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10 Lessons From 10 Years In Business

10 years ago, I started out as a social media consultant and today I primarily focus on helping entrepreneurs build an unstoppable mindset and create a smart strategy.

What’s interesting about reflecting on the last decade is that felt like it took forever in one breathe and like it went in the blink of an eye in another.

Over the last decade...

  • I’ve worked with thousands of entrepreneurs through private coaching, group programs, products and programs, challenges, webinars and more.
  • I've traveled as a digital nomad to South America, Australia, Canada & California
  • I’ve made great decisions and some bad ones.
  • I’ve made money and lost it.
  • I’ve launched programs with success and failed at others. 
  • I’ve had blogs that I thought were stellar, only to get crickets. I’ve had other posts that took off with great surprise! 
  • I’ve gone from being unknown with no experience to winning Toronto’s Best Life Coach as voted by Toronto Star Readers in late 2019 with a decade of experience now.

It’s been quite the ride and in some ways I feel like things are just starting to heat up! 

Overall, I wanted to share with you what I’ve learned over the last decade of building my business and helping may others build theirs.

This list is in no particular order. They all matter and are important to building a successful business from what I’ve personally learned.

I hope that it serves you!

10 Lessons From 10 Years In Business With Jennifer Trask

  1. Take 100% Responsibility for Yourself and Your Success. 

If you want to become successful in business you’ve got to get this one. When you no longer allow outside factors or people to be ’the reason’ you’re not getting ahead...including but not limited to… 

  • not enough time
  • not enough money
  • difficult partner
  • the government
  • taxes
  • the economy
  • the weather
  • the past launch that failed
  • technology 


then you are home free. 

People have built amazing companies amidst financial and economic difficulties. If you want to create something amazing, you’ve got to understand that you are the creator of your reality and that you can make things happen no matter what else is happening. 

When you get this, it’s so freeing and empowering and gives you all the leverage you need. 


  1. Take Care Of Your Health


Eat well.


Be with friends and family. 


Don’t let growing your business damage your health or your relationships. While there are ebbs and flows of busy times, you must prioritize your health because without it you can’t get very far. 

We also know from high performance research that you’ll get more done, be more creative and enjoy the process more when you are in good health and get into flow (versus constant hustling). 

While you do need to be consistent and get work done, never do it at the expense of your health or your relationships. 

Burn out is real and it is preventable.

People are not replaceable. Love them and find a balance with them between building your business and your relationship.


  1. Master Your Mindset & Your Emotions

You hear mindset being thrown around a lot but few people really know what it means. 

When I think of mindset I think about… -

  • your confidence level & courage (ex: can you take risks, put yourself out there and have difficult conversations?)
  • your ability to pick yourself up after you fail (resiliency)
  • your ability to read other people and respond vs react
  • your ability to emotionally detach and make clear decisions
  • knowing when to speak and when not to
  • your ability to feel how you want to feel no matter the circumstances 
  • your ability to create and maintain boundaries
  • your ability to apologize quickly and take responsibility 

Your mindset is the most foundational skill for you to put into place because building a business is sometimes really hard. 

The points I listed above are easier said than done. They take practice, digging into your beliefs, questioning yourself and the world, going against the grain and ultimately choosing to become who you want to become. 

If you want to master your business, master your emotions. 

Because your emotions dictate how you experience your life. 

They also create your attraction factor... 

You don’t get what you want, you get what you are. 

When you feel successful and awesome, you attract more of it. 

When you feel worried, in lack or in doubt, you attract more of that and you take less risks and hide. 

Become obsessed with self awareness, mastering your emotions and understanding people. It will be the gift that keeps on giving in your life and business. 


  1. Know Your Money

This lesson I learned the hard way. For years I would only look at my bank account when I absolutely had to. As you can imagine, it didn’t go so well. 

Make friends with money. Understand how it works. Know your numbers. Understand where your revenue comes from, what your expenses are, save for your taxes and don’t be afraid to get help, ask questions and learn it inside out. 

Money is energy and it’s not to be feared. 

Money is a tool to help you have a great life and bless others. 

Money isn’t scary, it’s not understanding it and therefore making consistent bad decisions around it that is. 


  1. Get An Entrepreneurial Community

Find friends and colleagues who are all moving in the same direction. Fill your cup up with other entrepreneurs who are doing the work, inspired by challenges and wanting to make a difference with their business and who want to be the best versions of themselves. 

There’s a saying that you are the average of the 5 people you hang around with the most. 

This is absolutely true. 

When you are around inspired go-getters it gives you that extra ‘oomph’ to do it, too.  

Join a co-working space, a membership site, mastermind and go to entrepreneurial events. Find your people, build relationships with them and help each other grow. Some of my absolutely best friends are entrepreneurs whom I have grown with. 


  1. Accountability

Studies show that you are 95% more likely to get what you need done if you are accountable to someone and have a weekly meetings. 

Give yourself the gift of accountability. It will help you do things you don’t want to do but you need to do. It will push you and help you grow. 

You can find accountability in many different places, a coach, mentor or accountability buddy from a course or group you are in. Get one who holds you accountable and to whom you WANT to be accountable to.

Many of my clients have said that they got more done from working together simply by virtue of not wanting to show up to our weekly meetings without things done. 


  1. Master Your Ability To Focus 

There are three areas of focus that matter to your success. 


Area 1 - Stay consistent with your marketing strategy

We’ve all been there. You’re doing your blog, networking and finally getting consistent with your Facebook marketing and then you hear about the latest and greatest social media site OR you decide it’s time to tackle funnels, webinars or maybe start a membership site. 

Shiny object syndrome and FOMO are real, especially in this day and age of social media. 

BUT you must be disciplined and stay focused with your strategy. 

Most entrepreneurs are not giving their marketing strategies enough time to work well. They are doing things for a few months and then on to the next thing. 

If you’ve done that, that is why your marketing is not working. 

You’ve got to get clear on what the best strategies are for you to reach your audience and then stick to them. Once you master something you can move on, but until you are getting epic results from your marketing, don’t be swayed, stay focused! 


Area 2 - Stop Working With Distractions

From pings and dings to texts and emails to DM’s, messenger and newsfeeds. Distractions are everywhere and they killing your progress. 

Studies show that when you keep switching tasks (which happens when you get distracted by a text, phone call, email ping, social ping, etc.) you can lose anywhere from 12 -20 minutes of time! 

Not to mention that your best work comes from regular focused times on work. 

Think about the last time you were so immersed in something that you got lost in it. I bet you had some great ideas, did your best writing or gave your best talk. 

Getting rid of distractions is paramount to you honing your skills and to you being able to get things done. 


Area 3 - Do Your Most Important Work First

This idea is not new but I’ve noticed, even with myself, that often times we avoid the work that will really move us forward. This is because it’s usually harder than other tasks (either in doing the task or the results that will come from it, like being seen).

It breaks us out of our comfort zone and it forces us to get into focused work (not the distraction-happy, dopamine-filled world we are used to living in). 

A strategy I’ve used to help me conquer this is telling someone (or publicly announcing it on social media), that I am doing this thing and I want to be held accountable. I’ve also done the work while working with my accountability partner. Whatever you need, make it happen because you want to focus on the work that will move your business forward the fastest, even if it’s hard. 


  1. Success Takes Time

Over the last decade in the coaching industry I saw something interesting happen. There was about a two-year period where this wave of ‘coaches who coach coaches’ came and made some BIG promises from a results perspective. It seemed like everyone was an ‘overnight sensation’.

During that time I spoke with a lot of coaches who invested a lot of money in “business” coaches who had little to no experience and couldn’t fulfill their BIG promises of 6-figure pay days. 

Here’s the thing: success takes time. 

It’s not sexy.
No one wants to hear it.
But it’s the truth. 

And that’s why you can’t be in business for the money, fame or outward success. 

You’ve got to be in it because you’re so passionate about it that there’s nothing else you’d rather be doing. 

When you start and lead from there, you’ll make it. 

I’ve talked to a countless number of entrepreneurs who were making their journey harder because they felt bad about their progress simply because they have unrealistic expectations about what it really takes. 

Talk to any seasoned entrepreneur and they will all tell you the same thing: this a marathon, not a sprint.

Be patient and keep making progress. If you do that you’ll get there eventually! 

Please don’t judge your timelines against someone else’s. There are SO MANY FACTORS that determine one’s ability to succeed in business that you just can’t pin yourself against someone else’s journey.

Your journey is uniquely yours and that’s how it is suppose to be. Honour It. Love it and be present with it. 


  1. Get Mentors, Coaches & Learn From The Best

You’ve likely heard this one before yet so many entrepreneurs are afraid of investing in themselves and/or in their businesses. 

The fastest path to what you want is to learn from someone who has paved the way to shorten your learning curve. 

  • Read books
  • Take courses
  • Hire coaches
  • Get mentors
  • Go to seminars and workshops and
  • Do the work. 

Don’t try to learn it all yourself. It’s harder and longer alone. 

My only advice when investing (especially in bigger things) is that it should feel right and never do it because you feel pressured or because of FOMO.  

It should be the next logical step for you. 

And of course, be sure to do your due diligence and invest in people who you have a relationship with or have a good track record. If they are newer to business they should be priced accordingly and honest about their knowledge and experience. 


  1. EnJOY The Journey

I did an exercise at a workshop last year about what success really is. 

At first people said, “Money, clients, lifestyle, etc." 

Then I asked them, ‘What does it take to get the money, clients and lifestyle?”

We came up with this list: 

 What Success Really Is With Mindset & Business Coach Jennifer Trask


Money, clients and lifestyle are the RESULT of being successful day in and day out. 

Success is showing up daily and doing the work. It’s things like writing your blog post every week, following up, taking a course, doing the inner work, practicing your speech, creating your course, serving your clients, etc. 

These things are "the process" and when you fall in love with doing those things you’ll love your days. 

And when you love your days you’ll have more joy, creativity and fun. From that space you have access to your best ideas, flow state and manifestations that will blow your mind! 

Leave the outcomes behind and focus on getting better at and enjoying the process. 



So there you have it. 10 lessons from 10 years that I believe will help bring you more joy and fun on your journey - which if it isn’t fun, what’s the point right?! 

Overall, being an entrepreneur has been the hardest yet most rewarding thing I’ve ever done. It’s stretched me beyond my comfort zone,  forced me to become more self aware than I ever realized I could be and I believe has served me to be more kind, compassionate and determined! 

Entrepreneurship is like a roller coaster. Like any great roller coaster it will thrill you, scare you and make you feel more alive than ever before! 

This journey is so worth it. You’ll be proud of who you become. You’ll be proud of what you had to overcome and you’ll LOVE the impact you make, the people you meet and the lifelong friendships you'll create. 

Entrepreneurs are some of the most caring, courageous, creative and all round AMAZING people on the planet!! 

Here’s to being an entrepreneur and making positive change in the world. 

I’d love to hear from you, is there a lesson you’ve learned from entrepreneurship that stands out? Leave a comment and let me know!! 

To the next 10 years, 

Jennifer Trask - First




Ready to change habits that don't serve you as an entrepreneur? Be sure to grab... 

 The Top 10 Sabotaging Habits Of Entrepreneurs (and how to overcome them)
Written by Jennifer Trask at 12:24

User Comments

Jennifer Trask

You're so welcome Lisa!! It certainly is a journey - but totally worth it! :)

Lisa Hall

Thank you Jennifer! Excellent blog to encourage and give honest clarity on what it really takes to be a successful entrepreneur. Much appreciation to you!

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