Zen Habits of an Entrepreneur

What Being Successful Cost Me

If I told you that starting my first business nearly cost me my family and my health, would you believe me? If I told you that despite raising millions of dollars, being named one of British Columbia’s top 30 under 30 entrepreneurs and eventually divesting my startup to a 100 million dollar company, I struggled with depression and anxiety, could you relate?

I’m positive some of you know exactly what I’m talking about. Or, better yet, you know exactly how it feels to achieve your goals yet are struggling to cope. I know this because, if the last decade of my life has taught me anything, it’s that human beings share an incredible number of similar experiences and thinking patterns.

I’ll spare you details for now (as I’ll be writing a blog about Mental Health later on), but let’s just say after nearly eight years of straight-up, non-stop hustle, I got a rude awakening. I was sick, my relationship was struggling, and I realized that I hardly knew my eldest daughter. Still worse, my passion for what I was doing was turning to shit; most days I felt like I was stuck between the proverbial rock…oh forget it…it just plain sucked. That left me with a choice: change something or lose everything.

When it All Became Too Much

Spinning around in my head was a non-stop debate that went something like: How the hell am I going to build a new business and find time for my family and myself? If I don’t spend every caffeine-infused waking hour on my business, will it thrive…or even survive? If I don’t start being more present to my family will I lose them? When I look back at those petrified moments, I realize that I was mostly freaked out that I’d never amount to much and be remembered as the guy who should have made it.

My friends and peers viewed me as a super-positive, and highly-motivated entrepreneur with the world as his oyster. This did not help as even though I saw myself that way I couldn’t accept that I now felt vulnerable and unworthy.

Photo Credit – Simon Migaj – Unsplash

Daily, I dealt with quite the load of self-destructive thoughts from that bad voice in my head. The voice of fear thundered louder than any god I could have imagined.

So, when I finally shared my struggles with friends, mentors, and even a counsellor, I was shocked to learn just how common my situation was. Much of this journey is expressed in my upcoming book where I’ll share my dark years and the steps I took to reprogram some very bad mental habits. This is an ongoing process, I’m still in it, but, in this post, I’m going to share how to recognize bad habits and tools that helped me develop the new habits that have earned me results so far.

How to Recognize the Warning Signs

How do we get to the place where we feel stuck, anxious and depressed?

When you’re focused on a goal and following a long-term routine —like starting a business, getting your degree, or raising a family, it can be hard to clearly recognize two things:

  1. Bad mental habits we took on over the years. Especially in our developmental years of 0-6 and habits, we may have learned inadvertently from our parents and others who influenced our lives.
  2. Just how much “stuff” we really need to “unpack” (aka work through) about our bad mental habits in order to re-establish good mental habits.

When we face major struggles or drastic changes in our lives, like a bankruptcy, a partnership fallout, losing a job, a divorce, or dealing with a life-threatening injury, we can realize our innate vulnerability, imperfections, and egoic tendencies. In other words, it is during these periods of struggle that is often when all those bad habits rise to the surface.

For me, it happened when I left my post as a CEO of the company I’d founded and moved my family from Vancouver to New York to work for my new partners.

How to Develop a Zen Way of Thinking

Step 1: Mental models develop early.

For the purpose of this blog, let’s call that narrative going on in our heads our Mental Habits. These Habits are essentially the thoughts we think and the stories we tell ourselves (aka the voice in our head also commonly referred to as our ego) in response to any given situation that we may face in our daily lives. But where did some of these stories we tell ourselves come from?

Human beings are hard-wired for survival. Our ego is designed to keep us alive and is always plotting our “survival” from the worst possible outcome.

There are two key factors to consider when we think about this:

  1. It’s 2018 and a freakin’ sabre-toothed tiger isn’t going jump out of the bushes and maul us to death – now it’s just our spouse, colleague or someone taking our parking spot that literally triggers the same our flight or flight response that once kept us alive;
  2. The habits we need for survival when we’re 5, 15 or 35 years old may be totally different.

We have a tendency to think in counter-productive ways to what’s actually happening in the present moment. Think about it. Not only have you most likely changed since you were a kid, but maybe you moved from the city to the countryside or vice versa. Your world, the one you are experiencing at any moment, is constantly changing and evolving.

Each situation breeds different mental habits. However, the culmination of past experiences, misunderstandings and our own intuitive process, shapes these habits. And they often come from the strongest and longest influences in our lives: our family, friends, and teachers.

Let’s say, to use an over-simplified example, you grew up in a house where yelling and screaming, or being hypercritical of each other was the way you communicated. Now, 15 years later, when something doesn’t go your way you find yourself habitually yelling and screaming at employees who aren’t doing what you want or being hypercritical of your wife or children.

Or, you were told by a teacher that because you’re from a small town in the middle of nowhere you’d never make it as an artist in the big city. A part of you believed this because you were taught that teachers, as an authority figure knew best, and you accepted that. Maybe you only believed it a little bit. Now, as an adult, you form your own resistance-based mental habit because every time something is challenging, the mental story you tell yourself is that you can’t succeed.  In this hypothetical situation, it’s not that you’ll necessarily recall the specific memory of your teachers words in each instance of doubt (although you might) but you could have developed the belief all the same and not even realize you have.

We form layers and layers of these destructive mental habits and mental stories throughout our life.

It hurts to fix them, so we don’t. Instead, in order to drown out the noise of that negative story, we’ve developed a laundry list of bad habits like over-watching Netflix, overeating, smoking, jerking off 5 times a day, avoiding difficult tasks or change —whatever it is that enables us to cope and mask the thought that we may need to change our way of thinking. We can stay in these patterns if our base of living remains somewhat stable and predictable.

Now, Let’s say your husband or wife wants a divorce, you were fired from work, or you’re just not excelling at the level you want – these events that rock our world or break us down can be viewed as gifts that hopefully force us to realize we must change . Or as I once heard “People do not change unless the consequences of not changing are far worse.”

There are many paths, courses, teachers, philosophies, spiritual practices that can work, but it starts with awareness. When you see clearly that you want to change you can start to improve one mental habit at a time.

Step 2: Press Pause

Pausing Can Help Deliver A Moment of Clarity To Determine What The First Step in Healing Will Be

Photo Credit Lopez Robin – Unsplash

When your mind is spinning with thoughts because it’s trying to find the answer to a circumstance you’ve “deemed” a threat or a problem the best thing to do is just take a moment of pause. There are no right or wrong answers. For some, it could mean a psychiatrist prescribing antidepressants,  it could just be going for a run,  taking vacation or even a hot bath with a glass of wine. It’s just a moment of pause. Think about it this way: you’re snorkelling in crystal-clear shallow water but you’re lost and panicking and kicking your flippers so hard that sand is obscuring your vision. Kicking harder does not result in more clarity, it results in more sand blocking your vision. You have to let go, pause, and let the sand settle so you can see more clearly.

Start with doing something you love, but test a few things out to see which can give you that momentary reprieve from incessant thinking and worrying.

For me, even though I was fully dedicated to continuing work at my company, after reflecting on the inherent difficulties I was trying to overcome – the ones that lead to my initial challenges with anxiety and depression, I decided to take my family back to Vancouver (from New York) and work remotely. Yes, this pissed off some people, and that sucked!

Moving home meant my wife and children were closer to their support system and I no longer had to ride a train for 2.5 hours a day; I had more control over my schedule and more support for my family.

Once I was over the fear of missing out by not physically being in the office every, I realized how much time I wasted each day on A) ineffective work, B) too many meetings, and C) the commute (which can be put to good use as well but I often just watched videos or scrolled social to distract my mind).

For a while, not having all the daily “busy” work I used to get caught up in lead me to a feeling that I can only describe as something like having “my right arm being cut off but I still wanting to use it.” In other words, I kept trying to do things I no longer could being remote and I hadn’t adapted and repurposed my time appropriately.  That feeling faded over time.

But changing locations doesn’t fix habits or mental patterns; It’s akin to the old adage “wherever you go that’s where you are”; however, it can offer (and for me it did) a reprieve and maybe some extra space to approach those bad habits in a way you couldn’t see before.

So that’s when the real work began.

Step 3: Start With One Thing

Fix One Thing First. Then Before You Know it, You’re Doing What You Originally Thought Was Impossible.

We celebrate when babies take their first step and say their first word. It’s a tentative act in another long challenging process but it’s also a monumental achievement. That’s one of the only times we celebrate baby steps…after that, I’ve noticed we have a tendency to forget the small victories on our journey and just want to get to where we’re going as fast as possible.

Like most people, my first instinct was to fix a laundry list of bad mental habits instantaneously. This approach is likened to getting super amped up your first week in the gym, going way too hard, and then missing your second week because you a were sore or injured.

Attempting to change bad habits can lead to self-destructive thoughts of “not being good enough” or “I can’t do it.” From that very first self-destructive thought, it’s a slippery slope back down the rabbit hole of negativity.

The agonizing and harsh reality is that you have to pick only one habit to solve first. Block and tackle. If you solve one, then you know you can solve another and before you know it, you’ve trained your mind and transformed your lifestyle in entirely new ways.

So How Do I Pick The First Habit to Change?

Hypothetical situation. Let’s say you smoke, you want to get out of debt, and you want to get in shape. Which habit do you think is easiest to solve first? For me personally, I would say stop smoking first. Why, because if you stop smoking, you automatically save money on cigarettes, and eventually, you can start working out more (or working out better). If you try and do all three at the same time you may get overwhelmed or mentally exhausted and before you know it, you’re sucking on another cigarette to ease the stress.

When You Want to Say or Do Something Self-Destructive, Train Yourself Do Something Else Immediately

When you consciously make a choice to change a mental habit, you’ll quickly become harshly aware of it. It’s frustrating as hell to keep “not improving” and reliving a mental habit you want to let go of but the more we do it, the more trust we build in ourselves, the better chance we have of curbing the habit.

We start to build trust in ourselves by doing one thing well first. Personally,  I made a choice to meditate for 5-10 minutes every time I caught myself doubting a situation or outcome. No matter where I was or what I was doing, I literally had to take action. Now, even though I still have negative thoughts all the damn time, I engage with them less often. When I achieved that improved mental response, I was able to tackle other mental blocks with more confidence. Or, just like the smoking example, if we successfully quit smoking, we believe we can be successful at something else. And maybe, when we’ve mastered 2 or 3 good habits, we believe we can achieve the goals we’ve always dreamed of.

Step 4: Trust Starts With Compassion For Yourself.

We all self-shame. I caught myself the other week in a pity party about how organized someone else was with their fancy meeting-request software and how many projects they were juggling and I thought: Aw shit, I’ll never be that good.

No one that I know ever got better by shaming themselves. There is a difference; however, between shaming yourself and being a little hard on yourself because you know you can do better (and will do better the next time). Shame makes us feel little; self-encouragement empowers. Visit all the gurus and counsellors you want—ultimately it is not their job to make you feel empowered. It is their job to teach you to empower yourself – to unlock to power you already have in yourself.

Accept that you’re not the best at everything. Instead, find the people who can support you in those areas you’re not as strong. Maybe it’s a book or podcast that you engage with or maybe it’s advice from a colleague or friend; either way, you build a support network of people who can do the things that you can’t.

Personally, I try to start my day by affirming to myself that I have the confidence and support to make it through anything I may encounter today (negative thoughts, people, circumstance) while also affirming that I’m “enough” right now, even if I’m feeling anxious or depressed and that things will ultimately work out.

You can personalize this in any way that suits your mindset and current situation – it’s not always a one size fits all mantra!

Step 5: Set up Something Sacred Around Your Habit.

When something feels “sacred” or “special” we are more inclined to do it. Sounds corny…works like a charm. Once I started working more from home I had to create both special time and a sanctuary to work on things that were important to me.

Let’s say, nothing you’ve gotten yourself to a place mentally where you want to write a book but you can’t find the time, or, when you do, you don’t feel creative. In my experience, the daily habit of writing even a little bit is better than the sporadic habit of writing a lot. Same goes for exercise, healing or meditation. So, create a sacred space in your house to practice something daily. Make it a daily ritual you love. If you love tea and candles, then use those in your space. This sacred creative space will signal you to start doing your ritual.

And yes, schedule it, honor it, and ignore those calls and emails until you’ve done your daily ritual.

Zen Habits, Wellness, And How The Cycle Works.

When I started getting small wins at curbing bad mental habits and creating new ones, I realized that investments in my own health and wellness provided returns in my home life and work life. Each aspect was interconnected. My companies and my family need me at my best so I need to take care of myself first and foremost—mind, body, and spirit.

Wellness isn’t just about sitting in steam rooms and meditating or dropping downward dogs, it also includes learning new things and developing knowledge on a variety of topics.

I have three companies right now and usually work 12-14 hours a day, but my bucket of work is not just “work” in the traditional sense. It is all the combined elements that make my work and life better. This includes listening to podcasts or audiobooks, exercise, meditation, taking courses and even taking time off. Someone might say, ”Oh, how do you have time to meditate or exercise?” My answer is, “How do you not?” My work suffers when I’m not doing things to better myself.

Okay, But Really, I Don’t Have Time to Exercise or Meditate.

I call bullshit. Tony Robbins says everyone can find at least 10 minutes a day to take care of themselves. How do you choose to use them?

As a former elite runner, hardcore training was eventually etched into the fabric of my being. If I wasn’t working out hard, I was agitated. As my companies grew, my workload increased and I was busy with my family. Eventually, I got run down and sick when I worked out too hard. Then I’d miss more workouts. It was an unworkable cycle but I had developed a rigorous mental habit of working out and my body expected it as it was addicted to the feel-good hormones that often come with exercise. It was hard to get rid of.

Then, even though I didn’t believe I could stay as fit if I exercised at home, I decided to take just 1 month to work out 15-25 minutes each morning or evening at home. Because I wasn’t driving to and from the gym, it literally only took me 15-25 minutes. I made it 28 out of 30 days without missing a beat. Felt great. Stayed almost as fit without all the bells and whistles of fancy gym equipment and created a new habit.

I wake up 15 minutes earlier than I otherwise would meditate and journal and I listen to my audiobooks when I’m driving or on public transit, and sometimes when I’m working out. There is always time. Just start proving it to yourself by choosing one thing first.

Low-Value to High-Value Thinking and Those Damn Stories We Tell Ourselves.

Once you’re in a better mental habit cycle and headspace, it becomes a lot easier each and every day to shift out of bad mental stories or low-value behaviours into high-value thinking and better daily habits. A low-value behaviour is like this: someone says or does something at the office that isn’t in line with what you were thinking. So you get all hot and bothered inside and react with anger, indifference or even worse—talking some shit about them to another colleague or sending out a combative email.

A high-value behaviour would be acknowledging that not everyone shares your opinions or beliefs and asking yourself how you can learn from this experience. Then, being co-operative in your response to either try to find mutual ground, seek to learn more from them and their different opinions, or just accept it and move on.

Some people think (and I was one of these people) that being cooperative in a debate is a sign of weakness or being taken advantage of. You all probably know someone who can’t admit they’re wrong. Jamming your ideas down people’s throats is not a sign of leadership; listening and collaborating toward the right end is.

Gut Checks, Course Corrections, and Support.

Now you’re rocking and rolling and don’t want to fall back into your old ways.

Your gut check is your internal compass to know you’re on track. The mind will analyze and rationalize everything, which can serve a purpose, but follow your intuition (your gut instinct) on things as well. I like to say, “First, feel it through, don’t think it through.”

After I’d battled serious depression and anxiety, I became acutely afraid of creating any stress or hardship in my life. Once I was in a better place mentally, I realized challenges and good kinds of stress are important for our development.

Just as we need to use our muscles, we need to use our brain. Challenges and stressful situations help us keep sharp. Muscles don’t grow without resistance and, in a similar way, neither does our brain. Remember the beginning of this blog post where I mentioned the anxiety inducing fight or flight response served as a survival tool? Well, it can be used to our advantage still. When we feel an anxiety trigger, it can be a sign that we’re about to experience something we won’t be comfortable with. I’ve found that sometimes means I’m on the right track—pushing my own boundaries and giving myself an opportunity to create something new.

It Can Take as Long to Wade Out of the Water as it Did to Wade In.

Your journey out of bad habits and low-value thinking and negative personal storytelling happens over time. Just because you’ve decided to change your thinking doesn’t mean you’ll be a person you hope to become overnight. It took years to shape and develop bad mental habits and as such can years to develop new ones – Everyone has a different individual process. Be patient on the journey towards any goals and intentions you set for creating new mental habits.

Closing Thoughts and my Own Daily Zen Habits

Entire books are written about these topics and with so much information out there that in a blog I’ve barely been able to scratch the surface of this topic. My hope with this post is only to crack open the door so-to-speak and give you some tools to take the first step towards better mental habits.

Photo Credit – Tim Goedhar – Unsplash

I’m not a Psychologist or Doctor and everything I’ve shared I’ve learned through my own experiences and personal struggles. If I’m striking a chord, great feel free to connect with me and ask any questions you may have. But, you may also resonate with someone else’s experience, or require professional help,  so I implore you to seek out other sources.

29 Zen Habits to Practice Everyday

  1. Daily walking meditations for 1 hour. Oh ya, just like those old-timers in the park. Exercise, meditate, contemplate, breathe in the fresh air, score some vitamin D and, if you walk in the morning it can even help out with your circadian sleep rhythms.
  2. Celebrate the people in your life. Someone killing it on Instagram? A competitors company is rocking it on Social? Don’t feel negativity or harbour resentment toward them. Resentment builds from harbouring negative feelings. Celebrate others and you will feel better about these situations for yourself.
  3. Listen well. Give people your attention. Be an engaged listener. Being a good listener is both kind and respectful and makes people feel good, and you might actually learn something!
  4. Habits are daily. To achieve anything, we have to work at it each day. Make your most important habits, mental or otherwise, a daily practice. But on the flipside, don’t beat yourself up if something doesn’t happen according to the “plan.” Shit happens—it’s life. Do you think I work out and meditate every day? OF COURSE NOT! But I do it every day that I can.
  5. Let go. Let go of what you can’t control. Focus your energy on what you can.
  6. Daily meditation. (sometimes twice daily) I try to keep one meditation session purely as a breathing meditation—no visualization. If I happen to have a second meditation I’ll focus more on visualizations and intentions.
  7. Unplug for a day for a week or even longer. Resets and refreshers are key to mental well-being and new ideas.
  8. Travel often. New environments and cultures help us gain perspective. On that note, sometimes just driving home a different way from work today can help you see something new.
  9. Wake up early. Mornings are for the soul. There is a quietness in the morning that is rejuvenating and the extra time for you is key. My mother taught me this one.
  10. Trust The Process. Oh, it’s some seriously scary shit to trust the process but what choice do you really have? Don’t worry about what you can’t control; trust that if you do the work, do what you love, things tend to ultimately work out.
  11. Have a sense of occasion. Life’s short. Celebrate the little things.
  12. Sleep. Be as consistent as you can. Research says get 7-8 hours of sleep per night. That seems to be good for me. Your brain and body do not work well without good sleep. Occasionally I take a nap—because a good nap is second only to sex in terms of pure blissful enjoyment.
  13. Daily exercise. The benefits are endless. Self-esteem, health, sleep, sex, brain function—all improved by daily exercise. So why don’t you have time again?
  14. Wait a day to respond to stuff that bugs you. See if you feel same the next day. Usually not.
  15. Send with love. Send emails with love—seriously. No different than any other intention you have—send messages and emails with love.
  16. Have High-value friends. That doesn’t mean friends that are worth a lot of money. It means friends that support and enrich your life. You are the people you hang out with. Don’t let ‘em bring you down!
  17. Lists save my life. For me, something becomes more real when I write it down. So write it down and work the list.
  18. Can you feel it? FEEL through those life choices DON’T just THINK them through. I know when something doesn’t feel right it usually ends up being a bag of shit I have to deal with.
  19. News & social media. If you need or love to be on it, that’s okay. But otherwise, limit your time. How much good can come from reading negative headlines or tempting yourself with envious Insta-perfect lives?
  20. Read paperback books. Just like you take time to warm up for a workout, you need time to unwind before sleep. That means less blue light (aka your computer/phone screen). So get a good old-fashioned book and read it before bed.
  21. It’s all just a challenge. A spiritual warrior sees everything as a challenge. If it’s a challenge, that’s better than it just being something you don’t like and get frustrated with.
  22. Think before you speak. Is it kind? Is it true? Is it necessary? No? Then keep it to yourself.
  23. Love yourself. It’s hard to love yourself when you don’t love other people.
  24. Be vulnerable. You ain’t perfect. There, now you don’t have to be. Vulnerability cracks open the door for self-love and acceptance.
  25. Take ownership. Taking ownership is a powerful habit. When you take ownership, you no longer give yourself the opportunity to blame or make excuses. Pick a project you can take ownership of and see it through for better or worse.
  26. Re-wild. Nature is a healer. Get out there and be healed—weekly if you can and yearly for some extended unplugged remoteness.
  27. Show up on time. When it’s someone else’s time you’ve asked for, you should respect it. Call if you’re going to be late and apologize for keeping them waiting. You don’t have to offer excuses.
  28. Follow peace and passion. You’ll be happier following peace and passion than you would be if you follow bags of money—that much I know.
  29. Talk to people you trust about your bad mental habits. There isn’t a rulebook for being human. It’s hard to know if you’re doing “okay” so check in with your friends. Share. Be vulnerable and you’ll feel a whole lot better.

Thanks for Reading, be well!

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