The Best and Worst Habits of Highly Effective Entrepreneurs

The Chic Geek
The Chic Geek
Published in
7 min readAug 31, 2017

Tina Poon

In the beat of a heart and the flash of a gun, Usain Bolt cemented his legacy by setting a World Record in the 100m sprint and becoming the Fastest Man in the World. We define Bolt by the flashy medals and the lustrous highlights, but what we often forget are the everyday habits that fill the in-between moments: the strict dietary routines, training sequences, and pre-race rituals that make a champion. While not everyone will win an Olympic Medal, the everyman victory still results from everyday habits that over time lead to a promotion, a raise, a rewarding career, etc. I decided to ask seven real-life entrepreneurs what they believe are were the best habits and tips that led them to their success, as well as the bad habits they had to rise above to get there.

Kylie Woods | Founder & Executive Director of Chic Geek

Chic Geek

What is your best tip when it comes to being a highly effective entrepreneur?

Put first things first.

That’s Habit 3 in Steven Covey’s The 7 Habits of Highly Effective People. And it’s one that I struggle with every day. For me, it means looking at all the tasks on my list more strategically; picking out the big, important things and tackling them first. Otherwise, it’s easy to get caught up doing a bunch of little tasks that really didn’t impact much.

When I prioritize the important things and make sure to work on them first (whether that’s carving out 4-hours of quiet time or tackling them as soon as I wake up) it makes me a more effective entrepreneur.

What’s the habit that you have to constantly work to overcome in order to experience success?

My worst habit is that I’m a closet procrastinator.

Instead of tackling these big rocks straight on, I’ll avoid them like the plague and do everything else (from cleaning my kitchen to the bathroom toilets or pluck through my inbox on a mission). It means that at the end of the day, I might feel like I’ve gotten a lot of things done, but I still carry a certain level of anxiety because I didn’t do the one big thing I knew I needed to.

Crystal Phillips | Co-Founder & Executive Director

Branch Out Neurological Foundation (branchoutfoundation.com)

What is your best tip for those who want to be a highly effective entrepreneur?

Outsource your life! No need do/be everything. Identify where you’re an expert and outsource the rest. I used to think it was lazy; now I believe it is most efficient and effective.

What is the habit that sabotages you? Do you have a solution?

I used to repeat to others or in my head that “I’m stressed” and “I’m too busy”. I made it my new year’s resolution a few years ago to never refer to myself as being stressed or busy and, WOW, what a game changer. I started to feel less stressed and busy even though my schedule didn’t change. All that time stressing about being stressed and busy could now be spent on focusing on what I needed to accomplish in that moment/day/month. Try it even for a day; it might surprise you!

Chris Hammer | Psychologist & Certified Life Coach

Silverhammer Coaching Services

What is your best tip for being a highly effective entrepreneur?

I believe you have to stay knowledgeable and current to be effective in any endeavor, but that success is the result when hard work and preparation meet luck and opportunity. You never know an opportunity will present itself, so a person just needs to keep trying despite feelings of discouragement and streaks of bad luck. So in short, I think the answer to this is perseverance. As Thomas Edison once said, “ Many of life’s failures are people who did not realize how close they were to success when they gave up”.

What is your worst habit? Do you have a solution?

My worst habit is procrastination. The solution I try to stick to is to remember that “action precedes motivation”. I just get to it, whether I want to or not, and take a small action. More often than not, motivation follows and the small action I committed to originally takes on a life of its own and becomes a more significant action.

Alex Putici | Founder & Serial Entrepreneur

Work Nicer (http://worknicer.ca)

What is your best tip for being a highly effective entrepreneur?

Trust the process. Understand that balance isn’t a constant state. If things are good right now, chances are they aren’t going to stay that way. If things suck right now, they probably aren’t going to stay that way either.

Be honest with yourself. The least effective entrepreneurs probably shouldn’t be entrepreneurs in the first place, and that’s okay. Entrepreneurship is a skill like any other. You can get better at it with practice, but that doesn’t mean you’ll necessarily have the ability to see success in it. Don’t get into this thing if you aren’t sure it’s for you. Entrepreneurs need people with entrepreneurial tendencies around them to build great things.

What is the habit that sabotages you?

Distractions/lack of focus. I’ve tried everything under the sun to find a solution. When I was a kid I was on Ritalin; that apparently worked then. But, for now, the best thing has been to build a team around me that relies on me. If I can’t stay focused or get things done just for myself, I will for sure get it done for my team. They also know I struggle with this and are the first to tell me to get it together when need be.

Kadie Hummel | Principal Photographer

Kadie Hummel Photography

What’s a habit you have that helps make you an effective entrepreneur?

My biggest tip is to wake up early and set your intentions and goals for your day. My brain is most productive and full of ideas in the morning, so I use that time to hash out to-do lists and jot down thoughts, ideas or resources I come across that will benefit my business. If you find a system that works for you, it will become habit, and your workflow will be a lot smoother.

What bad habit do you have to constantly work to overcome?

I am extremely critical of my own work, and can be super hard on myself, which I think is totally normal for any business owner / artist / entrepreneur. It’s important to want to learn and improve, but it’s also important to be aware that you’re your toughest critic Asking for opinions from a mentor or close friends helps me learn, but also quiets any negative thoughts and turns them into constructive ideas.

Lynnell Ible | Leadership Coach, Trainer & Leader

Better Leader Better Life

What is the best tip you can offer anyone who wants to be a highly effective entrepreneur?
Learn to make mistakes, you will at least once. You will make a bad financial decision, you will lose a client, you will lose a deal. Someone will refuse to pay your invoice. You will have clients you will need to fire. You will make a decision only to find out it was the wrong one.

Success is not because you are the most talented, the most gifted or the “expert” in your given field. It is because of the risks you take where you fall flat on your face and your willingness to pick yourself up and learn from them.

What’s the habit that sometimes stands in your way?

Doubting my capabilities to succeed. Entrepreneurship is hard and, when I have fallen on my face, sometimes I feel like it would be easier to get a job. To give the responsibility of my pay check to someone else.

I remind myself that success is because of failures. Getting myself out of a fixed mindset (my success is based on my current abilities) into a growth mindset (my success is based on my effort) is key.

Micki Mutch | Founder

The Olfactory Shop

What is your best tip for being a highly effective entrepreneur?

Plan! A new, but highly effective habit that I wish I had from the beginning, is to plan with the end in mind. It doesn’t mean this will absolutely be the outcome, but it’s saved me from my bad habit of shooting on a whim and hoping I have something to land on. If you can see the goal, you can plan for it! You don’t need to wait for action until every step of the plan is in place, but knowing what you want, and which path you want to take, will help you get off to a strong start.

What’s your worst habit, and how do you overcome it?

Not planning. Acting on impulse without being thoughtful. My solution is to give myself time each week to think through what actions are needed to achieve my goals. I place my big goals in my weekly planner so that I don’t forget how each task is a step towards them.

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The Chic Geek
The Chic Geek

is a Calgary-based non-profit building a supportive community for women at the intersection of technology and entrepreneurship. http://www.thechicgeek.ca