The 3 Things I Wish I’d Done Sooner

Jenna Kutcher 

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April 15, 2020


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You know what they say, hindsight is always 20-20. And honestly, it’s funny looking back at life and realizing just how many things we could’ve done better, streamlined sooner or simply made smarter decisions about. I’m not an advocate of living with any regrets, but I do think looking at our past is a valuable way to see just how far we’ve come and what we can do better going forward.

And while I’ve shared so many challenges and mistakes on the podcast that I’ve learned from and adjusted through the years, today I want to talk about a few things I haven’t touched on a whole lot in this space.

I’m SO NOT into living a life with regrets and I firmly do believe that everything happens for a reason: our missteps and mishaps and challenges and everything in between. So this is totally NOT about living in the past and being bummed about things I’ve done wrong — it’s truly more about pinpointing the things I’ve learned to hopefully share with you and save you from potential regrets or heartache or frustration.

Curious about the choices I wish I’d made sooner? Keep on listening to hear what I’ve learned lately and how it’s impacting the way I do life and business.

Planning for retirement and saving money

Did you know one-third of small business owners don’t have a retirement savings plan set up?! 21 percent of them used previous retirement savings just to start or grow their own business, and 18 percent hope to sell their business down the line to fund their retirement.

That’s a lot of people dipping into their future to be able to fund their present, when I’m really not so sure that’s how it should go. And the scariest number of all in my opinion is that 12 percent of small biz owners do not have plans to retire — LIKE EVER — and another 12 percent don’t see the need to save for retirement. An entire 40 percent just aren’t confident they’ll be able to retire before the age of 65.

For so many people in traditional jobs, all of this is planned out for you and predestined. You sign up for your 401k and set it up so a portion of your paychecks go into it, and if you’re lucky your employer puts some in for you too. Bada boom bada bing, you have a retirement plan. And traditional workplaces also commonly have leadership and consultants come in to advise and explain what the best savings tactics are and how you can get the most out of your savings.

It’s almost a nonnegotiable to get all of this set up, but as an entrepreneur it can feel like a choose your own adventure style process — and a lot of people choose to forego the adventure because there’s too much on their plates to handle in the present to be concerned about their future.

Now, when I first started my business, I was just an LLC so I could only tuck away a certain amount of money a year for retirement because there’s a cap with LLCs. For me, it was $5,500 each year, which honestly wasn’t bad.

But then when we changed my filing to be an S-Corp and I was able to put aside ten times the amount of retirement savings and that difference is astronomical. Now I’m not saying you should up and change from LLC to S-Corp — that’s a conversation worth having with an accountant or trusted financial advisor because it’s different for every kind of business. I was advised by our accountants on how and what to do, but looking at how I can set aside ten times the amount of money year after year, that makes a giant difference.

When it comes to financials, this is just a small example of ways to get creative with financing your future and we’ve checked and double checked all the legalities with a team to ensure that we’re doing everything correctly but also setting it up so that how we live today supports a greater future. I wish I’d known all I know now about savings and retirement and investing and allll the possibilities back when I started out because Lord knows I would’ve been way more cognizant of where I was putting my money and how I could’ve harnessed even a small amount to save for our future starting earlier on.

On this same note of saving for our retirement, I’ve also learned that planning for the future entails living a life right NOW that we’ll be proud of in the future. I used to be scared to spend money on things I like or that would make my life more convenient, but honestly we work too dang hard to NOT enjoy the fruits of our labor — in moderation of course. I just know that we want to be set up well for our future but also not live in fear or restriction in the right now, and so finding that delicate balance of enjoying our blessings today WHILE planning for the future has been such a valuable lesson in living life with an abundance mindset.

Letting go and passing the torch

I’ve talked a lot about how hiring was a tough concept for me at first but it’s more than just hiring. It’s the idea that I’ve always had a hard time letting go of control and passing off what I consider MY responsibilities into the hands of anyone else — even people that I know, love, and trust! I mean, this business is my baby. For five years I worked alone day and night, I wore all the hats, I did all the things, made all the decisions, it was just me.

We are control freaks because we CARE. And that is so dang beautiful and likely why you’re successful at what you do in the first place. All good things, BUT there comes a time where you realize that done is better than perfect and your grip on control loosens and your hands are opened for life’s possibilities again and you remember what it was like to not feel like a hamster on a wheel.

It has ALWAYS been a challenge for me to pass the torch and trust that things won’t just totally implode. I know I know, dramatic much? But for real, it’s just been something that’s taken me a long time to fully understand that support is a GOOD thing, accepting help is wise, and trusting others is actually the BEST way to grow my business and give me the thing I ultimately want: success.

It was a slow transition going from absolutely not wanting to outsource a single thing to hiring one person to two to now over ten and now finally being in a place where I’m the visionary, the overseer who still has a hand in every single aspect of my business, who still has that same heart and desire for impact but who isn’t the one managing and implementing all the things on a day to day basis.

Now, let me give it to you straight — I’m not just sitting back and collecting paychecks while everyone else does the work in my business. I am not hands off by any stretch of the imagination. I have simply gone from working IN my business day in and out to working ON it and that change alone is something I wish I had done and learned way sooner.

Over the past few years, I’ve filled my team with women who legit specialize in the different tasks they take on with me, and we’ve even moved some of them around to get them in their exact expert spots where they can excel and love the work they do.

I still see, edit, tweak, proof, write and sign off on every single piece of content and resource we put out — the difference is that I’m not the one building everything from the ground up. I’m not the only one moving the needly forward. In surrounding myself with talented, specialized, passionate women who own their specific corners of my business, I’ve allowed the business to flourish and grow more than I ever could have taken it on my own. Like WAY more.

Defining what we will share online

The third thing I wish I’d done sooner was defining what we will share and what we will keep private online. Now it might come as a surprise that the gal who shares pics in my bikinis and posts about the struggles of loving the skin you’re in, navigating loss, and figuring out how to run a business and be a mama gracefully, actually holds back online in many ways. Most of the time when I meet people in real life, they tell me they feel like they know me and it’s the greatest compliment in the world because my sole purpose of being online is to actually connect with other humans.

I love sharing so many of our wins, challenges and learning moments with others, but it may also be surprising that I’m actually a way more private person than you’d expect or ever know, and I’m becoming more and more private as I grow older and do life with my little fam.

Before you take my wanting privacy as a lack of authenticity, I want for you to know that what I share on a day to day basis is ALL me, all my heart. But here’s the thing: you can connect without disclosing every detail of your life.

It’s wildly important for me to feel like we have a real relationship, me and you, and while I do discuss some intimate pieces of our lives that I am comfortable with, from our miscarriages and body image to motherhood struggles, I am also super careful about how and what I speak about and share online.

Whenever I share, it’s always MY story — my version, my narrative to tell — and I’m very careful to not speak for others. If a story involves someone else, I always ask for permission to give the people in my life the decision over whether or not their piece is shared with hundreds of thousands of people.

I think what happened is the pendulum swung hard with the #authentic movement and people started to think that keeping it real was airing your dirty laundry out for the world and I think I’ve just learned that I don’t always need to disclose every little thing that’s happening behind the scenes and in my world, I don’t owe anyone an explanation or information and that is so freeing to remember.

My personal approach to authenticity is sharing my true heart and real feelings but I also don’t air my dirty laundry or disclose personal things with strangers on the internet like when I’m fighting with Drew or navigating weird family stuff or grieving a personal loss — which by the way, I do face those things! Everyone does, but it’s just not something I think is fair to my loved ones to share with the world.

As a mom, I’ve definitely dialed back what I share about Coco and I’m 100% sure I’ve messed up here and there but overall I believe her story is hers only to share and so it’s been challenging to navigate what I can share as her mom vs. what is simply her story and not mine to tell and how I let people celebrate this baby that we prayed for for years while protecting her. If anyone figures this out, holler at your girl, but dang, there isn’t a guidebook out there for all of this, is there?

The point? Set boundaries, talk with your loved ones, establish what you’d feel comfortable sharing with a stranger on an airplane and draw lines in the sand of what’s off limits. You can be real and authentic without sharing every detail of your life, you can change your mind, shift gears, change the narrative. We’re all learning as we go, am I right. I just wish I had figured out that I can keep it real and still maintain a private life that feels safe for myself a bit sooner!

I wasn’t always so aware of what I was posting and protecting parts of my life, but I think as I’ve matured I’ve realized the things that are precious to me are okay to keep to myself.

The Big Picture

What a wild array of topics, am I right? I mean I went from financials and money talk to mindset shifts around letting go of control, to privacy and authenticity online. I mean, life’s lessons aren’t always linear, right?

So seriously, are you surprised to hear these things I wish I’d done sooner in life and in business? I think we ALL realize more about ourselves as we get older. Growing older kind of gives us this new, clearer lens to look back at the mistakes we’ve made, as we gain more experience and knowledge under our belts.

It’s honestly just the natural progression of life and while I wish I’d made these choices sooner, I also know that I had to learn through navigating the difficult seasons and mess ups I’ve made to get to where I am today. I mean, I wouldn’t trade this knowledge I have now for anything. While mistakes are inevitable, it’s what we do with them and how we progress and grow afterward that’s all the more impactful. I hope my lessons help you to navigate and protect your own world a little more too! Your future self will be ready to thank you.



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  1. Rebecca says:

    I so appreciate your thoughts on defining what you’ll share online! You absolutely can be authentic, but still keep some parts of your life private. I love your authentic voice, but you absolutely don’t have to share EVERYTHING and still be authentic.


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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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