The Early Entrepreneur Days I’ve Never Talked About Before

Jenna Kutcher 

posted by:

Previous Post




July 29, 2020


Tune In: Apple Podcasts | Spotify | Stitcher

Why not switch things up a bit? I’m tossing my interviewer hat to Kylie, the manager for the Goal Digger Podcast, and she’s putting me in the hot seat. Getting interviewed always brings out stories I’ve never thought to share, or methods and strategies that I’ve never revealed before.

In this episode, Kylie will take us back in time to my early days, when I was fresh on the full-time entrepreneur scene, still gaining my footing, and riding the learning curves alllll the way to right now. If you want to know how I invested in myself at the beginning, which early days marketing strategies I still use right now, and which of my business fears actually came true. Hit play for the full episode and to hear my answers to the questions below.

Quitting My Job

Kylie asked me about the days leading up to quitting my job, and then what it was like to actually give my notice knowing I would soon be my own boss. I told her a story I’ve never shared on the show before… My last day in the corporate world was actually unexpected due to an injury, so I didn’t have a last day of work filled with fanfare.

She also asked: What did day one of being my own boss full-time feel like? At that time, was I more of a “prove myself right” person or “prove them wrong” person? In other words, was my motivation or empowerment internal or more external? And who and what was I following to lead me through this new journey?

We also talked about the first major investment I made for my business that I actually wouldn’t recommend today. Hit play to hear the answers to all of these questions and more.

Early Lessons I’ll Never Forget

When you’re a beginner at anything, you don’t know what you don’t know, right? That was true for me when I started as a full-time entrepreneur as well. Kylie and I talked about learning curves and the burnout myth we’re sold when we get into business for ourselves.

One lesson I learned in my early days was that work-life balance doesn’t truly exist. But even more than that, I was learning that my way of running my business didn’t have to be like everyone else. This idea that you have to hustle and work yourself into the ground to be successful just didn’t match the reasons why I wanted to be an entrepreneur in the first place.

Kylie also asked me to share my checklist for evaluating opportunities and saying no to the ones that aren’t right for me, my family, or my business. If you want my boundary setting strategy, tune into the full episode on your favorite platform linked above.

What’s Still Working Now

As I prepared for this conversation with Kylie, I found myself looking back at my earliest work. My social media posts, the emails I sent to my list, the ways I was showing up for my clients (and potential clients). And you know what? Not much as changed.

My messaging has always been around possibilities and encouragement, but the way I deliver those messages has become more refined.

Kylie asked me to sum it up in three points — What 3 steps or strategies have always brought me success when pursuing a goal, whether it be hitting a sales goal or getting engagement on an Instagram photo or creating something new? Press play to hear the three components of my methods that have remained part of my business since day one.

The Big Picture

In this interview with myself in the hot seat, Kylie asks me about navigating my earliest business fears, the learning curves that taught me so much, and the pieces of entrepreneurship I left behind. What do you think? After tuning in, do you want more of this style episode? Join the conversation on Instagram @goaldiggerpodcast and let us know what you think!

Thank You to Our Goal Digger Sponsors

Get 10% off your Primally Pure purchase

Save 20% on your Tonic site with code: GOALDIGGER

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Kym Kitching-Downs says:

    Thankyou once again. You truly inspire the entrepreneur in me.

    Great hearing your journey.

    Good luck with the potty training>


The Latest From the Goal Digger Podcast

BINGE listens


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). 

hey there!


What do you want to read today?

Except instead of a video game, this is you IRL. Let’s get laser focused on setting your goals for this month, year, and beyond so I can hand over resources specific to how YOU want to grow!

Take The Quiz!



free downloads show


Free downloads to elevate your game.

FREE challenge



Screw the junk mail, I'm bringing "real" right to your inbox. Deep encouragement, tough questions, needle-moving challenges, and smart strategies to help you make your dream work. You in?

great idea alert!

Hey, Let's Be Pen Pals!





|    Legal