10 Daily Habits of the Most Successful Entrepreneurs

Every day I struggle with these points. Entrepreneurship is hard. It requires consistent discipline, and confidence in yourself. Lots of people won’t enjoy it. But for those determined few who can find a way to make the grind work, entrepreneurship is the most rewarding job, lifestyle, and identity in the world.

“Either you run the day, or the day runs you.” –Jim Rohns

This article is to give any aspiring entrepreneur a head-start on building those crucial habits all entrepreneurs need, or help reaffirm them for existing entrepreneurs.

The 10 Daily Habits

1. Create a Routine

Every morning and night I do the same thing. Wake up, wash face/brush teeth, meditate (best when you’re still a bit dreamy), bodyweight exercise, eat my breakfast burrito from Sunday’s meal prep. Every evening I have a separate routine involving hygiene, journalling, and preparing for tomorrow.

This helps keep me grounded and consistent.

The best entrepreneurs build daily, weekly and monthly routines like mine grounded in keeping themselves sane, productive and happy. Entrepreneurship is stressful and you’ll find stable routines become your bedrock on which you structure your life.

2. Start with the days hardest task

Known as “Eating the Frog”, this means when you’re freshest early in the day start with your most frustrating, grueling or procrastination inducing task.

This has a range of benefits.

  • It makes every other task seem easier by comparison.
  • It immediately gives you the dopamine rush of accomplishing something worthwhile.
  • It prevents you from procrastinating on important tasks for too long.

I’m happy your reading this article, but the second you’ve finished reading go eat the frog. The rest of your day will seem like a breeze by comparison.

3. Workout and Meditate

I struggle with this one myself. Routines are easy to follow when life is easy. But the second I’m travelling, or anxious or stress out about something, or I’m just busy. I ditch my morning routine to try and create time or space for myself, sometimes entirely by accident.

Which as I’m sure you’ve guessed just makes things worse. I become irritable, feel sluggish, my minds foggier and I end up being less productive overall even with the “extra” time.

Don’t make excuses. Fitness and mental calm are crucial for a happy lifestyle. They’re the building blocks of productivity not just for days, weeks or months. But years and decades. I want to be a vibrant member of my community well into my old age, and putting in that little bit of effort daily towards your health is how you get there. Find some activity, sport, or practice that works for you and make it habitual by keeping yourself accountable.

Man Exercising

4. Plan tomorrow, today

As part of my night routine, I make a list of my tasks for tomorrow, and plan how different meetings, appointments and so on will all be chained together. This lets me pack my bag, thaw my meal prep and overall get ready for tomorrow when I’m awake and alert. So when I wake up and I’m groggy and tired I don’t have to worry about it.

Give this a shot tonight, you’ll find it takes way less time than you thought. That it gives you some understanding about tomorrow you didn’t have before (including what your frog to eat is), and it helps you catch things you may have missed (meetings you forgot about etc.)

5. Align Yourself with Your Priorities

The common way of doing this is goal-setting. I keep an Excel spreadsheet with short, medium and long term goals and frequently refer to it to keep the bigger picture of my work in focus. Some people find having time frames like 1, 3 and 5 years helpful but I find it makes it easier to procrastinate on the later ones. The trick with this system is to continually pull goals forward as the situation in your life changes.

For instance I’ve always wanted to complete an Iron Man Triathlon but it’s always been a 3+ year goal for me. But I identified that I had a block of time where I could work on something like that. I looked into my longer term goals, thought through different scenarios, figured the Iron Man would fit nicely into this block and have now been training for several months in preparation. I just finished the Toronto Marathon as part of my work-up training. That’s the power of these goal setting systems. They give you space for what matters.

Tower With Cables Coming From It

6. Keep Track of Your Progress

I find the best way is to keep a daily journal. I still haven’t nailed down my system yet. I prefer writing by hand, but then I find I fill up notebooks that I can’t organize, refer back to or really read ever again owing to my messy handwriting. While I prefer a digital journal I find typing up my thoughts much less relaxing than writing them free-hand. I also find that because I can type much faster what I write tends to be more shallow because I don’t need to think it through as much as when I’m writing by hand.

Find some system for yourself that works. Keeping track of your days, weeks, months, thoughts, ideas, dreams and perceptions is crucial to staying grounded in your own life. I find I’m much less compassionate, outgoing and empathetic when I don’t make the time to understand my experiences. If you’ve never kept a journal before, please try it. You’ll quickly find it’s a very enjoyable way to end your day, and the benefits ripple throughout your entire life, both professionally and personally.

7. Make Time For Your Community

Each of us has our own distinct communities. For me it’s my family, a few high school friends, a couple University friends, and some people I’ve met at various competitions and events who I keep in touch with through FaceBook Messenger. For you it might be a sports club, your children, your spouse or significant other, co-workers, or anyone else you find you enjoy spending time with socially and who enriches your life. We each have our community. But it’s both a responsibility to them as well as to ourselves to make sure we stay connected to them on an ongoing basis.

I find in my life, if I get busy and stop seeing my friends, and stop being present emotionally and intellectually with my family, I’m far more prone to becoming detached, burnt out, or irritable. These people we each cherish are so essential to our happiness, it’s a shame how easy it is to stop giving them the time they deserve.

Make sure you recognize your who your community is, and make it a priority to be engaged, empathetic and present with each of them at least once a week (varies obviously depending on if it’s your kids, spouse or some co-workers you get drinks with).

Group Of People at Dusk

8. Encourage Your Team

No matter what sort of entrepreneur you are you have some sort of team backing up your success. If you’re like me I have partners I’m working with on various projects, co-workers and team mates at University. I also have people who read my writing, and these are my community and team members who I cherish and try and encourage in their own lives. Maybe for you, it’s your team in a management role, or your co-workers in some department. It can even be your boss. It doesn’t matter. Your team is whoever you’re directly connected to in your professional life who you in some way rely on.

Make time to encourage these people, do check-ins and make sure they’re aligned with their goals. Ensure they’re developing both personally and professionally. If their family or home life is out of sync it’ll effect their performance. Ask questions and deep dive into what they dream about in their hearts. This stuff matters and the leaders who make an impact, the Level 5 Leaders who change the world know that they are their team, and can only succeed if their team does.

9. Prioritize Deep Work

This is a concept from Cal Newport that I love. It mirrors Csikszentmihalyi’s concept of Flow. But instead it’s something we’re agents of instead of something that sort of happens if we set the variables right.

The most impactful entrepreneurs find time each day for working deeply on their most important objectives. Deep work is the product of your time spent working on the most important hurdles towards achieving your goals, multiplied by the depth of focus you can bring to working on it.

*High-Quality Work Produced = (Time Spent) x (Intensity of Focus)*

Knowing what that task is, comes from point 2 and eating the frog. But being able to bring your deepest level of focus to the task is another skill entirely. It requires a careful cultivation of your workspace to eliminate distracting colours, objects, and sensory stimulus. It requires ignoring email, social media, and shallow work like ordering that thing you definitely need now on Amazon. Those small tasks should be on the periphery of your working day, done once your willpower is used up and you’re tired and have accomplished what you needed to.

I usually schedule two blocks for deep work each day, with carefully planned outcomes and I do my periphery work like email in the evening once I’m mentally drained and ready to relax. Try and track how much time you spend actually working deeply and if you’re surprised at the number, take action to change it for the better. You’ll find a level of productivity you didn’t realize you were capable of.

Man Working Near Chalkboard

10. Schedule Some Learning Daily

Entrepreneurs need to continuously learn. The world is constantly changing, and the most impactful entrepreneurs develop their “T-Shaped Profile” by constantly engaging with knowledge corridors at the periphery of their expertise.

My background is in design and strategy but I find as an entrepreneur I’m consistently required to know some engineering and computer science to contribute more meaningfully to my ventures. I’m not particularly skilled at either. But every day I make time for learning about them through reading books, doing exercises, and listening to podcasts. Through that small investment of time daily my skills and understanding have advanced miles in the past few months.

Look into your future goals and identify what skills or capabilities may eventually be roadblocks for you and start learning today to be ready for those challenges. For many engineers and designers that roadblock may be management, project planning or finance. What yours are may surprise you.

No matter what you feel is most important, everyone has some subject they could stand to learn more about, and more understanding about the world is always going to be a competitive advantage for you. Think of it as a small investment today that pays dividends for the rest of your life.

Learn as if you were to live forever. –Mahatma Gandhi

You may have noticed a trend in these entrepreneurship skills. None of them are really about business. The most successful entrepreneurs aren’t the slickest financiers or most charismatic public speakers. They’re the ones who can commit to realizing change in the world, and weather the marathon that it takes to see that change through.

It’s never easy, often frustrating and unusually fun.

It requires you to structure your entire life around that mission to ensure you don’t burn out or abandon the rest of your life, and that you remain consistently, vibrantly happy.

In the end, the only real success is personal success.

Now go out there and change the world.

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Andrew is a design graduate student in Toronto who writes about leadership, design, and startups. Visit his blog Lead Boldly for exclusive content. Or say hey on Quora | Instagram | FaceBook | Twitter | LinkedIn.


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