it was something I could control, I then have to have a difficult, honest conversation with myself. And I really had to be brutal about it. No aspirational answers, just the raw unpolluted truth.

Do I care enough to do whatever it takes to accomplish this?

When people ask for advice about the usual subjects:

“I want my kids to behave better”

“I want to lose weight”

“I want to get my finances under control”

“I want a promotion at work”

“I want to find love”

“I want to spend more time with my family”.

… it’s possible that they want it, but not badly enough to do what it takes to achieve it. And you know what? That’s fine. It may not be the right time, or there may be more important things that should take priority. The point isn’t to feel guilty about your answer, but to be honest with yourself.

Acknowledging the potentially painful parts of a decision can help us honestly analyze our desire for change.

So, I asked myself …

To have any influence over politics, my best shot was to run for some sort of political office. Was I willing to do that?


To fix my procrastination problem, I’d might need to give up my autonomy and get a regular job where I didn’t set my own hours. Was I willing to do that?

Again, no.

To fix my weight and health, I’d need to go on a diet and start exercising regularly. Was I willing to do that?

I tried, and failed, many times. Clearly I was not.

To fix my finances, I’d need to cut up the credit cards, sell a car, and go on a budget. Was I willing to do that?

Turns out, I was! What Now?


If the answer is “no” to either of these questions, it’s no longer my focus. It’s a dead issue to me. I won’t be wasting a single minute of effort or thought on it until/unless I can answer “yes” to both questions.

And when the answer to both is “yes”, it’s time to prioritize and focus.

And I mean intense focus. Maximum effort, focus.

I was able to leverage the ability and the desire to change, and give myself permission to ignore the things that don’t pass the test.

And maybe after I’ve conquered one goal, I’d be able to revisit my list from before. Perhaps my answer to the 2 questions will change once I have a win to reference.

So, what happened?

It took me 2 years, but I did eventually pay off all my debt, save enough money to buy a house, and develop good money habits that continue to this day.

And then …

After revisiting my list, turns out I was willing to take a job with a little less autonomy and a little more structure. Great decision, exactly what I needed.

In late 2012, I took on my weight and health. In 6 months, I lost 50 pounds, and I’ve kept it off.

In 2018, I completely revised my sleep schedule. I now wake up between 4:30 and 5:30 AM every day, and I’m able to get more done by 10:00 AM than many people do all day, including my daily budget analysis, reading, writing, etc.

Each goal accomplished sequentially, one at a time, and only when I could honestly answer each of the questions above with a confident YES!

None of it happened because of super-human discipline. If white-knuckle effort was the key to progress, I’d be hopelessly lost.

Luckily for me, it’s about eliminating the unimportant goals to make room for the ones that really matter, then letting the power of focus and compounding take over.

Autonomy, failure, and “pushing down”; what I’m learning about leadership

That title is a lot to digest, but as part of my (ongoing and never ending) journey to master effective leadership, it would be irresponsible not to cover the topic of autonomy.

Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives.

Daniel Pink, Drive

I’m still very much learning about the less obvious things good leaders do, and how to integrate those things into my own approach and management philosophy.

But here is one of those obvious things that didn’t take very long to learn: few things you in a leadership position will be more patronizing, more insulting, more humiliating than micromanagement.

Nothing says “I don’t trust you” quite as effectively as looking over someone’s shoulder (physically, or virtually) while they’re working on something.

But is it a necessary evil?

Trust and Patience

Imagine being truly great at a sport. Top of your game, physically able to achieve success, game after game.

Then slowly, as you age, you begin losing the power to impose your will with a ball. No longer able to run faster or jump higher, you’re forced to move on from playing professionally. At best, it’s now a hobby.

But then you get a call. A team wants to hire you to be a coach, to help pass on your knowledge and experience to the next generation of able bodied professionals, and hopefully achieve the same level of success in coaching as you did as a player.

Unfortunately, the reality is that very few great players ever become great coaches.

Why is that?

I can’t imagine how difficult it must be to know that in the not-so-distant past, you were so instinctively great at something, having the talent to make split-second decisions with a ball in your hand, seeing what needs to be done and having the ability to execute in real time, suddenly expected to watch from the sidelines, as a coach, during pivotal moments of the game.

To execute as a player takes talent and practice.

To execute as a coach takes trust and patience.

These are skills that you just don’t naturally develop as a player, but they’re essential as a coach.

Trust: to know that when your players leave the huddle, that they remember what you said, that they have the physical ability to make it happen, that they believe you can see what they can’t and will draw up a plan that puts them in a position to win. Oh, and they won’t allow momentary hubris to take over when it comes time to execute the plan.

Patience: to have a vision for what should be. To understand that no one wins 100% of the time. Having the discipline to see failure coming, letting it happen (when appropriate), coaching through the difficulties, and pushing your team to improve iteratively.

The best time to fail

I’ll admit that I have very little tolerance for my own failure. I figure if I think long enough about all the ways something can go wrong, I can mitigate them all. If I just ask enough questions, or do the most research, or have contingency plans for every scenario, nothing could possibly go wrong.

Not only is this an unreasonably heavy burden for a single person, it doesn’t even work!

Recommended Reading

Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong

Failure is inevitable.

So when is it appropriate to let your team fail?

How do we optimize our failure for growth?

Fail when the stakes are low.

If you play sports, it’s better to fail in practice, scrimmages, pre-season, and the regular season, than it is to fail in the last seconds of the championship game.

If you’re a carpenter, it’s better to fail when building a birdhouse than it is to fail building an actual house.

You don’t run a marathon without training.

You don’t attempt to free solo El Capitan without first trying it with all the necessary safety gear.

Failure is the best teacher

I still remember the single question I got wrong on my written driver’s test when I was 15 years old. I’ll never forget it. I have no idea what questions I got right, but the one question I missed is forever carved on the inside of my skull.

Better I get it wrong at a desk at the DMV than behind the wheel, right?

And that’s the point. I missed it in the safety of a classroom. The stakes were low. If I failed the test, I’d go back home, study some more, wait a couple of weeks, and try again.

If I missed it on the road, I could end up in the hospital (or worse).

“Pushing down”

My friend Katie (who doesn’t blog) asked a great question in a recent meeting we were in.

“Is it possible to push any of these decisions one level down?”

Katie Childress

She wasn’t suggesting we push every decision all the way down. We can’t ignore the reality that not everyone in every position has all the context needed to make the right call.

Her point was that we sometimes forget to even consider if it’s possible to allow a decision (case by case) to be made by your team, rather than you, or your boss, etc.

Are we asking the right questions? What are the risks? If they fail, if they get it wrong, what’s the worst that could happen?

It’s a lot easier to “push down” a decision when the stakes are low. If they fail, so what? We learn a lesson, we course correct, and we try again. Repeat.

As repeated failure teaches us what not to do, success becomes a more and more likely outcome.

This is how your team earns trust, and learns to trust themselves, for higher stakes situations.

This is how your team can fail productively.

Which brings us back to autonomy

Throwing your team into a high stakes situation, with no experience, and expecting them to know what to do, how and when to do it, and thinking they’ll succeed (under the guise of “autonomy”) could be devastating to both your business and to the team’s confidence.

Being a good coach is about preparing and equipping your team, in low stakes situations, to have the confidence and competence to succeed in the critical moments of their work.

Don’t waste the low stakes moments.

Put ego and fear aside.

Let them try, and sometimes fail.

Then watch with pride as they pop open the Champaign bottle, hoist the trophy, and celebrate a hard earned victory.