The 6 Biggest Entrepreneur Struggles No One Talks About

Jenna Kutcher 

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November 7, 2019


Ever wonder if anyone in your life gets it? Whether you’re a novice business builder, a side hustler on her way up, or a seasoned serial entrepreneur, there are just certain things about business ownership that people in other industries or a regular 9-to-5 don’t quite understand.

But I do. I am in it, every single day, and have been for years, working weird hours, staring at my phone trying to come up with a caption, losing sleep because idea after idea for my business keep popping into mind. It’s a struggle, but one of the most rewarding, beautiful struggles I’ve ever been a part of.

And in case you’ve just been feeling like you’re on this ride solo, I want ya to know I’m here with my laptop tucked under my arm, trying to balance a baby, my to-do list, and an iced coffee right next to you. (Oh, and also like, sleep, my marriage, a social life, self care, and a little fun, too.)

Sometimes, it’s all a bit much, but that’s why it’s good to share in it, not to wallow or commiserate (at least, not totally), but to find camaraderie, common ground, and empathy with one another on this entrepreneurship journey. So if you’re on coffee number 3 of the day and need a little boost, here are the biggest entrepreneur struggles that I face in this career path all the time, just like you.

Just because you work for yourself doesn’t mean you’re available 24/7.

Ohhh, sugar. I could go on all day about this one. The amount of people who have reached out for coffee or lunch or an afternoon shopping date because they assume working from home = endless time off is wild. And I know it happens to my friends in the entrepreneurial space, too

While I do take advantage of my work flexibility occasionally, it took years of me with my head down, working 50+ hour weeks to be in a space where I felt I was in a solid enough space to take a leisurely lunch with a girlfriend. It is more than okay to set firm boundaries and let your loved ones know your office hours, which may very well be 9 to 5, and then schedule a get together on a day off or a time that works for both of you!

Your to-do list is always growing and never ending.

The gargantuan to-do list. I love it oh-so much, but I also sometimes hate it. Because it. never. stops. growing. I have a running list on my phone of ideas for my business that hit me at random times like, oh, I don’t know, when I’m asleep. And when I’m nursing, running errands, talking with a friend, or taking a trip. Knowing you, I’d bet you have a similar list in your notes section.

It’s wonderful because it means I’m constantly thinking of new ambitions to strive for, and I can track my progress as I check items off of it. But there’s just something a little unsettling (but also a little exciting, right?) about it consistently expanding and getting longer and longer. I know I can’t be alone in this love-hate relationship.

You would really LOVE to get to that personal project, but…

Or get your hair highlighted, teeth cleaned, or Target run done. I’m typing this with a nail that’s been broken for two weeks and I just haven’t had time to run to the nail salon. When we’re in the thick of building a business, it is so easy to let the other things in our lives fall to the wayside. We make excuses that they’re not as important as creating the security and success of sustaining a business.

But friend, if you’re ditching things that make you happy, or just make you feel sane, what’s the work worth at the end of your life, anyway? When you haven’t grown your dream garden or taken that trip to Greece, will you be happy in 50+ years that at least you hustled and grinded your way to the top of your industry? The things we love matter. It is okay to make space for them.

It’s hard to turn off the switch to personal mode at the end of the day.

I mean, my laptop is just screaming to be opened at all hours of the day and who really works in the those offices you see on Instagram? I mean, the couch is my space. This is the REAL struggle, y’all. I know it is for me, at least. I wear so many hats in my life, like many entrepreneurs do: boss lady, mama, wife, daughter, sister, friend. But I think because entrepreneurship takes so much of my energy, shutting it down is never an easy task.

From the ding of a new email to the vibrations of a text that could be work related. I’ve found that creating boundaries and hard stop times for myself can work wonders. I don’t want to be working through dinner or waking up to skim through a packed inbox, so I’ve placed rules around those things to enable me to embrace my other roles more fully and happily.

Time seems to fly WAY faster for you than it does for anyone else.

The days are long but the years are short? Nah, I feel like there’s never enough hours in the day. Ever been working on something and get into this rhythm that feels so good, and then look up and realize it’s 4 p.m. and most of your day is gone? It is so shocking how this can happen, and honestly, I think it happens when you’re working toward the right goals and you’re within your genius spot.

I mean, time flies when you’re having fun right? I think it also flies when we’re actively working toward the things we want and being resourceful and intentional to get there. Don’t let the lack of time bother you or freak you out. Instead, ask for help on the things you don’t have the capacity to handle. And embrace the flow when you’re in it.

You have a quiet, constant fear that something be forgotten.

This is probably the worst of all time. The WOAT, if you will. It’s that small, whispering voice that says you’re getting it all wrong, you’re missing the bigger picture, or you’re not showing up in the right way. There’s no validity behind it, but it’s convincing. And consistent.

When this voice arrives in my ear, it’s when I pause to ground into my values and my intentions with my business. I remind myself of why I do what I do — to impact others greatly and help them lead lives they adore — and then I continue showing up, day after day, to deliver on that promise, even if it’s imperfect.

I hope this helps you find some encouragement that we all face hardships in entrepreneurship, and we all have days where we feel frazzled and uncertain about where we’re at. That is totally normal, and just in case no one’s told you lately, you’re doing a wonderful job, and you are just where you’re meant to be. Keep going, friend.


Another popular blog post on this topic to check out:

10 Things No One Tells You About Working For Yourself

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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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