Meet Jennifer Trask

We caught up with the brilliant and insightful Jennifer Trask a few weeks ago and have shared our conversation below.

Jennifer, so great to be with you and I think a lot of folks are going to benefit from hearing your story and lessons and wisdom. Imposter Syndrome is something that we know how words to describe, but it’s something that has held people back forever and so we’re really interested to hear about your story and how you overcame imposter syndrome.

I wish I could tell you that I heard one sentence that changed everything and all of the sudden I didn’t feel like an imposter anymore but that just wasn’t the case. Looking back, I can narrow it down to a few things that really helped me.

First, is the thing that no one wants to hear but it’s true: time in the trenches. The more clients I worked with and more skills I acquired, the higher my competence and confidence went.

Next, affirming how good I am was a VERY helpful tool. We have 10,000’s of thoughts everyday, most of them negative. Because we become what we believe I knew that the more I told myself I was excellent at what I do, especially after I just had a great call with a client, then the more I would believe it. No one talks to us as much as we do, so talking myself up to myself was essential to speeding up confidence and overcoming imposter syndrome.

I would say things like, ‘You’re such a great Coach. See how you helped her do “insert awesome thing”? That’s because you care and are great at what you do!’

I was and still am my own best cheerleader.

Lastly, as a woman, not seeing many women in power in my industry gave me an unconscious bias that it was harder to reach big heights. But the more I learned more about Patriarchy and the roles that women have in the home, the more I realized it had nothing to do with capability, but access and opportunity.

That understanding helped break down invisible barriers in my own mind. It also made me determined to help more women build successful businesses!

Thanks, so before we move on maybe you can share a bit more about yourself?

I work with female service providers and help them build joyous businesses. We focus on mindset, messaging, marketing and money! What’s special about the way that I approach business is that I focus on helping each woman to find what truly makes her unique and to help her build her business in a way that fits her personality and lifestyle. To help her focus on her strengths and not having her do a bunch of things she doesn’t want to do.

I also love helping my clients feel good about their journey which is why my accelerator is called, The Joyous Journey. Building your business will be hard at times but overall it can be a very joyous process if you have the right mindset and community around you.

My coaching style is empathetic mixed with a ‘tell-it-like-is’ and ‘let’s have fun along the way’ approach. Clients share that they can take a deep breathe with me. That they’re able to feel good about where they are and to embrace their reality in a way that’s empowering.

I’m excited to share that I’ll be launching my brand new podcast – The Joyous Entrepreneur – on March 1, 2025! This would have been my dad’s 77th birthday so it’s a nice way to pay homage to my first entrepreneurial mentor, my dad.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

1 – Grit, which author Angela Duckworth describes as a combination of your passion and perseverance is the number one qualities that comes to mind.

While business is fun and rewarding, it’s also frustrating and exhausting. You REALLY need to want it. That means that you need to be really passionate so that you have the perseverance to stay in the game long enough to find success (and then stay there).

2 – Being visionary is really important. There’s the obvious reason because you need to cast a vision about what’s possible to yourself, your team and clients. But it’s also important for when times get tough. When you’re a visionary you can see the long road and that empowers you to be able to navigate short term setbacks and losses better than someone who has trouble seeing the future they want.

3 – The last quality that’s important for entrepreneurs to develop is open-mindedness. In order to succeed in business you need to be open minded about new opportunities, seeing things differently and receiving feedback without taking it personally. When you’re closed off or you think it should be ‘your way’ you’ll miss opportunities and critical junctures that can lead you down a path you don’t want to be on.

Staying open-minded is important to long term success. Plus, it makes you a better leader and team member.

We’ve all got limited resources, time, energy, focus etc – so if you had to choose between going all in on your strengths or working on areas where you aren’t as strong, what would you choose?

Always focus on your strengths and hire out the rest as fast as possible. In the earlier years of business you often do need to do a lot of things because you don’t have the money to hire everything out. But as you make more money, hire things out so that you can free up your time to work in your zone of genius. The more you can do that, the faster you’ll succeed.

The only skill that I do encourage every entrepreneur to sharpen, even if you want to hire it out later is copywriting. Copywriting for sales is a skill that spills out into everything from emails you send, posts you make, sales page, your website, conversations, etc.

Even if you do hire it out one day, you’ll be able to give great feedback and help your brand grow faster the better you are at writing copy.

Contact Info:

Image Credits

Mike Day, The Art of Business Photography.

Suggest a Story: BoldJourney is built on recommendations from the community; it’s how we uncover hidden gems,
so if you or someone you know deserves recognition please let us know here.
What would your closest friends say really matters to you?

If you asked your best friends what really drives you—what they think matters most in

When do you feel most at peace?

In a culture that often celebrates hustle and noise, peace can feel rare. Yet, peace

When did you stop hiding your pain and start using it as power?

Almost everything is multisided – including the occurrences that give us pain. So, we asked