Three Things I Have Learned as an Entrepreneur

Jenna Kutcher 

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March 2, 2016



Going into year five of owning a business, it’s crazy to think that so much time has passed since I said, “I have a dream and I’m going for it.” To be honest, each day that my alarm goes off and I know I get to stay home, snuggle my pups, and work from the couch (ahem, I mean, my office) is a blessing. I still don’t take that for granted – not even one bit. This life as an entrepreneur is filled with curve balls, tough days, nap times, and the blessing of being your own boss (which can really be a blessing and a curse if we’re really being honest!)

  • Real pants will become a challenge: Sounds silly right? I wish I was kidding but I run my life around not having to wear real pants (or any pants at all.) I mean, I live in yoga pants 90% of my life (still waiting for a brand to sponsor my obsession, that’s the dream!) Somewhere along the way I became a hermit. It wasn’t intentional, but I noticed my favorite days were the ones where my schedule contained only online hustle (that was best completed in anything but pants with a zipper and button.) You get spoiled not having to worry about pants (or heaven forbid: a bra) and that spoiled-ness totally creeps into your mind and you strategically plan your week out in order to spend the least amount of time in real pants. I’ve gone weeks without make up and I don’t miss it one bit.
  • You will fail but you will go on: Somehow we act like our failures never happened, these moments clearly don’t show up in our Instagram feeds or as blog posts, but they happen to all of us. We can’t imagine anyone else having gone through things like we are encountering, so we feel alone navigating the island isolated. We can’t pretend that we’ve never had those seasons in chasing our dreams where it feels like we’ve been sucker punched and we’re plagued with the “can’t eat/can’t sleep/can’t do this anymore” feelings. Going into a business, I knew it would be hard work but I didn’t know there would be times where I felt like the wind was literally sucked out of me. The truth? You move on, you’ll be alright, and you’re doing the best you can. People will forget that you are only human, you will make mistakes, and that you’re doing the best you can – but it’s okay, it’s going to be okay. Look for clients who will support you as you are, will welcome your human tendencies, and will extend grace when you need it (because you will need it, that’s for sure.)
  • Lastly, you will never “make it.” Truth be told, I have yet to have a moment where I tell myself, “Jenna, you’ve made it.” No amount of awards or followers or clients will ever make me feel like I am done chasing. I think that’s part of the chase is that it’s never done (and I’m okay with that.) It’s easy to look at others and see their lives, their accomplishments and to subconsciously tell yourself that they, in fact, have “made it” but I bet my bottom dollar that if you asked them, they would say they are still working towards it. Whatever “it” may be. You’ll see others successes and yearn for them to be a part of your story but the truth is, we all have such unique paths on this earth. Where you are is exactly where you should be, just trust me. Part of the entrepreneurial journey is transforming as your life changes, your goals change, and your business evolves. It’s a process that will never be complete. It can drain you and inspire you, it can suck the living daylights out of you, or leave you feverishly typing into the wee hours of the morning when you are struck with inspiration, either way, it’s a beautiful ride we are on and one I don’t take for granted.

Running a business isn’t for the faint of heart. It isn’t always glamorous, filled with perfect days in perfect houses with perfect clients. It’s a lot of hustle, a few sleepless nights (okay, lots of them) but a drive to chase the dreams that have been planted in your brain in a place too impossible to ignore. It’s a chance to leave your imprint on the world, try your hand at being your own boss, and attempting to share your gift with the world (which is pretty exceptional, if you think about it.) It’s filled with different seasons that can be thrilling to tough to enjoy but at the end of the day, it’s something you would never trade for the entire world!

What are the biggest lessons you’ve learned while chasing your dreams? Comment below!


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  1. Alex Good says:

    Hey! Whoa, my very first time posting on your blog (where’s the champagne to celebrate?!), but I wanted to contribute as I’m on the slow and steady path to working for myself. The biggest, and most difficult, lesson was realizing that my path won’t look like everyone’s, or anyone’s for that matter. I used to envy people who seemed to reach their goals overnight, but I’ve learned that my success isn’t measured by speed. I have to take risks to achieve my goals, but they need to be calculated and make sense for my journey. I’ve learned the power in keeping my eyes focused on my own work, whether or not I’m working hard and just creeping along towards my own success.
    Great post!


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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