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10 Questions with Coaching Expert Jennifer Trask

When Jennifer Trask took her first step down the coaching path, she had five goals in mind: to be her own boss, to be 100% digital, to serve millions, to earn unlimited income, and to love what she did.

Fast forward to today and she has achieved them all. But how?

As we all know, most coaches and consultants share those same dreams, but only a fraction reach them. Jennifer, through her determination, effort, insight, and truly compelling personality has worked her way into that fraction, and in today’s featured profile, she shares a bit of her secrets below.

SH: To get started, tell us a little about your background.
I grew up in the beautiful town of Corner Brook, Newfoundland, Canada. It was a wonderful community to grow up in. I remember being on skies when I was 5 years old! I have three siblings, two of which are also entrepreneurs and one who is marketing. They have blessed me with six incredible nieces and nephews!

I have a Bachelor of Commerce in Marketing and a MBA in International Business. I’ve traveled to 27 countries and lived extensively in eight of them! For me, traveling is one of my best teachers (as is growing a business)!

Toronto, Canada is now home.

SH: How and why did you get started in coaching?
I started coaching by accident. I was a marketing consultant and I noticed that a lot of my clients weren’t taking the action they said they would. In wanting them to succeed I started using the coaching tools that I had learned over my years of building my business and it worked! People starting taking more action and getting more results. The rest as they say, is history!

Video Spotlight

with Jennifer Trask

SH: What did you do early on in your coaching career to set yourself apart?
There are three I did that I believe set me apart from others.
1. I niched myself and I was in 100% alignment with that decision. Deciding to coach only coaches is when my business really took off. I had found my ‘home’ and felt confident that I could do it.

2. I was consistent in my marketing. This is where most coaches fall down but I didn’t. I stayed focused and consistent and it worked.

3. I was myself. In the past I had put on more of a persona of what I thought people wanted me to be in order to take me seriously. Not this time. I even created pink and purple branding because they were and still are, my favourite colours! They make me so happy! In the past I used colours that I thought were more professional. Giving myself permission to truly be myself gave me confidence and clarity like I hadn’t had before.

I was myself. In the past I had put on more of a persona of what I thought people wanted me to be in order to take me seriously. Not this time.

SH: If you could only use one method to get in front of potential clients, which would you choose?
Speaking (online or offline). For me, when people hear me do a talk or a presentation (whether it is virtual or in person) they really connect with me. I’ve always been comfortable speaking and on top of that it is without a doubt one of the most powerful marketing platforms out there.

SH: If you could only use one method to enroll those potential clients, which would you choose?
After a presentation, I would sell deep dive coaching sessions (mine are 2 hours). They really help the client gain a lot of clarity and progress and it also allows them to see what it would be like to work together and what we could accomplish together in a longer commitment. It’s a powerful selling tool to someone who is a serious prospect because they have paid to be on that call. It’s important to price those calls so that only those who are serious will invest in them.

SH: Which business decision allowed you to grow your practice more than any other?
To focus on coaching coaches. When I allowed myself the opportunity to focus on just getting to know one industry really well – the one that I adored the most – it just worked. You can’t be all things to all people. My dad was a very successful entrepreneur and he would always say to me, ‘Focus, Jennifer, focus!’ Haha… thanks dad! 😉

When I allowed myself the opportunity to focus on just getting to know one industry really well – the one that I adored the most – it just worked.

SH: If you could go back in time, what advice would you give your younger self?
Learn how to manage your money exceptionally well. This includes taking taxes out immediately, prioritizing paying down debt and spending within your means.

SH: What mistake do you see most new coaches make? And can they avoid it?
There are two big mistakes most coaches are making and yes, they are avoidable.

Mistake #1. They don’t prioritize their mindset.

The most important thing I’ve learned about growing a business is that it takes a huge amount of emotional energy. It also requires you to see yourself in a different light and step in to a new identity.

Growing a business brings many challenges that likely that new coach hasn’t experienced before. As a business owner you are essentially a problem solver. For your customers and your business. You must be able to deal with challenges well and learn how to not take them personally, especially ones about money.

You can avoid this by prioritizing your mindset work everyday and learning from someone who specializes in this area. You do become who you hang around with regularly so be sure that you are reading books, listening to podcasts, joining courses and classes, masterminds and/or hiring a coach, who has the mindset you want. Being in the environment of where you are going will get you there faster. Master your mind and you will master your results.

Mistake #2. They underestimate the amount of time and learning it really takes to build a sustainable business.

When you are building a coaching business it’s important to understand that you are trying to master two major skills at once. The skill of being a great coach in your niche (your craft) and the skill of being a successful entrepreneur (the vehicle to practice your craft).

These are two separate skills.

As one can imagine, learning how to grow and run a profitable business is no small feat. Most coaches underestimate the time and think it will happen overnight or even within a year or two. This has become highly prolific recently due to the overnight sensationalism marketing that is going out to coaches in the last few years on social media promising big pay days in small periods of time. This is highly damaging to our industry for so many reasons – too many to name here, but in relation to this question, it gives people unrealistic expectations.

When people don’t make $X in Y time they think something is wrong with them. They believe that they aren’t ‘cut out’ for this and/or a host of other negative thoughts. This is making a lot of coaches quit or shrink before they should.

Having been an entrepreneur for a decade now, I can tell you that strong, profitable and sustainable businesses are not built in a year. They take much longer.

The good news is that you get to earn while you learn and with the right mindset you will enjoy the process of building your business. It’s important to understand that there are too many factors that will determine your ability to succeed in business for anyone to make financial pay day promises to you.

And for those who are curious, the #1 factor that will determine your ability to succeed is your mindset. It is your greatest asset and you must learn how to use it to your advantage. The rest falls into place when you have a strong, success minded mindset.

SH: Imagine waking up tomorrow and it’s all gone. What are the first three things you’d do to rebuild your coaching practice?
1. Network, network, network.

2. Start speaking (online and offline).

3. Create as much valuable content as I could and get it out there.

SH: What is your best advice for a coach just starting out?
Find a mentor or coach who has walked your path and hire them. Whether it’s 1-on-1, in a group, mastermind, etc. The fastest path to what you want is to find someone who has done it and learn from them. It will save you years of time and you will earn faster and therefore have a larger impact. Trying to do everything alone is the hard way. Don’t be afraid to invest in your business.

Our line of work is one of the lowest investment businesses you can get in. You can start with virtually nothing. Those who invest smart with mentors who can help them learn what they need to learn faster will get ahead of their peers who try to do it alone. Be sure to do your research and invest with mentors who you really align with and believe in.

Oh and I can’t forget this important nugget of wisdom: go at your own pace. Give yourself permission to be where you are and grow how you need to grow. Forget what others are doing or their timelines, focus on your own game and don’t compare yourself. You WILL get there if you stay on course, no matter the timeline. You are the only person who can do the work you came to do, don’t give up on yourself. Your future clients will thank you and so will you. 🙂

Give yourself permission to be where you are and grow how you need to grow.

SH: What are you working on right now?
Many exciting things!! Right now, I am working on shifting my branding to mindset for entrepreneurs because it really is the #1 most important key to success. I do still however, work privately with coaches on growing their businesses through strategy and mindset.

I am also working on doing more in person speaking and small group events (as well as some small online groups and masterminds). I love when small groups come together. It’s so powerful and creates an intimate atmosphere that everyone benefits from.


Jennifer Trask


Bachelor of Commerce, MBA


Business Mindset


Win Win Sales Conversations


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