Transitioning from a Night Owl to an Early Bird

Like a lot of people in my generation, I’ve been a night owl for years.

It started in high school when I would stay up super late playing computer games and chatting with friends, and it just never really stopped.

I’ve known for years that I would be more productive, healthier, and probably more energetic if I made the switch. 

But it’s still a struggle. Not only does it involve changing habits I’ve had for years, it also means less time spent with my partner, a seemingly dedicated, lifelong night owl. She’s had sleep issues and mild insomnia her whole life. She’s also too stubborn to try to fix it. (Since she’s editing this, it’s okay for me to say that. Especially since she freely admits it.) While I can’t and wouldn’t want to change her or her habits, it makes it harder to change mine.

Our daughter, a budding night owl herself, goes to bed between 9 and 10. Since she stays up so late for a kid, it makes it even harder to have any free time afterward to watch the things we can’t watch when she’s awake and just be together. 

Those things helped push back the idea of transitioning from late nights to early mornings. At the end of the day, sleep was on the lower end of my priorities. Over the years, I’ve decided to make the change several times, but it usually only lasts for a few weeks. At best. 

So I just lived my life in a sleep deficit. Falling asleep on the couch after work but then staying up until 2 am after I woke for dinner. Drinking stupid amounts of coffee and soda during the day, punishing my adrenals to keep up momentum while I work. Things like that. 

To make things even more difficult for me, it’s not even just about going to bed early and refusing to stay up all night with my wonderfully stubborn girlfriend. 

I also just really love sleep. Even when I was in the Army and had to go to bed early, it was still nearly impossible for me to wake up at the ungodly hours they expected us to.

I can literally fall asleep anywhere at any time. For me, it’s just a FOMO thing. I choose not to go to bed so that I don’t miss out on time spent with my girlfriend and the mindless things you do to take your mind off work, i.e. phone and social media. 

But what usually ends up happening is: I fall asleep on the couch ➤ Melissa tries to wake me up to go to bed ➤ I grumpily ignore her ➤ she eventually falls asleep on the couch ➤ we both get terrible sleep until one of us wakes up at 4 or 5 in the morning to go to bed. 

Maybe she’s not the only stubborn one in the house.

With all the changes in self-perception, healthy habits, and increased productivity that I’ve been working on since being quarantined, sleep is the next big thing that I’m trying to change. 

But first, I have to stop thinking about work, which is quite a feat by itself.


🔺🔺 My brain constantly thinking about work. 🔺🔺

Shutting my brain down from work-mode to focus on myself and my family is a huge challenge for me. For a few months now, I’ve developed habits that trigger my brain to stop thinking about work. 

  1. I stop working when dinner is ready. That’s the first small trigger. Sometimes I stop working before we eat though, so then I have to read, go outside with our kiddo, or talk to a friend just to take my mind off of it. Otherwise, I’ll keep thinking of things to knock out before shutting down for the day. But whether it’s eating, reading, or catching up, the point is to step away from my computer for the rest of the night. 
  2. I meditate. Meditation used to just be a thing to check off each day, but now it’s become a truly valuable ritual in my day. It helps me to shut down while opening my mind. Sensory deprivation has increased its effectiveness. I’ve set up a cozy spot in our walk-in closet where there’s no light. It’s in the back of the house, so with my noise-canceling headphones, I don’t hear, feel, or see anything. It works!
  3. I journal. Like meditation, journaling used to be a chore more than anything, but now I look forward to it every single day. It allows me to unload, think through my beliefs and ideas, and has paved the way for serious introspection that has led me to a higher level of confidence and empathy than I’ve ever had. I talked a bit more about this in last week’s blog, ICYMI

These three things effectively help me stop thinking about work so that I can rest better. 


As far as going to bed at a decent time, I’m not putting as much pressure on myself as I have before to go to bed at a certain time. That hasn’t worked for me in the past. I try to shoot for seven hours of sleep, but I’m not setting any accountability goals like I normally would. I think that created too much tension, lessens the benefits of forming healthy sleep habits, and makes sleeping more difficult. It works for some people, but not me. Not yet anyway.

What I am doing is forcing myself to wake up between 6 and 6:30 every weekday morning. 

I’ve developed a two-part morning routine that helps prepare me for my day. First, I throw on some clothes and shoes and immediately go for a walk. It’s been pretty wonderful being able to wake up, get outside, and be active before starting my work day. I walk for about an hour, then I come home and get ready for Morning BIL

The second part happens after our morning show. Since I record it with a close friend, it’s difficult for me to disengage from that social action to focus on work. So after we wrap up, I work on my Captain’s Log, which are all the notes from the day before. (If you don’t know what I’m talking about, make sure you sign up for my Sherpa Newsletter!) I also look over my call notes and update anything there and check Slack to make sure everything is running smoothly with the team. Then it’s on to my CRM to see how my pipeline looks and start planning my day around necessary touch-ins and follow-ups. 

After those little check-ins, I choose a bigger project to work on. I find that focusing on something that requires intent and focus early in the day makes it easier to get through everything else later. I use my noise-canceling headphones, listen to the Focus@Will app, and work. If I continue working on small tasks, I quickly run out and then I don’t have as much reserve or motivation left for the more difficult or deeper stuff later. 

work late

It may be too early to say that it’s going to stick this time, but I’m doing and feeling great so far. I’m more productive, more energetic and healthy, and more focused. And I have more time in my work-day, which frees up some time later in the evening. 

Even better, I’m not nodding off on the couch while I’m supposed to be spending time with my family. Well, I’m not doing it nearly as often… For the most part, I’m able to stay awake until I go to bed. That’s been a nice change for all of us.

The thing that I am happiest about is that it really hasn’t impacted my relationship with Melissa at all. I guess that was something I was telling myself in order to not make a change. And of course, she’s as supportive as she’s always been when I need to make a change. Maybe someday she’ll even join me on this one. Crazier things have happened.