five years


On August 16th, 2007 I moved into a tiny Chicago studio. My parents helped me U-Haul my belongings from Michigan to my new Lakeview address.

All of the boxes completely covered the floor space in the new apartment. And when I realized that the over-sized closet wasn’t large enough to fit my bed and act as a mini bedroom, I cried.

I really didn’t want to work, live, and sleep within the same four walls. 

Fortunately, I put my belongings away and discovered that though the studio apartment was not large, it was enough.

For weeks I struggled to find a rhythm to my business. Unlike the rest of my peers and boyfriend who moved to Chicago at the same time (we all graduated that May, four months earlier), I had no “start date,” “salary,” or “boss” to look to for answers and guidance.

I had decided to take my part-time jewelry business, which I began when I was fifteen, to the next level by making it my full-time gig. Was the business really ready to support me and my bills? Not at all. I just knew that I was meant to help people “make under” their lives and the jewelry gig was the safest way for me to stay true to that intention.

Had I gotten a day job like my friends I easily would have climbed the corporate ladder. My type-A personality and insistence on pleasing people would have distracted me from my ultimate goal: to help people with a book, tv show, or any other way that I could spread my message of simplifying life.

Over time, I fell into my groove with the business. And though I had my share of anxiety attacks, I saw myself persevere and push through an unending sea of challenges. I saw myself become a stronger person.

At first I did everything for the business myself from designing the jewelry, to making it, and selling it. I worked alone each day and listened to books on tape to keep myself mentally occupied. After the first five months I got my jewelry into 15 stores in Chicago and Michigan.

In order to make friends in the city since I worked alone, I decided to train for a marathon with Team in Training. In the winter. Thankfully, despite the freezing temperatures, I did make a friend.

Each week I knew I needed to sell $1000 worth of jewelry in order to pay my bills. Some weeks it happened easily, others it took a while, once it happened at 5:30 on a Friday. I’ll never forget that Friday.

By January of 2008 I took on my first part-time assistant. I met her while working one day a week at one of the boutiques I sold to. A young customer walked in who looked like she might be a college art student who knew how to make jewelry. Miraculously, I was right.

I also took on interns and sales reps. The reps took my business from 15 accounts to over 100 in 12 months.

They even helped me get a small space at a trade show in LA. Though I had accomplished seemingly so much, I cried that night after the show in my hotel room alone. I didn’t like the wholesale and trade show part of the business. It wasn’t for me.

But fortunately all along the way, though there were many tight moments here and there, I was able to pay my bills in full each month.

Once the recession hit late in 2008, I saw the wholesale market shrink considerably. But rather than try to find new reps or seek more wholesale I decided to stick to keeping things in-house. It made me happier. I also started Makeunder My Life (this blog) on January 19th, 2009 as a place to journal my journey to design a life with intention. I didn’t expect anyone to read it, I just wanted to eventually take the content and compile it into that book proposal that I had in mind.

Though it had taken all my attention and energy the first year and a half to make the business support my life, I didn’t want to end up with a booming business and never take the time to go after my purpose. The blog was my first step towards working my purpose into my career.

Meanwhile, I was living with my college boyfriend in a tiny studio apartment across the street from my tiny studio apartment/corporate headquarters. Our place was so small that we could vacuum the whole place using just one outlet. The only door we had in the whole apartment was on the bathroom. So if we got into a fight and I wanted to pout, I had to put my head in a pillow on the bed… which was just two and a half feet from the couch and four feet from the kitchen.

We lived in that studio apartment for Two. Full. Years.

Oh, and remember that blog that I started to create a book proposal? Because I started to market my jewelry online instead of seeking more wholesale accounts, it started to get readers. Those who clicked from my ad on another blog to my site would then click on my blog link and read along.

Though I honestly never saw that coming, I immediately embraced the opportunity to start helping people right where I was each day. I realized I didn’t need a book or book tour to meet women and help them with their lives. I could do it online.

From that point forward my blog became equally important to me as my business, which paid the bills.

By September of 2009, my boyfriend and I were ready to bust out of that apartment. We found an amazing two bedroom apartment across the street. It had doors and rooms! 

I honestly felt like we had won the lottery.

But just a few months into our shared lease, we realized that we were at different stages in our lives, possibly looking for different futures.

For six months we didn’t know whether we were going to stay together or need time apart.

Eventually by the following Labor Day, we decided we needed time apart in order to know what was truly best for us. But since we shared the lease, we decided to stay together as a couple and live out the lease. Once the lease ended we agreed to break up.

It was one of the hardest summers of my life. In order to be peaceful and loving during that time required more strength and grace than I had ever experienced. I spent each day praying and deepening my spirituality. Though I had learned to rely on my spirituality from the business’ constant uncertainty, this situation took it to a whole new level.

On the business front I decided to re-brand my company. I wanted my brand to reflect my new design perspective and products. I overhauled the logo, site, products, and marketing. Though the new look was beautiful and worth every penny, it didn’t land me on Oprah.

But there is a good side story to Oprah: at one point early in the first few years an Oprah producer lost an earring of mine and needed a new one. I almost fell off the chair, and rushed to give her a replacement. My mom thought my shaking, due to my excitement and a poorly timed energy drink, were going get me hit by a car on the way there. Thankfully, that did not happen. I gave her the earring and she offered me tickets to a show. I selected the Sex and the City movie preview and landed on their b-roll footage walking into the theatre! Later, I was also asked to do a trunk show at the studio in a green room. So freaking cool.

By the time September 1st, 2010 rolled around I was out of my mind excited to decorate my new apartment. After living with a man I wanted some pink in my life! Within 24 hours of living in my new apartment (a one bedroom apartment in the same building) it was fully decorated.

While we were going through the break-up process that summer, I had used the design of the new space to help me find happiness and opportunity during something so heartbreaking.

My first two months as a single girl were fun and challenging. Deciding to stick with the same nice building that I lived in meant that I increased my rent by 50% from the year before. But I knew deep down that I was not meant to suffer because our relationship ended. I didn’t know why it happened in a cosmic sense, but I trusted that I was meant to keep moving forward and thriving.

Two months later I went to a friend’s birthday party. It was just like any other night. While I was there a guy approached me who seemed funny and kind. I asked him to be my “guy friend” and get brunch with me the following morning. Since he was new to the city and also looking to make new friends, he agreed.

That guy happens to be named Mr. Lively. Over the next two weeks we hung out almost daily and he made me laugh to the point of tears almost every time. About a week later I started wondering why he didn’t text me goodnight… All the while I still considered him just “a friend.”

By the time the two week mark hit he kindly visited me at a holiday trunk show I was at for my company. While I deeply appreciated his presence and support at my event, I did not appreciate him talking to the cute girl, named Jessica, at the booth next to mine.

At that point I couldn’t ignore my feelings any longer. I really liked this Mr. Lively. A lot.

From that point on we were inseparable.

Because of my past relationship ending, I spent a lot of time talking about what our intentions are for our lives and futures with Mr. Lively right from the get-go. Luckily for me, he is also a planner and was game for the discussions.

By this point I was getting eager to change things up with my business as well. I decided to try designing handbags, my favorite wardrobe staple. It took me several months to find the right contractor, but I did get to make the bags swirling around in my head.

They were a huge success and they opened me up to the idea that I could design a variety of lifestyle goods. Not just bags and jewelry. I quickly set forth to design anything and everything I could think up. I went from designing two collections a year to eight.

People loved the new selection and the company grew. It was a really fun time, though filled with bumps and steep learning curves.

Eventually my tech-loving dad suggested I design an iPad cover. So I tried my hand at that and quickly outgrew my first manufacturer. It was hard, but eventually I found a new company to work with that could accommodate my inventory needs. But again, I had another steep learning curve to face.

Meanwhile on the blog front I had been getting more and more requests for business consultations. I was happy to take them up on their offers and help them design their businesses with intention. It felt amazing to do what I love the most, helping people, as a career.

By early this year (2012), I decided it would be nice to take the consulting to the next level by offering a workshop for men and women who had similar intentional business goals. I shared this in a small paragraph on my blog one day and I got an email shortly after. The person writing me offered to help plan the workshops and make them happen.

What had just been an idle “wouldn’t it be nice if” immediately became priority number one.

I spent the first half of this year creating the workshop with this new-found friend and held events in Chicago, Washington DC, and New York. We had hoped to do even more this year, but juggling the accessory business, consulting, workshops, blog, and my life became too much to handle.

This year Mr. Lively and I had also grown considerably. On May 30th he asked me to be his wife. Four days later after a lot of wedding talk, we decided to elope to Paris.

The summer was a whirlwind of business juggling and trip planning. I savor every minute of the past several months, but I had plenty of anxiousness while trying to juggle everything on my plate.

Yet once we landed in France, it was time to relax. We spent nine wonderful days exploring Paris.

And somewhere during that trip August 16th, 2012 passed quietly. The five year anniversary of my life in Chicago. It is truly astounding to think of where I started this journey and where the five year mark landed me. There were more highs and lows than I would have been able to comprehend had you whispered the story to me early on.

But that’s the thing about designing a life with intention. You can do your best to seek your happiness and often you will be right. And other times you’ll find that challenges you never expected can lead to happy endings… or beginnings.



This Post Has 42 Comments

  1. Joey

    Congrats on all of your accomplishments over the past five years. It’s crazy how five years can seem to zoom by so fast, yet be jammed packed with so many life-changing events. My boyfriend and I will reach our five-year anniversary next spring, which will also be my five-year anniversary at my current job. I’m really looking forward to reflecting back on those years and seeing how much I’ve grown and plan for the next five years!

  2. Ariel

    Thank you so much for sharing your story with us! What an inspiration! I’ve only been following your blog for a couple of months, but I have learned so much. And you truly have inspired me to stop sitting around and waiting for something to happen with my life. I’m starting to feel ready to just “go for it.” Thank you.

  3. This made me cry but with joy for you and a huge respect and admiration for your tenacity and pursuit of happiness. I sincerely wish you many more happy joy-filled years to come.

  4. I loved this post. So interesting to see how things develop, regardless of how we “plan” for them to happen. I also graduated college in the spring of 2007 and have been a little nostalgic lately, but also amazed at the direction my life has taken – very different (and better!) than I expected. And the things that I thought I wanted at the time that haven’t worked out were all for the best.

  5. Great article Jess! It really made me reflect on how dramatically my life has changed in the last five years – I don’t think I even realized how much until now!

  6. Nikell

    Huge congrats on your accomplishments! You’re such an inspiration. (^_^)

  7. Giovanna

    Your are such an inspiration! I “discovered” you years ago, when your apartment was featured on Apartment Therapy and feel privileged to have been able to follow you along. Thank you for your honesty, and congratulations!

  8. Anouk

    Jess you are a true inspiration to me. You make me believe in my dream and continue the hard work. I want to have a life like yours, with highs and lows, and I am determined to have it !

  9. Lorena

    What a great story. Thanks for sharing, it was beautiful to read and very inspiring.

  10. karlita

    Oh Jess what a beautiful and at the same time hard story. Thanks for sharing the insides and processes of what we know now about you. And we can’t imagine what you will be saying about this moment in 5 more years 😉 that must be something good about life. Congratulations!

  11. B

    Hi Jess,

    I read your blog daily but have never commented before. This was a beautiful post, and I wanted to let you know how much of an inspiration you’ve been to me! You have had a lot of influence in the year or so that I’ve been reading your blog.

    Thank you!

  12. Emily

    Congratulations on such major personal and professional accomplishments Mrs. Lively! I just started reading your blog not too long ago, but you have proved to be such a great example for the blog I hope to start some day. I can’t say I dream to own my own business, but you’re exactly the type of boss that I would like to find some day! Congrats again!!

  13. Annie

    SO inspiring and helpful to read your trajectory towards success and personal fulfillment. Somehow hearing how others have pieced together their lives is always immensely reassuring and encouraging.

  14. hope

    Thank you jess for always sharing about your life and your intentions with us, even private struggles or thoughts.

    Guess we never know where we will be in 5 years. You gave me hope for what 5 years later might look like for me after i graduate :]

  15. Jowhara

    It’s inspiration in its simplest form, and goes to show that with a perseverance you can achieve all that you wish to. Reading your blog daily gives me so much hope that I too can achieve all that I want to.

    Keep up the amazing and work and I hope you go from strength to strength 🙂

  16. I LOVE your blog Jess! I’ve been following for a while now, but haven’t commented. Your reminders to slow down and enjoy life with intention, while also sharing real life struggles inspires me to hustle for my passion and keep on keepin on with the everyday. I love having insight to how bloggers got their start and this post is no exception. I hope to join you at one of your BWI events sometime soon (I’m in Milwaukee, so we’re neighbors!)

  17. Alicia

    Love your blog, thank you for being real. So happy for you and best wishes – you are an inspiration to us that read the blog!

  18. Linda

    Jess! Congrats! It made me smile to see you whizzed right by your 5 year… It’s amazing how time flies. *So glad* you took the time to reminisce and share your journey.

  19. Thank you, thank you, thank you for this post. I’m in the process of making the big decision of leaving my safe, secure (well paying) job to FINALLY go out on my own. I needed to hear this. It’s hard, it’s a pain in the butt at time… but it’s oh so worth it. I couldn’t have read this at a better time. Congrats on your accomplishments (and on your marriage!). I’m inspired by you. 🙂

  20. Jess

    Thank you all so, so, so much! I’m so happy to share my story in hopes that it helps others. It really is an honor. Thank you.

  21. Lauren

    Loved this post! Congrats on 5 years – what an adventure! Thanks for letting us following along.

  22. New reader to your site, and stumbled upon this entry and read every word. Incredibly inspiring!!! Subscribing — I have a feeling I’ll be a frequent reader. 🙂

  23. Nadene Engwell

    Hi Jess,

    What an amazing heartfelt story! You have inspired me to reach my goals and to stick at them no matter how difficult things become.

    Thanks for sharing your personal journey 😉 xxx

  24. Heidi Jo

    I just came across your site because it was linked to in the Huffington Post blog. I appreciate your message. I’ll enjoy following along on your journey.

  25. Was reading this and so many times found myself thinking, “SO SIMILAR.” I left my corporate job to do my own thing a year and some change ago. Moved in with my beau to a studio (with no doors – agh, totally get that struggle), and am now in the position where we are parting ways after a season very similar to the summer you talked about. I’m optimistic about all of the good in store and to come, and reading your honest tale made me even moreso. Thanks for sharing and for persevering! Always so worth it.

    1. It’s great to hear your story, Ashlee! Thank you for sharing. May these changes in your life continue to help you grow and expand as a person. : )

  26. This is so inspiring, Jess. I really appreciate how much detail you’ve shared and it drives home the fact that hardships and challenging times really are there to make you a stronger person and they are actually opportunities to being the best self you can possibly be! Wish you every success on your already successful journey!

    1. Thank you, FayAnn! I’m glad you appreciate the ups and the downs. I heard Oprah say that she believes that failures are the Universe’s way of pushing us towards our destiny. I kinda feel like those tough times and challenges do the same. : )

  27. It was like a movie! Truly inspiring, love the insight, everything really. Sooo many questions whirl in my head, but so thankful that you’ve always remained true to your heart no matter the challenges or disappointments you’ve always found a way with grace to intentionally be who you were always destined to be ♥

    1. I’m glad you enjoyed the story, Linda! It is a crazy ride, but I just hope it can help those who hear about it. : )

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