midnight hustling with kendi of kendi everyday

When it comes to questions about designing a life with intention, I often get asked about how to launch a small business dream while juggling an un-fulfilling day job. For most people, the answer is to grow the business on the side while working a 9-5 position until the dream business is profitable enough to take full-time. Niki coined the term “Midnight Hustlers” for this band of entrepreneurs growing their business late at night, early in the morning, and on the weekends.

Though it might be argued that Jess LC is my own version of a “day job” since it isn’t directly related to my purpose (helping others design a life with intention), I wanted to share the experiences of my Midnight Hustler friends who are now pursuing their vocations full-time after working for large companies. This interview series is designed to share their personal experiences with jumping off the corporate ship and building a life raft to their next venture.

I know that many Midnight Hustlers feel isolated while working hard during their free time alone, and hopefully these stories will be inspiring and helpful for those who are burning the Midnight oil or are thinking about doing so in the future. Each Hustler had her own method to create the life she wanted and I hope that this series highlights how many different ways there are to go about accomplishing your dreams.

Our first Midnight Hustler is Kendi, of KendiEveryday. As you know, we’ve worked together on the recent Diversey lookbook, and I’ve been constantly impressed by her desire to be her own boss in a community where self-employment is rare.


When you first got really serious about launching your blog full-time and were still working your day job, what fears did you have about making the shift? How did you overcome those fears?

My situation is unique as I help my husband with his photography business and I run a style blog. Although I don’t consider Kendi Everyday a “company”, I did decide to take it
full time. I was already working basically full time on my blog, full time at my day job, and weekends with my husband on photography so really more than anything I needed a break from one. And my blog or my husband’s business was not going to be it. So had to make a choice, stay put or jump in.

The biggest fear I had for going full-time was/is failure. I say is because while I conquer one fear of failure, another one creeps right on in. I have a feeling this is a constant in
owning your own business. Besides public speaking, I’m pretty sure that failure is on everyone’s top list of fears so I know I’m not alone out there. But my fear of failure came
out in a form of question. An innocent question at that. It started when I wanted to quit my job and that’s when the fear starting rolling in in the form of “What If?”

“What if” became my frenemy. I thought that I was doing some good by playing devil’s advocate and covering all of my bases of the unknown. I would ask my husband “What if I fail? What if it doesn’t work? What if blah blah blah, insert anxious filled question here?” all of the time. “What if” became my motto for a few weeks, with me dreaming up a new terrible scenario in my head and asking my husband to rate the possibility of it actually happening. (He never answered my ridiculous requests). “What if” became my crutch, my excuse for not doing anything but whine. A swan song of modern times.  After a few weeks of this, I realized that the only way to stop asking these draining questions was to quit my job and take the leap into the unknown. So I stopped questioning, faced my fear of what if and I quit.  Once my three weeks was turned in, I could no longer ask the “What If” scenarios because I was now living it. My reality was now open up to everything that I’d been dreaming up to fear. And you know what? Not one of those scenarios has come true thus far.

I feared the unknown of quitting my job, even though I had my ducks in a row, even though I knew it was time. I had created a fear for what I needed to do and instead I hid behind two simple words — what if. But the minute I stopped asking “What If” in a pitiful voice of fear and asking it in a strong voice of reason, my situation changed. No longer did I ask “What if I fail?” I asked “What if I don’t try? What if I don’t step out there?” And by simply changing the question, I was able to see that no matter what happened in my dark terrible scenarios that I dreamt up, nothing was as bad as what if I didn’t ever try. When you think about it, failure isn’t a bad thing to live with. I’ve failed many times and plan to again in my life. But I’d rather remember the times I tried and failed than regret the times I never tried.

How did you structure your day balancing both your job and your growing blog?

My day job was just that — a day job.  It was my Monday through Friday commitment that allowed me to continue my work on my blog, financially speaking. Once I realized that I didn’t want to spend my life’s work building someone else’s company, I took my job just as a path that would take me from where I was to where I wanted to be. I worked hard at my job while I was there and tried my best to leave it there when I left for the day. My second job (my blog) started the minute I left work. My husband and I would take outfit photos right after work (we still do) and in between dinner, cleaning and being a wife I’d work about 4 hours a night on the blog, editing photos, writing posts, answering emails. During the day I’d answer a few emails and questions that I could, but the majority of work was done at home after hours.

The balance is still being figured out. I’m a tiny bit of a type a personality so I can be prone to work too long, too hard. I struggle with balance a lot like how do I watch a movie instead of blogging or writing or some other random activity that pertains to my blog? I struggle with letting my new job be my only full time job, instead of functioning at the speed I was  functioning at for almost a year. So that is my next challenge, to realize that my full time job is now my only job.

Did this require any sacrifices?

Of course it did! But in a way our life in this small town was set up this way from the beginning, so it wasn’t a cut and dry sacrifice. Where I live it is hard to find young people to hang out with. And even if I did, we’d have to travel 45 minutes to have anywhere decent to go hang out. So with close friends nearby out of the picture, my husband and I were able to both launch a business or a blog in our spare time. He launched a wedding photography business and I my blog. (I realize this sounds pathetic and lonely but no worries we have close friends that don’t live too far away) One day when we pick up and move from this small retirement community and we most definitely settle in an area with young blood, we will have to figure out a balance between social life and work. Which is a balance I’m excited about.

Of course along the way there were other nominal sacrifices, we gave up cable, we don’t eat out very often in order to save for Bryan’s photography business, etc. But when I think about the short term return versus the long term return I don’t mind these types of sacrifices. Besides, no one ever built a company by watching 8 hours of Gilmore Girls marathon.

How did you select your quit date and how did your company respond to the decision?

I hate to admit this but I quit my job on a whim and about a month earlier than my husband and I had planned. We knew that it had been coming for a while, so there was a definite plan for when I would quit. But the weekend before, it became overwhelmingly clear that I was supposed to quit, so the next day I went in and I let my company know. The company I worked for responded okay, as they didn’t quite understand my new ventures. Only a few people at my work even knew about my blog, so explaining to them in full what I would be doing would have taken me a lot longer to explain, starting with a “what is a blog” lesson. It was hard to leave my position, my salary, my security but I knew in my heart it was time.

Were they surprised? Were they supportive?

I’m not sure if anyone was surprised. I think a few people were but the ones closest to me were not. And on the flip side not extremely supportive.  Of course I knew this going into it, however. I knew that my support would not come from coworkers but from my core group of family, friends and my biggest support from my husband.

What is the best piece of advice you wish you had before you started your midnight hustling to have a smoother transition to self-employment?

Listen to yourself and no one else. No one else knows what is right for life but you. Sure people give advice (some give great advice, others not so much) but you are in control of your life and you are in control of what advice you take. I had a few naysayers along the way and probably still do, but you know what? Those people don’t get to deal with my mistakes and they don’t get to celebrate my success. I had to figure that out over the past year. If you know something is right for you, go with it and go full force. You are the only one who can make it happen.

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  1. Jill

    love this new series! I’m such a huge fan of Kendi and can’t wait to see all the new adventures that life has in store for her!

  2. Niki

    Yay! I love that you’re spotlighting my fellow “Midnight Hustlers” – we truly are a class of dynamic people! 😉

  3. It is really inspiring to read about Kendi’s experience. Way to go, Kendi! This is a fantastic new series, Jess; thanks so much for curating it. 🙂

  4. Woot for all the Midnight Hustlers! Even though I’d just started reading Kendi’s blog when she announced her change, I was so excited for her, because I TOTALLY understand spending hours and hours somewhere that is uninspiring and unfullfilling. It’s bad for the soul! I too am excited to see where this new adventure takes her.

  5. Lauren

    Really looking forward to reading this series of blog posts, since this is exactly where I find myself! I’m at the crossroads of figuring out how to launch my own part-time style business, so this was great to read, especially from a woman who I admire so much!

  6. Annie

    I’m thinking this is going to be an awesome series… I like that Kendi’s answers can even be applied to just achieving balance in life, even if some of your readers don’t necessarily qualify as “midnight hustlers.” 🙂 Looking forward to reading more!

  7. Cathy

    Oooooh! I love this new series! It’s so interesting reading how people (especially women) got their start as well as what they’ve learned along the way.

  8. I love this! You have show cased people already living their intentions so this is wonderful for those of us who are in the middle or at the very least thinking of following the life we designed for ourselves. Thank You!

  9. Katie

    thanks for sharing, kendi. i love your blog and after reading this i think i love it even more – if that’s possible! such great words of advice:
    “I had a few naysayers along the way and probably still do, but you know what? Those people don’t get to deal with my mistakes and they don’t get to celebrate my success. I had to figure that out over the past year. If you know something is right for you, go with it and go full force. You are the only one who can make it happen.”


  10. Jenny

    I love this new series. I recently just became a midnight hustler. I’m a paralegal by day and I just recently started a design/diy blog. I love to see that other people can quit a job that is unfulfilling and follow their dreams. It gives me hope 🙂

  11. Kirsten

    Thank you so much for this post. That’s the perfect term – “Midnight Hustlers”. Love it. And you’re right – it can be so lonely. But the prospect of building something is so invigorating. It’s blogs like this that keep the energy going.

  12. Flavia

    I am very excited about this new series. Loved hearing about Kendi’s path to success – very inspiring!

  13. Gina

    I love this series! I just quit my day job 2 weeks ago and struggled/am still struggling with the “what if?” factor.

    I love how Kendi says “what if I didn’t try?” That is something I am trying to focus on. The other thing I focus on is “What if I succeed?” Thinking about and focusing on success is far more useful that dwelling on the idea of failure.

  14. Lani

    So inspiring and just what I needed to read today! Cant wait for more…

  15. Alexa

    I love this interview. It’s a great idea to focus on the midnight hustlers – and it’s definitely inspiring me to become one too. Kudos to both Jess and Kendi!

  16. kelsey

    Very inspiring, Kendi! I am currently in an un-fulfilling day job and hope to be full-time on my blog in a year or so. Thank you for your insights!

  17. lola

    what are you going to do when this whole “blogging boom” collapses?

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