Entrepreneurs are obsessed with freedom but the really savvy ones figure out that routine is what actually sets them free. 

The structure and ritual of highly optimized routine is the foundation that entrepreneurial freedom is built on.

By Peter Shallard Commit Action CEO | The Shrink for Entrepreneurs

To achieve true freedom, an entrepreneur must first put themselves into a state of ultra focus and effectiveness. 

Winning the kind of “escape velocity” that allows you to do anything with your life only happens by producing significant business wins. Massive value creation – no matter what your industry – requires you to make it happen. And to do that? You gotta push yourself to focus and execute. 

This is where routines help…

  1. Routines create focus and turn you into a high leverage entrepreneur. 
  2. High leverage entrepreneurs create massive value. 
  3. Massive value creates a lot of options (aka “freedom”) for the entrepreneur. 

The tremendous power of optimized routines is precisely why mega-successful business owners are obsessed with their morning rituals, their day-to-day meta work structure and all manner of productivity frameworks. 

As an entrepreneur, you should experiment with routines to find the rituals and cadence that suit your personality and that also suit the outcomes you’re pursuing. 

Once you’ve found a ritual that reliably and repeatedly makes you the best version of yourself, the next step is to institutionalize it. What makes a routine a routine is you sticking to it. 

The obvious, well known routine tactics are mandatory: 

  • Use some kind of physical reminder to start the routine off, like leaving your running shoes on top of the toilet seat as the first thing you see in the morning. 
  • Reward yourself for sticking to the routine. 
  • Start small. 
  • One routine at a time. 
  • etc etc etc

Those are the fundamental basics, but here are five much lesser known – and much more powerful – tactics for making your routine stick:

1. Tie a new routine to one you’ve already mastered

Once a new behavior is ritualized and made into a true habit in your life, it’s vastly easier to augment and add to that habit than it is to forge a brand new one. 

The reason for this lies in the structure of your neurology; the way the human brain links up thoughts and experiences. You can think of any routine you’ve genuinely made a habit of as a “well worn pathway” in your brain. It’s easier, faster and more reliable to add a few steps to a pathway that already exists than to do the mental equivalent of striking out into the jungle without a path at all. 

At the simplest level, this means that attempting to develop a routine like “daily stretching exercises” is best added to – and on top of – an existing workout routine or gym habit. 

Less obviously, you can tie a new optimized entrepreneurial routine to your existing normal-life habits. A terrific hack: Add reading twenty five pages of high quality non-fiction to your morning coffee or breakfast routine. 

If you’re the kind of person who has a good email management routine and regularly hits the coveted “inbox zero”, you can use doing exactly that as your cue to send out a proactive new connection email, or to cross-introduce valuable people within your network. Tie working through your email itself to a new proactive routine of building out your sphere of influence!

If you have an existing journaling habit, it can be morphed and extended to a content-creating habit: Just switch from writing for you after you’ve done a few hundred words, and start drafting with your customer in mind. 

Even bad habits can be highjacked and re-directed: Every time you catch yourself flipping over to social media feeds and consuming random internet content or news, don’t beat yourself up about it! Instead, try keeping a valuable business book handy and flip it open instead. Turn your distraction seeking habit into one that actually serves you! 

2. Leverage gamification with meta-measurement

Here at Commit Action we’re constantly helping our members with a frustrating bug in the software of the human mind. We call it the Action-Result Gap. 

This Gap is the initial period of time on a new project or routine where you have to lean in and push yourself to execute, despite the discomfort of doing so. And when you do, your reward is a long period of absolutely ZERO results arriving from your efforts.  

For example: 

If you start a routine of working out and eating well, it’ll be three to four weeks before you notice any actual changes in body weight or shape. That’s a long time for the brain to stay motivated without a positive feedback loop that keeps you inspired. If you could eat a salad and immediately see a your waist lose an inch (i.e. a very short Action-Result Gap)… everyone on earth would have rippling abs! 

In the business world an entrepreneur might start a routine of cold calling, to sell into a new vertical that has a “sales cycle” of six months or more. That’s half a year of building relationships, follow up and connecting before any sale happens. The only way to get the final “dollars in the bank” result… is to push through that long gap and continue taking action even though it doesn’t feel like it’s working.

Giving up and quitting the action part – before you’ve bridged the Action-Result Gap – is a guarantee you’ll never get any result at all. 

The bug in the human mind is that we’re wired to be pleasure seeking. 

Our brains get highly motivated by tight, short positive feedback loops. When we can take an action and get a result immediately, it feels great and it’s easy for us to keep at it. This is why gambling (and donuts) are so addictive. 

The challenge of entrepreneurship is that it presents some of the largest Action Result Gaps humans ever face. 

And this is precisely why so few people succeed in business. 

Any valuable routine you’re trying to build as an entrepreneur –  be it focused on self-improvement, sales, content creation or even leadership – is going to require a tremendous commitment to the routine in the face of what appears like zero progress for the short and medium term… You’ve got to stay the course until the results start flowing. 

Gamification through Meta-Measurement is the only “hack” that side steps the challenge of the Action-Result Gap. 

Meta-Measurement builds a game out of the routine itself, creating a psychological reward for the behavior that’s being optimized for… rather than just the ultimate result. 

This Gamification is understood and leveraged by the world’s best B2B sales managers who will regularly create rituals like a “Cold Call Challenge” for their teams, where a leaderboard for the number of initial appointments set with qualified prospects is proudly displayed. They’ll hit gongs, award silly prizes and make a great game out of tallying up the results as the team executes. 

The psychology of what is happening in this example is crucial to understand. 

Cold calling to set appointments to discuss a possible sale… is not making sales. It’s not even a guarantee of revenue. It’s a proximal step in the long term process of a sales person building a sales pipeline. That whole process contains an enormous Action-Result Gap. 

By creating a “Meta-Measurement” – i.e. the tally of cold calls made – the action at the FRONT of that pipeline is being turned into a game. This has a profound psychological effect. 

Meta-measurement and gamification create the shorter positive feedback loop that rewards the brain for the effort and struggle its making in the short term. With that reward in place, it’s much easier to continue pushing toward long term actual results. 

As an entrepreneur, you must add Meta-Measurement and Gamification to all routines you build in the service of your biggest, longest term visions.

If you’re trying to build an outbound sales routine, you can directly model the gamification described above. Meta-Measurement works even when it’s just a game you’re playing with yourself! And it goes for every other routine in business, too… 

Trying to write more? Commit to a certain word count each day and set up a wall calendar where you mark off each day you hit your routine goal. 

Set small rewards for yourself, for hitting streaks. 

Reading. Researching. Product Design. Leadership. Anything that has a routine and an Action-Result-Gap can be turned into a game by applying Meta-Measurement that turns the routine itself into the goal.  

3. Cultivate self awareness (and learn why your past routines failed) 

Routine building is one of the areas we see entrepreneurs make the “Insanity Mistake” more often than anywhere else. 

The Insanity Mistake is the old chestnut: 

The definition of insanity is doing the same things over and over and expecting to get a different result. 

Otherwise hyper-intelligent entrepreneurs will bang their head against the same wall, over and over, like crazy. They’ll try to build a routine, fall off the bandwagon and beat themselves up. Then they’ll re-commit, and just keep pushing away at it. 

Routine building requires grit and determination. But it also demands the self awareness to figure out that if it’s not working out, there may be something deeper going on. 

Psychologists have specific frameworks for increasing self awareness by asking precise, probing questions. You should know these questions and apply them – with radical self honesty – when your initial efforts (and perhaps secondary attempts!) to install a routine in your life have failed. 

  • What will this routine ultimately gain for you? 
  • What secondary consequences or side effects could building this routine have in your life? 
  • How will you know when the routine is “paying off” for you? (Are you clear on the outcome the routine is intended to create?) 
  • What will this outcome get for you or allow you to do? 
  • What parts of your life help in supporting this routine? 
  • What parts of your life unintentionally undermine your routine? 
  • How empowered are you to change those dynamics? (from the question above)
  • How motivated are you to change those dynamics? (ditto)

Answering these questions often make entrepreneurs realize they’re chasing the wrong routines or trying to improve an area of their life that isn’t the real problem. 

One of the most common realizations we see is entrepreneurs who are pursuing a routine – like a certain morning ritual – that they’ve read about or heard as a good idea, but haven’t really thought through. 

This highlights the problem of gurus in the self-help space dispensing life advice to entrepreneurs like you, without any appreciation for the specifics and nuances of your specific business model and unique life dynamics. 

Often, entrepreneurs will also realize that different agendas, values and priorities in their lives are in deep conflict with each other… in a way that it isn’t immediately visible on the surface.

For example, a business owner committed to high level networking – leveraging their social life for business opportunity – will often struggle to build routines around things like health and “deep work” because they have a conflicting priority to stop whatever they’re doing to grab a drink with a valuable contact whenever the opportunity presents itself. 

This is okay and not even an unsolvable problem… but if the routines you’re building aren’t working out, it’s worth digging a little deeper with these questions to find out if any such conflicts exist. It’s too easy to compartmentalize your thinking and fail to be aware of inner conflict!

4. Don’t attempt to systemize your late afternoon or evenings 

This one is so straight forward and yet so many people ignore it or simply don’t know the truth: 

Our ability to “self regulate” – to control our thinking and push ourselves to execute on important things – is an ability we start the day with more of and deplete/diminish over time, throughout the day. 

Whatever you call it – conscientiousness, willpower, self control – pushing yourself to act on a routine or really anything… is something that takes mental energy and the human brain appears to have a finite daily supply. This is an assertion supported by considerable research and if you’re an entrepreneur building powerful routines, you’re crazy not to factor this into your planning. 

The golden rule is that you’re simply more likely to have an easier time being disciplined the earlier in the day it is. After you’ve properly woken up – which is easier for some than others – your best chance of implementing bold new routines and making them stick starts to gradually drain away. 

If you want to commit to a daily practice, start it as close to first thing in the morning as you possibly can. 

Accept and acknowledge that new routines are likely to fail if you’re trying to build them in the late afternoon and evening. 

5. You’re crazy to do it alone

(A.K.A Leverage external and objective accountability) 

A shocking body of research emerging in the last thirty years points towards the massive power of social interaction to optimize human behavior. 

Behavioral psychologists, neurologists and – most interestingly – even economists have demonstrated via study upon study that people perform substantially better when they’re “under observation.” 

It’s not just the scientific scrutiny of a researcher in a lab coat that makes folks do better at things like losing weight, focusing on problem solving, saving money or anything else. Social interactions and one-to-one accountability also provide a tremendous boost to any human’s ability to push themselves to accomplish huge things. 

Entrepreneurs have an isolation problem. 

The tech that is empowering a massively growing segment of the white-collar workforce to go freelance or to start their own businesses… is at the same time making people more socially isolated than ever. 

It’s entirely normal now – and for the first time in recorded history – for a successful entrepreneur to spend an unusually busy week (or month) almost entirely at home… and effectively alone. 

The “work-from-your-laptop-in-your-pajamas” dream is the most socially isolated work style in existence.  

Chances are, if you’re a business owner who uses technology day to day… you’re living and working in a environment that is psychologically dysfunctional. 

The social interactions that our brains have evolved to rely on for performance optimization are either absent altogether or distorted via our modern day stand-in for community: Social media.

If you’re trying to push yourself to develop new, high performance routines… you shouldn’t try to do it all yourself. The world’s most elite entrepreneurs have teams of people supporting them, mentors, investor boards above them and advisors bringing accountability in laterally. 

What about you? 

Commit Action helps entrepreneurs develop routines – and become the highest leverage version of themselves possible – by providing objective and pro accountability via our Executive Aide for Effectiveness service. 

The first hire every entrepreneur should make is the person whose job it is to keep you in your zone of excellence. You can start here.