10 Surprising Lessons Learned in the Last Decade

Jenna Kutcher 

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December 18, 2019


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How the heck has another year come and gone? I’m doing a FULL recap of my year and running through the numbers but I’m feeling all sorts of nostalgia as we approach a new decade and I think it’s time to really reflect on the lessons I’ve learned, what’s gone well and moments I will always cherish.

It’s just as important to me to dig into how I’ve messed up, how I’ve grown, pivoted, and transformed. The best thing about being a human is that we are constantly changing and so let’s take a look at the biggest things this past decade has taught me.

Lesson One

Don’t let anyone define what success looks like for you, define it yourself.

If we rewound to a decade ago, I was interning at Target and planning out my entire future. At the age of 21 I was dreaming of my life outside of college and imagining what it would be. I knew Drew and I would get married — we actually planned our wedding the night we started officially dating and told our best friends they would have to walk down the aisle together and guess what? They did.

But beyond that, I had this vision of corporate success that had been painted for me from textbooks and society. I envisioned a powerful business woman looking like a gal who wore business suits and high heels and I dreamt about climbing that ladder — heck, scaling it, to keep moving up and up and up.

I used to tease that I wanted a husband who stayed home with the kids and had dinner ready when I got home at the end of a long day, talk about manifesting right? Though you wouldn’t catch me dead in something that required dry cleaning.

I think the greatest lesson I’ve learned in this last decade is to not let anyone define success for me, because every time I’ve chased someone else’s version of it, I’ve “arrived” and realized that I worked my butt off to get somewhere I didn’t want to be.

From the corporate ladder climb to that “six-figure” number, to shooting more and more weddings or being on the road all the time for work… none of those things actually made me happy like I thought they would.

This year when I imagined success, I wrote down the word FREEDOM. To me, I’ve finally realized success isn’t things, it’s not extravagant accessories, or jet setting every week, to me it’s freedom of time and schedule. I want to wake up every morning and feel free to choose what I do, whether it’s read the same book to Conley for the 18th time or work on my next big project.

It took me a long time to put the blinders on and stop looking at what everyone else was doing and letting that influence what I was chasing. When I finally defined MY version of success, I found it and let that vision lead me in all of my decisions day in and out, and boy does it feel good.

Lesson Two

You’re going to have to hustle for what you want, but don’t adopt hustle as the new norm — aim to use that mode sparingly.

You know me, I have this sort of love/hate relationship with the word hustle because I think it’s necessary but what I hate is that it’s become the new norm. This glorification of busy has taken over and THAT is something I want to change — the positive narrative around hustle. When I look back at the last 9 years of pursuing entrepreneurship, there were absolutely seasons of hustle, seasons of grind, but I am thankful that I didn’t allow that to become my autopilot.

I battle with this all the time because hustle was a HUGE part of my story. I worked morning, noon, and night on my dream, I had crappy boundaries, said “yes” too much, and I filled my calendar until one day I just couldn’t do it anymore. It was this realization that I had created this treadmill I couldn’t get off of and it was the worst feeling in the world.

Maybe I can’t save you from hitting burnout, because maybe burn out is an important threshold to help you define enough but if this last decade taught me anything, it’s that my business transformed massively during the seasons I gave myself margin. Then when I chose to grind and jump on that hustle wheel, I could go at it full force from a place of rest, not overwhelm, and the quality of work was so much better. So take that note and apply it. Margin gave me more impact that hustle ever has.

Lesson Three

You CAN do everything and you should for a season, but if you really want to grow, grow with others.

I’ve literally played every single role in my business. What you see today is incredibly different than how it all began. Over the last decade I’ve been the CEO, the head of marketing, the accountant, the designer, the web coder, the copywriter, the content publisher, the inbox support, the course creator… You name it, I’ve played every single role and chances are, you probably wear many hats right now, too.

The crazy thing is, I was super afraid to hire. I told myself so many lies: I can’t afford it, my business isn’t big enough to hire, I can do everything myself, I don’t trust anyone with my business. I think all of those thoughts are natural, but there’s that quote, if you want to go fast, go alone, if you want to go far, go together. I look at the many facets of my business and they simply wouldn’t be possible without my team of ten behind them.

What’s beautiful about entrepreneurship is that you grow with your business, you learn new things, and you master aspects you never even knew about, but it’s important to know that just because you CAN do all the things doesn’t mean you should. I have countless episodes about hiring and outsourcing and I can confidently say that I am now in my genius spot and that my team fills in the roles where they are operating in THEIR genius spots to serve the bigger brand.

Lesson Four

Value your time — like every minute of it and treat it like it’s your currency.

Almost a decade ago, I got paid for the first time to take photos and I was HOOKED on entrepreneurship. It shouldn’t be a shock that the girl who ran lemonade stands on a minimally travelled dirt road became an entrepreneur, but that’s another story for another day.

The truth is, when I got paid that first $100, I felt RICH. I couldn’t believe I was getting paid to do what I love and I made a mistake you might be making right now: I thought to myself, oh my gosh, I just got paid $100 for an hour of work, holy cow. It was like I was seeing money signs.

Except that I didn’t realize that I was spending WAY more than an hour on the shoot. I had to prepare for it, I had to get there, I had to shoot, I had to edit, and blog and deliver and a million other things. In fact, if I did the honest math, I was probably making less than the fry guy at McDonald’s, especially after paying taxes.

It’s a common mistake: we don’t value our time and one of the biggest reasons is because we LOVE what we do, right? That’s why we start a business, hopefully to get paid to do what we love and so often work doesn’t FEEL like work, but here’s the thing: you have to learn to value your time.

When I look at the last decade, one of the biggest ways I’ve changed is how I fiercely protect every minute of my time these days. If it’s not growing my ability to impact others or hang with my fam, it’s out. I’ve said it before but time is my currency, I make decisions based off of my time, not money and I know my worth — which is not something I could have said a decade ago.

Lesson Five

Every season has a purpose, even the hard ones. Embrace the one you’re in and use it to work towards where you want to go.

This was a harder lesson to learn, because it meant navigating hard seasons and uncharted territories. When I look back over the last decade one of the biggest teachers for us was loss, specifically through miscarriage.

It’s wild thinking back 10 years ago, when Drew and I were starting our relationship and dreaming about our future. It might surprise you but we both said we didn’t want to have kids and we meant it, for a solid five years of married life. We loved our lives, our freedom, our time together… and then something in our hearts softened to the idea and it felt like God hit a switch in us that led us to imagine growing a family.

We never envisioned it taking so long or being so riddled with loss and it could be really easy to write off that three year journey as a terrible one but instead, I see it now as our best teacher and motivation.

I know that it’s not always possible and when you’re in the thick of a hard or heartbreaking season, the last thing you want to look for is joy, but if you can just let each season teach you the lessons you’re meant to learn and keep your head down working on the things you CAN control. When that season ends, you’ll be thankful you worked while you waited it out.

The Other Five Lessons

Press play on this episode right now to hear the other five lessons I’ve learned in the last decade. This episode was almost therapeutic for me. Looking back on ten whole years of life, entrepreneurship, and more was eye-opening. I limited this to 10 lessons but let’s be honest, I’ve learned a million things along the way.

If I could go back and talk to my 21 year old self I’d tell her that her life is going to be bigger and better than she could even fathom. It won’t be without hardship but it will be entirely worth it. I’d tell her to stay grounded, keep her head down, get clear on what she wants and never stop dreaming bigger. Who’s ready for a new decade? A fresh start, a chance to learn and grow and be a better version of the person who’s listening to this show right now.


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  1. So many great nuggets to learn from! Thank you for sharing, as always! I’m working on the hustle lesson in my life right now.


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Before you get any further... Hi! I'm Jenna Kutcher!

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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