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How to Wake up at 5AM and Build Your Startup

What does your morning routine look like? Mine used to be waking up at 7AM, sleep walking to the shower, frantically getting dressed into socially acceptable clothes, pouring myself a cup of caffeine, and walking amongst drones of zombies to a crowded bus station.

Of course, getting out of this hellish cycle is quite the “Catch-22.” The last thing you want to do after working eight-hours is to work on your startup. Yet, if you don’t spend time building your own business, you’ll be trapped in an endless loop of corporations. Racing to the office before 9AM. Managers breathing down your neck. An eternity of smiling at your coworker’s snide comments. Which is a horror movie in and of itself.

Via XKCD

Rise of the Morning Superheroes

So I decided to wake up at 5AM and build my startup before the soul sucking day of a gleeful employee started. And he lived happily ever after… would have been great! If I managed to wake up early the moment I decided to become a morning person. I quickly found that my half-awake zombified determination could power-through any obstacle blocking my sleep. On the lucky days I did manage to wake up, I would just sit there and stare into the abyss.

Productivity blogs make it look easy. You’re constantly bombarded with amazing feats that only these mythical morning people can achieve: 8 Things Every Person Should Do Before 8 AM, and 7 Things Morning People Do Differently, and Why Productive People Get Up Insanely Early. Watching these superheros catch falling airplanes before 8AM somehow makes you feel guilty for oversleeping. I mean are they even human?

Square/Twitter CEO Jack Dorsey
Wakes up at 5:30 to meditate and go for a six-mile jog. He kept up that routine during a period where he shuttled back and forth between Square and Twitter, spending around 8 hours a day at both companies.

The truth is waking up at 5AM is hell. Your “morning self” is not the friendliest of people. Mr. Morning Jekyll will subconsciously turn your alarm off before early morning meetings and snooze your alarm when you have to catch the morning train. You can’t trust yourself in the morning. So let’s appease your morning demon by changing how you wake up.

Find an Alarm Smarter than You

I’m not sure when the trend of being violently shocked awake took hold, but we seem quite content with our morning shock therapy. Instead of willingly accepting a blitzkrieg of violent noises, find an alarm that gradually wakes you up. Waking up slowly allows your body to accept the fact you’re waking up. So when your mind actually does wake up, you’ll be less in the mood of killing your innocent alarm.

You can use a coffee alarm that masterfully brews coffee to match the time you wake up. A light-up alarm that gently emits artificial light on your face while you reflect on how man has conquered the Sun. A vibrating wrist alarm to wake up early without having your spouse wanting to murder you every morning. Having a dog/cat/small-human walk over your face at 5AM is also a good option.

Personally, I use the “Warmly” alarm app alongside the default smartphone alarm. Slowly waking up to 5 minutes of birds chirping in your ear, before opening my eyes to Yo-Yo Ma’s Cello vibrating through the air is quite the morning experience. Outsmart your morning demon starting with your alarm clock.

Via Trn Tumblr

Have a Long-Distance Relationship with Your Alarm

Building a habit isn’t rocket science. A simple model of building positive habits (reading, exercising, socializing) and discarding negative habits (drinking, smoking, junk food) is through “Perverse Accordances.”

Evernote and the Brain: Designing Creativity Workflows
In design, you create affordances when you want your user to do something, and disturbances when you want them to not do something. Thus you encourage desired behaviors by making them easier, and discourage undesired behaviors by making them harder.

If you want to build a habit of “not” turning off your alarm, make turning off your alarm as difficult as possible. Set multiple alarms, download a puzzle alarm app, or place your smartphone in a jar. While I would love to cuddle my smartphone before I fall asleep and glance into its lovely glass screen the moment I wake. If you want to wake up early, move your smartphone far away and have a long-distance relationship.

Force Yourself to Drink Coffee

For those who survived the Hunger Games and actually woke up, staying awake is another problem. I mean you did just wake up at 5AM, why not go back to sleep? You have all the time in the world! You can always wake up early “tomorrow.” All the while regretting having listened to my morning temptations after falling back asleep. I’m simply a terrible person before my first cup of coffee. So let’s get caffeinated.

You can’t treat your 5AM coffee like a normal cup of coffee. It doesn’t matter if you painstakingly prepared a cup of hand-dripped Guatemala Starbucks coffee. If coffee is not part of your waking process Mr. Morning Jekyll will just ignore it. Don’t rely on your morning self to go out of his way to wake up. He’ll try everything to go back to bed.

Find a way to directly integrate your coffee into your morning routine. The goal is to make your alarm a “trigger” for your coffee drinking habit. “If” the alarm rings, “then” you drink coffee. Experiment on different ways to automate the coffee drinking process.

Initially, I planned on brewing a cup of coffee the first thing in the morning. I didn’t even make it to the kitchen. Then, I tried preparing a cup of ice-coffee the night before and placing it on my desk. I didn’t make it to my desk. Eventually, I placed the cup of coffee on my alarm (smartphone). So in order to turn my alarm off, I had to literally pick up a cup of coffee. Once the coffee is in your hand, you might as well drink it. Not drinking coffee at this point is just cheating. Treat 5AM as the start of your work-day, drink some coffee and build your startup.

Via David Olnick

Procrastinate Yourself Awake

Still not awake? A little procrastination never hurt anyone. Then again, self-professed Internet addicts don’t provide the best productivity tips.

I spend a ridiculous amount of time looking at funny cat pictures on Reddit, Imgur, and 9gag. Hopelessly dependent on my next viral fix. I just can’t help myself. Visiting the same website over and over again in hopes of new content. Consciously knowing there isn’t anything there.

So let’s justify our procrastination under a more productive light. While looking at funny cat pictures before you sleep, gives you temporary insomnia. Looking at your smartphone/computer first thing in the morning can actually help you wake up.

Why Screens Ruin Your Sleep
“Exposure to blue light of LED screens affects melanopsin, which leads to a suppression of melatonin, and ultimately keeps our bodies from feeling sleepy.”

If you can’t bear the thought of working on your startup first thing in the morning. Spend a few minutes procrastinating until your morning demons settle down. Remember, you’re fighting a two-front battle. Waking up at a freakishly early time “and” working on your startup.

Break Your Startup into Micro-Startups

When I can barely turn my alarm off, I’m not going to start my day debugging a server destroying bug. Your morning self is an asshole. Starting the day with a daunting task just provides extra incentive to go back to sleep.

By now I’m going to assume your New Years Resolutions has failed, like the normal 88% of us. One reason you probably failed is you chose too BIG of a goal. “I want to end world hunger” “I want to have a six-pack” despite never having exercised in my life. This isn’t a Miss Universe pageant.

“The Art of Manliness” shows how using micro-habits can help build towards a macro-habit. The goal is not to build your entire startup first thing in the morning, but to simply “start.” Once you get the engine rolling it’s easier to switch to a higher gear.

How to Create Habits That Stick
If you want to floss your teeth, just floss one tooth. Commit to flossing just ONE tooth — and make that your goal for the day. If you are able to do that, you’ve accomplished your goal. You can check it off your list. But here’s the trick: Once you perform the micro-habit enough times, it becomes much harder NOT to complete the entire habit than to simply do the whole thing.

Break your startup into micro-startups that you can work on in the half-awake hours of the morning. Build your app by writing one line of code a day. Start your blog by writing one paragraph a day. Build your portfolio by sketching one design a day. Build your startup in 100 small increments rather than spending 100 full-time days. Every work doesn’t have to be a Picasso. By decreasing the barrier to entry, you’re more likely to follow through and stay awake.

Build a Lean Startup

It’s hard to admit, but no one really knows what they’re doing at first. Even the largest startup unicorns in the world, took a long time to find their footing. AirBnb survived by selling political themed cereal Obama O’s and Cap’n McCain’s. #Slack came out of a failed game “Glitch.” Even YouTube began as a video dating service “Tune in Hook Up.”

Micro-startups work well with the Lean Startup methodology (The Lean Startup by Eric Ries). Not only are micro-startups easier to implement, but provide a shorter feedback loop that keeps you more in touch with your audience. With 75% of all startups failing, would you rather spend 100 days in a basement building a product your customers “might” like or connect with your audience everyday “while” you adapt your startup to address your customer’s pain-points? Don’t build another Blockbuster.

Start with the assumption that you’re wrong. Constantly validate your theories through micro-experiments. When I first started “Krown.io”. I explained the service as an “Annotation Blogging Platform.” That was, until I found out the majority of people have no idea what “Annotations” are. We tried a variation of “Smart Blogging,” “Highlight Blogging,” “Feedback Blogs,” and “Contextual Blogging Platform.” Which surprise, surprise. People still had no idea what we were talking about. So we added a bare-to-the-bones explanation, “Highlight a text and add comments directly on the highlighted text.” Validate your hypothesis.

Via SpaceX

Make Your Work Public

We all have that irrational fear the moment you publish your work, trolls all over the world will unite and make it their life’s mission to downvote you to oblivion. The truth is they don’t really care. In a world with 2 million blog posts published daily. Getting discovered is the bigger challenge. You really need stand out.

If you can’t even get yourself to wake up early and build your startup. Why worry about your content’s likability? That’s the same as worrying if you study too much you might become a Harvard Professor. If you’ve been struggling with your masterpiece for a while. The simple act of public accountability can help you wake up early and build your startup. Don’t just take my word. It’s supported by scientific evidence!

Does Monitoring Goal Progress Promote Goal Attainment?
Our findings are of relevance to those interested in changing their behavior and achieving their goals, as well as to those who want to help them, like weight loss programs, money advice agencies or sport coaches. Prompting people to monitor their progress can help them to achieve their goals, but some methods of monitoring are better than others. Specifically, we would recommend that people be encouraged to record, report or make public what they find out as they assess their progress.

You don’t have to build a interstellar satellite to broadcast your progress, simple tools like Twitter can help you wake up. Thomas Frank from the “College Info Geek” uses Twitter and Buffer in an ingenious way to force himself awake. Basically he sets an automated Tweet about donating $25 and has to wake up early to prevent himself losing $25. Trust yourself. Your work is interesting.

Be Obsessed with Productivity

Try to hit two birds with one stone and kill the third bird from shock. Making your micro-startup more productive provides extra incentive to wake up early. I start my day by writing a public journal. If I were just writing public journal for the sake of writing a journal, I probably wouldn’t be as diligent. A single journal helps build my startup in three ways.

First, writing a morning journal helps me reflect on my progress. How do I increase engagement with my audience? Should I switch over from Wordpress comments to Disqus Comments? Are Adsense ads still viable against the rising climate of Adblock? What is the best time to publish a blog post? What tasks can I automate? Am I crazy for starting a business?

Secondly, writing a daily journal builds content for my blog “Mynt.” Building a niche blog takes time. You need at least 1,000 short articles to begin gaining substantial organic traffic from Google. Writing a daily journal helps build the necessary content foundation.

Lastly, writing a public journal promotes my Annotation Blogging Platform “Krown.” Mynt is built on Krown and uses sentence-level comments to add contextual information. Every post on Mynt promotes Krown through the sub-domain “mynt.krown.io” and the CTA at the bottom of each post.

Prepare to Run a Marathon

Starting from 7AM completely switch gears to accommodate your 9–5 day job. While I would love to work on my startup full-time. Sadly humans are trapped in biological prisons where you to have to constantly eat, drink, and feel the urge to sleep with other people. Damn you Darwin. Working in micro-startups sprints in the morning, opens the possibility to continue working at your day job.

Be smart. Don’t bet your entire life on a single game of Poker. Allocate a portion of your assets to a life-changing Poker game, while working at the casino itself. Startups take time and you need to eat.

Based on the Barbell Strategy (Anti-Fragile by Nassim Taleb) you should allocate 20% of your resources to high-risk/high-return anti-fragile activities (ie. startups, bungee-jumping), and invest the remaining 80% in low-risk/low-return assets (ie. school, day job, family dinners). Experience the best of both worlds. Build your startup as a side-project first, gain validation, then jump into the unknown when you’re ready.

Wake up Early and Build Your Startup

Every morning startup routine will be different. Try to find a routine that fits your goals. If you’re going to spend 8 hours doing something you hate, at least invest 1 hour on something you love. Doing the same thing over and over again and expecting different results is madness. Don’t let your current “reality” drag you in the wrong direction. Face the odds, try to live the life you were meant to live. Wake up early and build your startup.


Originally Published with Awesome Sentence-Level Commentary!

Read the Fully Annotated Version at “Mynt.”

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