Theresa Cantley Entrepreneur Strategist

My Top 5 Lessons I’ve Learned Being An Entrepreneur

There are a few common misconceptions I’ve heard about being an entrepreneur….  “Oh, you get to work in your pajamas, you get to stay at home and drink coffee, and you can just hang out!

Ahem…  You and I know better.

As an entrepreneur, you work your butt off.

You work long hours. You work anywhere.

You face fear every day, many times every moment of every day. You love your work.

You doubt yourself. You celebrate your big wins. You celebrate your small wins.

You compare yourself to other people on social media. You love yourself, the whole you.

You have freedom of time, you have peace of mind, you love what you do and you do what you love.  This is what I’ve learned over the years being an Entrepreneur…


My Top 5 Lessons I’ve Learned As An Entrepreneur…and Some Input From My Awesome Clients  


Being an entrepreneur certainly has its ups and downs. You may ask yourself, “Am I good enough? Am I reaching people? Do I need to change anything?”  The words “pivot” and “consistent” become permanently part of your vocabulary and the phrase “digging deep” doesn’t refer to holes in the ground for plants.   

All of these struggles we go through, they are all part of the entrepreneur’s journey. Without the struggle, we would NOT be who we are today. If you think becoming a successful entrepreneur is matter of luck, think again. If you think it’s a matter of the other person being smarter, or having more degrees than you, it’s not. What it comes down to is, a matter of mindset, a matter of strategy, AND a matter of having that grit to keep going. That motivation to get up every day, to show up every day, no matter what. It is everything. 

If some days, you think to yourself, “What the heck am I doing?” you’re not alone, believe me. I’ve been working with Entrepreneurs for quite some time and I thought to help us all with these periods of doubt I decided to compile the “Top 5 Lessons I’ve Learned Being an Entrepreneur.” These five things are based on their feedback (and some of my own) that may help you to shift your mindset when you find yourself in a swirl.  I’m confident that these five things will help you to shift your mindset and to keep going, to keep believing in what you’re doing.

Lesson #1:  Believe in your own abilities. Most importantly, believe in your ability to figure things out! 

We’ve all had struggles and challenges that we’ve been through. Remember that incredibly difficult project you had a few years back? The one you were able to tackle with grit and grace?  A lot of times we forget. In the face of the next challenge, we forget just how we got through those challenging times.  It’s a human tendency to forget all of the little successes we’ve achieved.  To think that somehow, we aren’t enough.  But stop and think about it. When you look back at one of these successes, you’ll be saying, “Oh my gosh, I was able to do it! I was able to figure things out, I was able to look at the problem and get through it!” Whether it was trying to do something technical like recording a live video, or maybe something as simple as getting through a difficult conversation with a customer. The bottom line is, you have to believe in your ability to figure things out. When you believe that wholeheartedly in your gut, that you can do it, you can get through anything. But you need to know and believe it, deep down in your gut, that you are enough. I say to myself daily, “In my gut I know that I was born to do this, I was born to be an entrepreneur.” You have to believe it in your heart and soul, beyond anything else.

Lesson #2:  Find a mentor who has already achieved what you want to achieve. 

Find someone out there who is inspiring to you, find someone out there who has already achieved what you want to achieve, and learn from him or her.  My first mentor was Marie Forleo, and she helped me change my mindset from being a corporate employee to being an entrepreneur. Through her program, she ignited my path to building a successful business.  Seek out a mentor who has done it before, and he or she will help you to steer and guide your ship. I’ve worked with many mentors one-on-one and many I’ve never met, by reading all of their books or doing their online programs. I’m not saying you should copy your mentors… Just emulate them and put your own spin on it. If you really like the way they do something, take their lead and put your own story to it.

Lesson #3:  Stay focused on your Why. 

So many times we lose our way, and we get frustrated, and then we can’t find our focus. When you lose your way, come back to why you started the business in the first place.  Why are you doing this work that you were born to do?  A lot of times when we get immersed in the day-to-day work of building a business or working with clients, we end up saying “yes” to everything. I once was a people pleaser so I wanted to please everyone—but that took me away from my Why –why I was doing this work in the first place. Over committing ourselves to everything and trying to please everyone takes us away from our own unique gifts and what we are truly born to do.  When we stay focused on our why, we stay focused on why and how we’re serving others. When we don’t stay focused on our why, it can lead to huge amounts of frustration and resentment. When you take on something new, ask yourself “Is this moving me forward? Is this helping me to achieve my highest potential? Am I bringing my best self in this situation and am I helping others to bring their best self?”

Lesson #4:   Learn to break things into small actionable pieces. Slow and steady wins the race! 

I always tell my clients, overwhelm is the biggest killer of dreams. So many people tend to look at the big project, and think to themselves, “Oh my gosh, this is so overwhelming!”  I’ve learned that overwhelm can really trip you up and sometimes turns into actually avoiding the important work you need to do. They try to attack a big giant project, event, or a goal, all at once and they get frustrated. Then guess what happens? They end up quitting. What I tell people to do instead is, to take that big project or idea and break it into small, actionable pieces. We don’t eat a giant pizza in one big bite!  We break it up into small pieces, and then we can chew it even better. Starting small, slow, and just steady. Work on something every day that will move you forward. Then there aren’t enormous, overwhelming tasks looming over you, that tend to cause paralysis. Take an hour every day and work on moving yourself forward, work on moving your dreams forward.

Lesson #5:  Change your mindset to a motivation mindset. 

Changing to a motivation mindset is powerful. It simply means, having hope in the possibility of what could happen.  It’s not the desperate, “I’m going to earn a million dollars,” kind of hope, but that hope of what’s possible. Think about it. Have you noticed what’s possible when we can look at situations and, instead of looking at the bad; look at what’s gone right? Learn to focus on what is going right, not always on what’s going wrong.  This is what is called “honoring the struggle”. 

I ask God in my meditation every day, “With everything I’ve learned and everything that I’ve done and experienced, how can I take all of that and serve beyond myself?” That was something I heard from Oprah that shifted my focus. Creating that grandest vision for our life and focusing on what is possible is so important… because whatever we believe and whatever we’re thinking will become our reality.  

When you’re frustrated and feel like “What the heck am I doing?!” (because let’s face it, we all do), remember these five lessons to help you get moving again. If you’re struggling, I believe these five tips will move you forward.   It is possible, if you believe it is possible.  Let go of trying to force what the outcome is going to be, and give it up to a higher source. Because if you believe in your ability and you have that grand vision, the Universe is going to give you the courage and the energy to make it happen.  

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