Kendall, looking forward to hearing all of your stories today. Being a business owner can be really hard sometimes. It’s rewarding, but most business owners we’ve spoken sometimes think about what it would have been like to have had a regular job instead. Have you ever wondered that yourself? Maybe you can talk to us about a time when you felt this way?
I think it’s very normal for small business owners and creatives to jump back and forth often between fulfillment, contentment, joy in their work, and overall happiness with their decision to work for themselves; and burnout, lack of stability, stress, and the loss of feeling like you’re part of a definitive workplace culture.
Early on I definitely didn’t always feel “happy” as a business owner. It was hard to explain to family and friends my decision to be self-employed, and I didn’t always feel like people took me seriously or legitimized my work. I also wasn’t financially stable as a business owner until very recently, about 5 years in, and so the pressure to return to the workplace was always, always looming.
I was newly married the year I decided to start a business and work for myself full time. There was regular volatility in my house about money issues, and I felt really guilty and selfish at times for being an entrepreneur when it affected our ability to do things like have a solid savings account, pay our bills on time, and establish retirement savings.
What kept me going though, and towards that vision of “happiness” was that I remember waking up the first Monday of quitting my last job and realizing I didn’t have anywhere to be that day. I didn’t have anyone to report to, or anywhere to go. It was such a freeing feeling, that I almost felt like after years of doing everything I was supposed to -going to college, getting a degree, working in a corporate salaried job, having all of the structures of stability – I felt like it was one of the most human days of my life. The pressure to make money was felt almost immediately, but it filled me with so much drive and creative energy to know that I, and I alone had to make my own money.
When I booked my first clients, I loved the flexibility of knowing that once I had completed my tasks and to-do list for the day, I was done. I could go on a hike, cook, take advantage of a sunny day, visit with friends, go walk aimlessly around a bookstore. I felt really childlike, as of I was doing something wrong, having fun and seeking out pleasurable activities on a Monday of all days felt so counterculture. I realize that not having Sunday Scaries is it’s own form of happiness, and peace. I realize that even if I sometimes crave a regular salary, I know it’s much more motivating and exciting for me to develop a service, sell it, make money from it, and create a good experience and strong connection with my clients.
I started my business in my late 20’s and am now in my 30’s, and so blindly running a business without the goal of financial stability was never going to work for my situation. I had, and have to be profitable because I share an equal responsibility in our household. Even if my contributions are less predictable than my husband’s regular weekly paychecks for wage work, we require both incomes to support our family.
Now, five years in I can definitely say that I experience a lot of happiness in my work situation. I think most of that comes from having flexibility in my days and weeks, lots of autonomy and agency, working seasonally with an intense summer season but then having this beautiful space of rest for the entire winter to focus on my family and slower rhythms. And continuing to grow my profits also is a source of fulfillment and contentedness – because I realize now that not only am I offering a valuable service but that I don’t feel like I need to beg people to hire me, there are people who are happy and grateful to pay for my services at a life sustaining rate of income. I also finally figured out the balance and boundaries of work. I think it takes a lot for a creative person to say to themselves “I’m allowed to have work hours, and non-work hours. I’m allowed to take 72 hours to respond to a non-essential email. I’m allowed to minimize texts related to work and limit my evening office hours”. Once I figured that balance out, I definitely noticed more happiness when I showed up to work.
Where I also recognize happiness show up most days is the awareness that I am a mother to young babies (ages 1 and 3) and I have the enormous privilege to be home with them and raise them during their childhood years. Basically all full-time, salaried or wage work, and any work other than entrepreneurism and small business ownership requires you to outsource the care of your children in their pre-education years, and that wasn’t a life I was interested in. I wanted to do everything I could to feel like I could earn money through something creative from home.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
My name is Kendall Rose, and I am 33 years old. I started my business as a wedding planner and event designer, The Revel Rose in November 2017. I grew up in Metro Detroit, and in my mid-20’s moved to Northern Michigan for a job with the National Park Service. I was an Outdoor Recreation Planner focused on environmental and conservation projects on public lands at the time and was convinced that I had found my dream career and dream job. It was pretty perfect and made me feel like I had made all the right decisions to bring me to this point where my degrees, job experience, internships, and experience all made sense.
In 2016 following the federal election, the grant program that funded my position was paused, and my boss who I really loved and respected prepared me for the fact that instead of moving into a permanent position in the spring, I would likely not have a funded position after May. All of our projects were put on hold, and the atmosphere in our department became truly sad and demoralized. When we realized my position funding had been cut for the year and I wouldn’t be able to renew my contract, my boss helped me find a job at a non-profit in Traverse City, Northern Michigan. I didn’t last 3 months. I hated it and felt just really personally victimized by the decisions of the administration at that time and my unlucky timing. I was pretty depressed that summer and in the midst of it, saw a job ad for seasonal weekend help at an historic farm catering weddings and events. I felt called back to the service industry because honestly that was a place that always felt like a comfortable and safe landing place when my “career’ plans fell through.
I started falling more in love with my work on the weekends than with my day job. We were staffing these gorgeous, outdoor, farm to table dinners, weddings, and events in one of the most gorgeous parts of the region, and I was loving the physicality of the labor along with the purposefulness. It felt great to not be sitting at a computer or a cubicle, and sharing in these communal celebrations and moments where people gathered together and were really, really happy.
At the end of the summer I quit my job at the non-profit and decided I really wanted to be in the events and hospitality world. For some reason, without having any experience I felt confident that I could be a wedding planner. It was driven by this sense maybe that I had a good project management background, and a wedding was essentially a project – with a budget, scope of work, timeline, and hired vendors that needed to be managed. I never thought that the wedding industry was super interesting or something I’d be drawn to, but on those weekends on the farm I realized that events were really just a collective and collaboration between several creatives and small business owners. There were farmers who grew the food, local chefs who prepared it, farmer florists, bakers, musicians, photographers, dress designers, stylists. It was like being on a movie set. I had always sort of wanted to be in the film industry but Michigan isn’t really set up for that any more, and yet I had this feeling of production and execution on event days that was intoxicating.
I am so proud that I gave this a shot, because The Revel Rose took off right away. My first large client booking came only 3 months after I started the business on a referral from another vendor in the industry. I was hired for full service planning, which in my industry is the most responsibility you can have for a client and their wedding. It involved everything from booking a venue and vendors to planning multiple events related to the wedding, to designing the entire evening, and then executing a week of set up and preparations. I learned so much from that wedding – most of it positive, and some of it difficult. I threw my back out two days before the wedding from moving some large items on site and realized this job was much more physical than I planned on. We work 12,15,18 hour days as wedding planners, sometimes walking up to 30,000 steps on a single afternoon and without the proper care and staffing, your body can take such a hit. I learned I would need to limit my work scope in some ways, hire additional help in others, and most importantly.
The Revel Rose was definitely an alter-ego hidden inside of my spirit that I had long ago buried. I was a creative kid who painted, drew, wrote plays, wrote poetry, and did pottery. I loved all of that until it came time to go to college and I failed art school and convinced myself that to be important, I had to do certain things and not others. I lost pretty much all touch with my creative side for about a decade. And yet I now realize that a lot of what being a wedding planner is were these innate qualities I always had and was meant to share with others; I get really excited about throwing a good party, creating a vibe, finding all of the best people to make a vision come together, and giving people an experience that doesn’t feel like anything but them.
I take a lot of pride in the fact that as a wedding planner, I have found and worked with new and upcoming creatives and given them some of their first opportunities at paid work. It’s a wonderful feeling when couples and clients say “thanks for introducing us to this person, they were the best fit we could have asked for”. I take a lot of pride in the fact that as a designer, I am working more towards a feeling than a look. My work has never been published in a blog or a magazine but that’s okay because I think they are more so supposed to be experienced than just photographed. While it’s a worthwhile pursuit as a creative to be published and recognized for design work, events are ephemeral, living organisms and focusing on perfection is unrealistic and frustrating for everyone. I love knowing that throughout the past five years I’ve heard “this is the most beautiful wedding we have ever been to” enough times to be more confident in my skillset and the uniqueness of what I provide.
And most importantly. I am very grateful and thankful for my couples. My job is to help them have more fun planning their wedding. Simplify the process where and when I can. Build trust so that they can leave me with the task of managing up to 50 other business owners who they have paid to give them an incredible experience. I have a side job as a counselor, as a confidant, and as someone who can help them navigate the really difficult aspects of wedding planning such as having boundary issues with a family member, respecting each others wishes and different ideas, and dealing with life’s hardships such as a divorce, death in the family, or loss of friendship which sometimes occur during the wedding planning process.
What’s a lesson you had to unlearn and what’s the backstory?
Within my first year of being a wedding planner, I ran into conflict with a couple. I really didn’t feel like they had hired me with the intention of being in a partnership, and it was clear they didn’t trust my insight, experience, recommendations, or opinions – which meant a stalemate on important decisions related to their upcoming wedding. As we got closer to their wedding, our relationship became contentious and disrespectful, and I did something very unusual in this industry and ended our contract, AKA broke up with my clients. They of course, were upset and angry with me, and we began a lengthy exchange in which they sought monetary compensation, and I withheld it citing that I had fulfilled my workscope up until the point of our contract end. They mentioned suing me, so I had to invest in a lawyer in case that happened.
I never heard from the couple again, until 8 months later when I was on my way to a very important, invite only vendor showcase. I got a notification in my email that I had been left a 1 star review on my business site and it was paragraphs upon paragraphs long. I was too upset to read it, and it knocked the wind out of my sails for the event I was at. I felt so defeated and exposed. There was no way to remove the review and when I finally got up the courage a few days later to read it, it’s permanence made me feel like I might need to end my business. I couldn’t imagine living with those words being public and still getting clients to hire me. My friend, who is a PR consultant helped me try to craft a measured response, but unfortunately I didn’t take her advice and left a long, impassioned response driven by anger and embarrassment.
There is this established thought in the wedding industry that you HAVE to work with difficult clients even if the relationship is suffering and push through. That you HAVE to financially compensate a disgruntled client even if they were the ones to breach the terms of your contract in order to prevent them from leaving you a bad review. That you HAVE to have a perfect, 5 star record of reviews in order to be a successful business owner. These were all assumptions and lessons I had to unlearn that year and through that experience. And I think that really set me apart as a business owner because I have done it several more times, and I now sort of have this reputation in this industry of being the one to call when a business owner wants to write better contract terms, or break up with a client, or deal with a bad review.
Lesson one: I do not believe it’s helpful for anyone to be in a bad working relationship, and I think contract-based creatives need to write themselves a way out in their contracts well ahead of any forseen challenges. Clients deserve to work with people who enjoy them and have their best interests at heart, and contract workers deserve healthy working relationships and decent boundaries.
Lesson two: I do not believe it is always on the business owner to offer monetary compensation to a client if the contract dissolves. I think the financial responsibility lies on the party that breached the contract. Since that time, occasionally I breach the contract by determining we are a bad fit after we begin working together, and I have refunded the client their retainer payment. Occasionally, they breach the contract by for example, reducing my agreed upon paid contract hours or changing a date or location of their wedding and I am unable to accommodate it, and therefore I see them as being responsible for the breach of contract.
Lesson three: It took one amazing phone call for me to realize that any review besides 5 star ones aren’t anything to be ashamed of. I was on the phone with a potential client, a woman in her 40’s who was super professional and I really wanted the job. She said “So about that 1 star review” and my heart sank. I thought this was about to be the end of our phone call. Then she just started laughing and said the client sounded like a total jackass and she thought I handled it so well. She then asked when we could begin working together. I booked a job because of a poor review and my response to it, I couldn’t believe it. Potential clients NEED to see how you respond to criticism, stress, conflict, and problems. No business owner is perfect, and no business is always going to be 100%. I think clients learn a lot about who you are as a person when you can address conflict and own up to it. I still wish I had taken some more time to chill out before I left my response, but in hindsight I am so glad I didn’t exchange money with this person for the hope that they wouldn’t drag me under the bus in a public review. I’d rather keep the money I earned and suffer the consequences of a review, and more importantly I am glad to continue learning about the types of client relationships I don’t want while continuing to pursue the ones I do.
Is there something you think non-creatives will struggle to understand about your journey as a creative?
Even though I’m not really comfortable sharing this, I definitely hope at least one person can read it and feel some sense of hope or feel seen.
I have severe mental health illnesses, and I wasn’t aware of them or diagnosed until I was 31. I am Bipolar I, ADHD, and struggle with OCD and Body Repetitive Behaviors Disorder (BRPD). I was diagnosed with these following a very routine therapy appointment in which my therapist asked if I would be open to a psychiatric evaluation. I went into that 5 hour evaluation blindly and came out with these terms, and a feeling like I would never see myself the same again.
It has taken two years to finally come to terms with the fact that these diagnoses are a part of me, and in some ways they are me. Even though I spent some time wishing and wanting and trying to detach myself from them, I think a lot of peace came from realizing that the structure of my brain as a result of these illnesses creates a sort of beautiful arrangement that actually makes me a good entrepreneur, business owner, and creative.
The lack of impulse control that is characteristic of Bipolar disorders likely helped push me to leave uncomfortable work situations and propelled me to be a bit more brave with what I’ve tried over the years. Regular phases of mania, while really frustrating, isolating, and exhausting at times definitely help propel me creatively, and being self employed allows me to work in shifts that are more natural to my internal rhythms. If I have a set of interesting ideas I can act on them at any time of the day, be it midnight or 6 AM, and I don’t have an elaborate system of wall clock based time I need to adhere to. Working for myself has allowed me to structure my days and weeks more holistically than if I worked for a company. I can focus on activities that are grounding and self care oriented. If I am in a manic state, I can collaborate on several ideas at once with several people and feed off of that social energy. Having ADHD has meant that I can respond really quickly to ideas and action items that interest me, and I can keep using that as the litmus test to bring me closer to what I really, really like doing while removing work activities that I always put off. I have a great of way of reflecting on my work by saying “do more of the thing that you hate being distracted from”.
What was painful was realizing that having mental illnesses might have hindered my ability to function well in a traditional academic setting and at my first corporate job where I stayed for 3 years, even though I was miserable and everything in my body seemed to react to that misery. I told myself if I just became more disciplined and focused, I could prove myself in this environment. I spent a lot of my 20’s wondering why everyone around me and my friends seemed to be able to do very normal things like get dressed and ready for the day, show up to work on time, knock out some tasks on a computer, take a lunch break, knock out some more tasks, go home, and do it all again the next day. I felt like an animal in a zoo but I didn’t really know what alternatives there were to a cubicle office in the 2000’s.
I would love for people struggling with mental health to know that a proper diagnosis can be really affirming. That it can help you make sense of who and what you are so that you can find the environment you belong in. If we go back to the animal in the zoo analogy, it’s all about being in the right ecosystem for your particular set of characteristics and needs – and being a “creative” isn’t an impairment. Creatives add a lot of value to the human experience and instead of the creative/mental illness connection being a trope, it should be a relationship that is given more attention earlier in a person’s life, and with some more grace around it.
To follow up with the diagnosis bit, treatment is essential. I can say with certainty that I would not be able to do work I am proud of without medication. It’s very hard to accept mental health diagnoses, and it’s even harder to begin taking medication I think. It took me 1.5 years after my diagnosis to accept that therapeutic medication wasn’t poison, and that long term it would mean I could hold onto the things I really treasure in my life; my family, my kids, my health, my work, and my relationships. One of my favorite people early on in my Instagram years was Beth Kirby, the super successful writer and blogger behind the account Local Milk. When I remembered that she had shared her Bipolar I diagnosis openly with people who read her work, I felt like someone had just turned a light on at their house, and I was walking towards it on a very dark night. Just knowing one other person out there knows what it’s like to live inside your brain is really comforting.
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Lindsey Makuwatsine