The Struggle is Telling the Story
I turn 39 this Friday, and I started my first biz when I was 22. It feels like a long time ago. I took $1500 of babysitting money, and over the course of the next ten years, turned it into a business doing almost two million dollars gross annually. It was awesome, until it wasn’t. Young, and lacking knowledge about leadership or business, I made some assumptions about life, my skills and abilities as a business person.
After ten years of business, the business ended up filing bankruptcy, due to a multitude of reasons. I believe in taking ownership of mistakes, so I have to say some of it was my fault; but some of it, truly, was out of my control. Ultimately, we ended up suffering from the hit of a bankruptcy roll-back, when the trustee of the bankruptcy of one of our customers came to us and asked us to pay them back the money that customer had previously paid us. We barely had the next week’s payroll, let alone the sum they were requiring of us.
Around that time, I had been working on an idea for a planner for about two years. The same week I found out we would have to file bankruptcy, we had launched Day Designer as a separate company. It was a last-ditch effort to try to make the money to keep us from filing, but it didn’t work fast enough.
Life was at the lowest of low points. Between business bankruptcy, three small kids under the age of three, and a marriage that was struggling with my husband’s own financial indiscretions, there was so much self-doubt. I felt like a fluke, and didn’t know if I had what it would take to get another business off the ground, and keep it running, sustainably.
With one business already failed, I wanted, and started praying for, a redemption story. I didn’t know what that would look like, and I didn’t expect it to be financial. I just knew I wanted to do something different with this business, this time around. It took me six months to sell the first 500 planners, and then, by the grace of God alone, sales started to double and triple.
About two years into the planner business, we were approached by Blue Sky, a company that had a relationship with mega-retailer Target, and they asked if I would ever be interested in designing products for Target. (ha!) That was the start of a licensing relationship that, under my leadership, would release three years worth of product into Target stores nationwide. In so many ways, that success was redemption enough. But as the business was succeeding, I was also starting to feel pulled in another direction—the desire to be a mom. In 2016, Blue Sky asked if I would be interested in selling, we came to an agreement, and the business was sold.
Long story (literally) short, I was on cloud nine. It felt like a literal dream come true. After four years of praying for a redemption story and having that deep, deep desire to spend more time with my kids placed on my heart, it was finally happening. I started last year so full of joy. The kids were part of a part time homeschool program, and we were going to spend that year reading books and making memories and I was going to be a “real” mom! (You know, like the ones I see on Instagram?)
And then my husband came to me. Again. In debt. Again. I won’t go into detail on this here, except to say that I have his permission to discuss this and our lives are a work in process in this area.
We were able to sell his business, by the grace of God (I should throw in an “again” for that) and now we’re this weird spot again. It feels like valley and famine, not mountain top and feast. And here’s what I’ve learned:
- It doesn’t matter how many “successes” (by the world’s definition) you’ve had in life. In that valley, at the start of every new mountain, you’ll wonder again if you have what it takes. And that means you’re human, you’re learning and growing, and thankfully, you’re humble enough to know that it’s not you at the helm anyway.
- Fear never really goes away. Starting two multi-million dollar businesses doesn’t mean I’m any less afraid to try to start a third. Having done it before isn’t a guarantee I can do it again. The fear is always there, and on top of that fear, in order to create action, I have to develop the habit of doing it scared. Start despite the fear.
- Telling the story helps lessen the fear. Telling puts that habit muscle into practice. The story is old news to me, something I want to bury under a pile of shame, which I successfully do when I DON’T tell it. But when I do tell it, I get to own it, free of shame, free to live in the light, free to encourage others.
- Comparison is the lie Satan will use to keep us from telling our stories. I know we all have stories of failures and fears, restarts and quitting, rough edges and dark spots. Those of us who feel those weights need to be a voice, especially now, in this day and age of curated perfectionism. There is nothing wrong with excellence and beauty, and we should all pursue those traits, as they are reflections of the Gospel that is so graciously offered to us all. But if we allow comparison to silence us, because we think we are not enough, we are hiding our lights, and the evidence of a merciful Savior at work in our lives.
So that’s where we are.
The story doesn’t get easier to tell or own, but it’s part of a continuous redemption story He has promised to make of my life, and that means He has tasked me—and all of us—with the telling of it.
What’s your story?
Side note: several people have asked “what’s next” for us. David is currently working on establishing a real estate career over at Front Porch Family. I’m dabbling in local retail with Gingham Home, wrestling with knowing I’ve been given entrepreneurial gifts, but also want to “just be a mom” during these long days/short years. We are praying a LOT. The best place to follow our journeys is currently over on Instagram.
Whitney, I’ve followed your story for the past 10 years and entire you to know that from afar you’ve always been an inspiration to me and picture of God’s grace and courage to move in the midst of crazy scary things. Thank you for your vulnerability and your willingness to share your journey of what many of us experience, but in the world of 1×1 perfection, don’t have the support to share. (We are very much alike in our business thinking and dabbling). The hills and valleys are real and I just want you to know that I’ve always prayed and will continue to pray for your story. In doing so, I find courage to continue on my own.
Pardon my typos. This is what happens when you use an iPhone not wearing your glasses and maybe having a glass of red at 1:30pm.
I will absolutely, right now, pray you find that courage, too! Thank you for the inspirational comment!
Wow. I had a small shop in MIdlothian Va – POSH – and we bought from you when you did the personalized stationery. WE LOVED IT!!! Then we opened a bigger store and my life was nothing but work, work, work. We probably averaged $1.82 an hour with the little we paid ourselves.
We closed the store, and planned to go on the road around town – a sort of caravan pop up store. To have some more time at home. I also was going to start a blog about 50 somethings having to reinvent, etc.
Then at Christmas 2012, my only son, died by suicide and that was that. No more dreams, there would be no children, no weddings, no grandchildren. There was no business to speak of by that time. My little brother had died suddenly 18 months before. Hell, my dog died, 4 months later.
After about 2 years of feeling obligated to live for others, I started to get some motivation back and some glimmer of hope for something/anything – trying to find my forward without my boy.
Fast forward 5 years…still not sure of my purpose here, I am getting ready to tell my story on another blog – THIS WEEK – and then begin my blog finally. (It will be very different than originally planned.) Then I read this. (I’ve rooted for you for years, and didn’t know exactly what was going on behind the scenes. Began buying your day designers, and loving them.)
So while I’m not sure where God’s grace figures into this for me – I struggle with feeling abandoned – I will plod along. Thank you for your inspirational story and the nudging to sit and write what I am sure will be very hard to put on paper.
I’m at a loss for what to say as nothing seems “right” but your comment brought me to tears and I feel compelled to say something. You comments have touched my heart. I will hug my boy tighter tonight and say prayers for you and your family. Hugs.
Hi Gray,
I have tears in my eyes reading your story- I’m so sorry for all the loss you have experienced. So much for one heart to bear! I just wanted to send you a little encouragement – you HAVE.NOT been abandoned! God is creating a beautiful next chapter for you…sometimes it just takes time before He reveals it to you. It’s o.k. to plod, but keep that little bit of hope in your heart that you are moving forward towards something good. I have been in dark valleys for long periods of time, and wondered many times where God was, and why the hell He wasn’t “helping me”. Now I try to thank Him each day for all the good things in my life that I don’t know about. It gives me a sense of excitement, curiousity and gratitude…looking forward to what He has planned for me.
I recently read this quote from Victoria Erickson: “Your story isn’t calm. The road has been chaotic at times, fille with detours and rain and loss so sudden, and soon. Sometimes the bliss was so elevated your heart could hardly hold it. Sometimes it was maddening to have, and then to lose. You learn soon enough that it hardly ever goes as planned- gentle, easy and smooth. But that my friend, is what makes you fascinating. You have something to tell. Something you’ve walked through. Something wild. Something courageous. Something true. You’re made of stories within stories within even more stories. Those quiet depths of you.”
I hope this gives you a little encouragement! 🙂
Elle W.
You are an amazing woman!! I’m much older than you and reading about your businesses and the success you have had and all the rest that comes with it BUT BUT BUT you don’t quit, God is using you!! Love that you rely on God! How exciting for your future! I didn’t know you weren’t involved with DD anymore, love that product!! Your post was very encouraging and REAL!! Thanks for sharing!
Thank you for sharing your story Whitney. It is always so inspiring and comforting to listen to (and read!) you.
Ever since I did your ‘The Well-Designed Year Life Planning System’ in 2016, my life has been focused on my core values and that has led me to turn my life upside down and inside out! I just wanted to THANK YOU. You’ve been instrumental in helping me find out what truly matters most to me and I’m amazed that 2 (the hardest ones! Wasn’t sure that they would be possible) out of 3 (difficult too!) of my Big Goals have been realized already! It’s been a crazy ride! My life is finally just beginning to settle down a bit. There were detours and change of direction and major stress and upheaval and a reluctant husband as well. But in the scheme of things, he’s been great.
I love my Day Designer and it inspires me and comforts me as ‘my partner’ in helping me live My Well Designed Life (that includes changes-by-design).
So, THANK YOU! THANK YOU! THANK YOU!
I, too, have followed and adired you since 2010. I so appreciate your transparency. I struggle with comparison (the thief of joy) and the longing to do/be more than a mommy. Thank you for this post. You are amazing and I know the next venture will be better than the last. Can’t wait to cheer you on from the sidelines.
Excuse the typos. I’m replying on my phone while rocking my baby to sleep. Unfortunately, they’re not because I’ve had a glass of wine. 😉
Thank you Whitney for sharing your story with us, and your willingness to be open and vulnerable. As a small business owner, I know there are SO MANY ups & downs, and days when I feel like I’m moving in reverse, heading further away from my dreams & goals. Growing up I was taught making mistakes = failure, and so mistakes and failing have had such a negative connotation for me – something to be avoided at all costs. But I am (slowly) learning that is not the truth. For in each experience, there is something to be learned, a place to grow, and often times, redemption and an opportunity for God to lavish his grace & blessing upon us to show us how much He loves us. Please keep sharing your story with us!
Elle W.