How to Get Clear on What ‘Having It All’ Means for You

Jenna Kutcher 

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November 21, 2022


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Having a ‘dream’ or vision for your life can look great on paper, but in practice, more often than not, can start to feel overwhelming. How is someone supposed to actually juggle a career alongside, well, anything else? Time for adventure, family, community, rest, creativity? All signs start pointing to burnout. And I’m passionate about showing you that the ‘having it all’ burnout only happens when we let other people define it for us. That’s why I wanted to sit down with my friend and truly brilliant leader, Lewis Howes, on his podcast School of Greatness! 

This conversation felt so perfectly timed. If you’re not already a student of the School of Greatness, then make sure you subscribe and listen in — my takeaways are always profoundly simple and super applicable.

As I listened to this episode on his show, I found myself wanting to make sure YOU heard these words. We dive into why it’s SO important to invest in yourself, and what it really looks like to overcome the doubt and fear that holds us back from doing that wholeheartedly. The themes and messages here are truly meant for you, Goal Diggers, so I am grateful that Lewis let me share this conversation here with you, too! 

Finding balance in success

There are times in your life when there’s this line in the sand where there is a very clear before and after, like where you see a massive transformation. And joining Lewis’s Mastermind course was the first time I really invested in myself in a big way. Lewis kicked off our conversation by asking me, “What was the kind of a pivotal moment after the Mastermind where you realized things can take off financially and you don’t have to overextend yourself?” 

I told him that being in the Mastermind for me, as someone who lives in small-town Minnesota, I had literally never been in a room with people who could say, “I desire wealth,” or “I desire freedom,” or “I desire flexibility.” It was so crazy for me to be around people who were unapologetic about their pursuits, whatever their pursuits looked like, whether it was financial or lifestyle or flexibility. And it was the first time that I was around people who said, “Here’s what I’m going after.” So it really opened my eyes to like this new world because I feel like before joining Lewis’s Mastermind, I was so lonely in the pursuit and I also felt like, ‘why do I want these things?’ or, ‘am I hitting my own glass ceiling?’ 

I think a lot of us achievers are prone to overextending ourselves, it’s like the cycle. But I’ve recognized time and time again that success shouldn’t look a certain way, it should feel a certain way. And when I stay in alignment with how it should feel, I am so much more at peace and not in the pursuit of this frantic pace. For me, success feels like peace and it feels like no urgency.

Getting out of pride’s chokehold

Lewis and I got onto the topic of asking for help, which has always been a personal challenge for me. I mean, asking for help is the worst, right? I have a chapter in my book about how I was in pride’s utter chokehold, like, I want to do it all and be it all and all these things. And I thought, ‘no one can possibly love this the way I do, no one can possibly do anything the way I do.’ How many of us have felt that way? 

And so the chapter in the book is about how when we accept help and when we learn how to ask for it, we are so enriched. There are so many people in our lives that love just being the helper. And when I say just being the helper, I mean like being the helper is transforming lives. 

I’ve discovered in business that there are very few things that only we can do. You have to be the face and the voice, you are the visionary, but your team is like the missionaries. They are the ground workers, the copywriters, the people helping spread the mission. For me, it always felt like I was white-knuckling things. And when I finally released it and opened my hands to what’s possible, what was possible was building a massive business and having support and creating systems and inviting people in to do work that they’re passionate about that I don’t want to do.

Reclaiming your time

Lewis asked me how I learned to believe that I was capable of earning more and what the deciding factor was for unlocking more for me. I told him about the day that I hit six figures as a wedding photographer. For me that was a massive goal, I built a six-figure photography business in three years flat. I shot every weekend. I had no time off. I missed weddings. I missed time with my family. And I remember the day that I hit six figures felt like crap. I was empty. I was burnt out. I remember standing in the shower and being like, ‘why aren’t the angels singing? Where is the confetti?’ Because I thought this would feel different.

I was just so tired. I was the bone-deep kind of tired, and I had built this business and hit this goal and it felt terrible. So I asked Drew what he thought about me stepping back and taking on less work, even though it meant less money because I was about ready to chuck my camera out the window. And when I got my time back again, it was when I was creative again and curious again. My eyes would’ve never been open to any of this world if I would’ve stayed on the hamster wheel and just kept working more and more and more. And when I freed up my time, I ended up figuring out ways to unlock how to make more money.

You have to establish what is your enough point. Like what do you need to feel safety and security, and you need to draw a line in the sand and not book beyond it. It’s not sexy, but you need your time to figure out what’s next. So many of us just keep filling up our plates at the buffet and we’re so full, it’s like we can’t even think of the next meal. We’re working so hard that like, how could we have an idea or a vision or do research or curiosity when we’re so overwhelmed with what’s already in front of us? It’s wild to me because I only unlocked that potential when time became more important than money. And every single time I’ve done that, where I’ve claimed back my time, I’ve unlocked all these other ideas and I’ve gotten back my creativity. 

More from Lewis Howes

There’s a difference in going from just talking about ‘success’ in other people’s lives, or even in our own ‘someday’ scenarios, to REALLY defining what success and happiness and peace look like for us. This is the distinction that Lewis and I are drawing together here, that success shouldn’t just look a certain way, it should feel a way that looks different for you. 

I am so glad I got to share this conversation with you, and I hope you enjoy tuning into more of Lewis’ amazing conversations he creates space for on School of Greatness. Don’t miss your chance to pick up what he’s droppin’ over there. Lean in and listen on your favorite podcast app, and let your takeaways encourage you to boldly redefine the kind of life you’re creating, even 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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