The Life Cycle of an Entrepreneur

Jenna Kutcher 

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December 2, 2016




It’s funny, isn’t it? That you’d rather work 80 hours for yourself than punch a time close for 40 hours for anyone else. But if we’re really getting honest, being an entrepreneur isn’t half as beautiful/glamorous/picture perfect as we are led to believe it is on social media. We scroll and see these brightly lit office spaces (furnished with the latest Restoration Hardware desks), the midday lunches complete with mimosas, and the posts of people “casually working” from a cafe in Paris with a perfectly dripped latte and a chocolate croissant to boot…

…And suddenly, our life isn’t enough.

We look down at yesterday’s tee shirt (with ketchup stains), our lack of a bra, the desk that is covered with to-do lists (that don’t seem to be getting done) and coffee rings from yesterday’s coffee with the last few drops staining the bottom of the mug that needs to be cleaned. Sound familiar? Or am I just talking about myself right now… either way, you might be able to relate. It doesn’t mean you aren’t good enough or talented enough, it doesn’t mean that you’re not perfect enough or you’re lacking – in fact, behind those Instagram photos, chances are our lives all look pretty similar.

The Life Cycle of an Entrepreneur

You wake up, so excited that if you reeeealllly wanted to, you could hit the “snooze!” BUT, you don’t because you’ve got crap to get done and lot’s of it. The fact that if you really need a nap (you can take it) helps you roll out of bed and into the office – funny, your office is just steps away from the spot you sleep. Convenient? Sure. Does it suck you in sometimes, YES. You’re excited, inspired, and waiting for your inbox (and caffeine) to load. When that screen pops up and you see that little number next to the word “inbox” your breath is taken away and you go into survival mode.

That to-do list? Forget about it – you’re putting out inbox fires left and right and you’re questioning everything (and wishing you could just delete and pretend they didn’t land there.) You finally can breathe again, you’re ready to actually start to tackle those items that you wanted to accomplish today when you realize it’s already 2PM. What happened to lunch? (Or even breakfast.) I mean, who needs food? A lean cuisine and some Doritos will have to do.

The afternoon rolls around and you’re hating the word “girlboss…”

and catching yourself day dreaming about that windowless office you couldn’t wait to get out of… I mean, punching a time clock sounds great right about now (because you honestly haven’t crossed off a single thing on that list that needs to get done!) You doubt everything, absolutely everything, and start scrolling Instagram praying that with every swipe of your thumb, you’ll find something that lights a fire under your bum. You resort to laying out a mug, a planner (that you quick jot things down in, so it looks like you’re actually organized enough to keep a planner) and your Warby Parker glasses (because all real entrepreneurs wear those, duh!) You snap a pic and post something whimsical so that everyone else might think that you’re rocking this whole thing.

Suddenly, the “likes” start rolling in and you’re on top of the world. Is this what Rose felt like on the Titanic when she outstretched her arms and pointed her face to the sun? Yes, yes it is. You ride that high and start pumping out content. You hit “publish” on a blog post, post a photo to Facebook, and actually start crossing things off of the mental to-do list (that looks like an internet browser with a million tabs open!) How could you ever question your worth? You are AMAZING, inspired, and THE best at what you do! You close the office door with a feeling of pure triumph and a little tear squeaks out of your eyeball as you question how you could ever imagine doing anything else with this one sweet life you’ve been given…

Can you relate? Tell us about being an entrepreneur!



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  1. Yara Miora says:

    Full disclosure right here.. I’m too scared to take the plunge cause I am a snoozer and procrastinator and am deadly afraid I’m setting myself up for failure. and I know I know I shouldn’t think of it that way.. but everytime I think “Yes Yara you should just take that step and go for it at full force” – that thought is immediately followed by “But who do you think you are honey? why would people be interested in what you have to say?

    I’m so inspired by your drive and honesty Jenna these posts are wonderful!


  2. Katie says:

    This is amazing Jenna. And my dream, one day…

    Katie | WillowAndWhiteBlog.com

  3. Hahahah!! I enjoyed reading this immensely. My husband and I are parentpreneurs, so take everything you wrote and add a few kids related items. For instance, you finally got your focus going and feel like your on a roll and then the potty training kid comes in saying he needs to pee, the older kid comes in to tell you to come look at the lego structure he just built, and the baby starts crying because she’s hungry. So you take the 2 year old to the potty, praise the 5 year old and latch the baby on the boob and pray that you get 15 minutes to focus completely on the task at hand. AND before you know it, it’s lunch time and you can’t skip making it because you have to feed the kids! : )) Yet somehow this is what we want, I love having my husband home and working together in our office, rather than him at work, and me floundering by myself at home. : )

  4. Success in Business includes Cultivating a Grateful Heart - Reina + Co says:

    […] Kutcher talked about the life cycle of the entrepreneur and I think she couldn’t be more correct. Also, please see the graphic she created and chuckle […]

  5. Lexdaresyou says:

    Wow. My best friend and I were just exchanging entrepreneurial distress yesterday and today I feel as if I am the most powerful CEO that ever walked this planet.

    You hit the nail on the head Jenna. Thank you so much for sharing this extremely relatable thought. <3

  6. Amanda says:

    This is perfect, Jenna! Sometimes I need someone who just gets it. So nice to know I’m not the only one who feels this way!

  7. Maria says:

    Story of my life. As a new entrepreneur/blogger I am constantly finding myself in the comparison trap. What helps me move forward is reciting these helpful words- “don’t compare your beginning to someone else’s middle”. Everyone starts somewhere. Heck, I don’t even have a desk (living room table, check!) Giving my best is all I can do, and that’s something to be proud of. Thanks for being so real and inspiring!

  8. Beth says:

    I just started an online sleep coaching business, and I’m still working my full-time job. I thought it was the perfect position to be in because I still have income coming-in while I’m working on my start-up, but It’s been TOUGH. By the time I get home from my 9-5, I just want to eat dinner and go to bed, not work on my other business! What’s also tough is I work with sleep habits, so I have to make sure I practice what I preach! I’ve started getting up at 5am so I have time to work on my business before work. I went on vacation last week and slept my whole first day. Guess it was more exhausting than I thought! Still love it and can’t wait to be thriving in my new career though! Thanks for your honesty… it’s nice knowing I’m not the only one who has crazy emotions about this!


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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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