Letting your less-poised, imperfect human side show is an asset to connect with others and an opportunity to be a more authentic version of yourself.
Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.
How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?
In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.
As a part of this interview series, I had the pleasure of interviewing Kelsey O’Callaghan is the Co-Founder and CEO of Dorai Home.
Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
I grew up in Salt Lake City, UT. I’ve always been super active, I inherited that from my parents who moved to Utah for their love of the mountains and outdoor lifestyle. As a child I was fairly precocious in how I approached creative projects and eager to please in school. I grew up playing soccer, it was my passion and that same love has translated into running for me over the past decade. My dad is very entrepreneurial and hard working, and while I’m fairly risk averse, seeing someone as pragmatic as him take on new ventures gave me a sense of confidence in taking control of my future. I knew in college I would want to eventually have my own company. I went to college on a soccer and academic scholarship in California. It was there that I realized I was equally interested in graphic design as I was in business, so I decided to major in both which gave me a unique dichotomy when it came to exploring career options. After college I moved to San Francisco and got a true taste of startup life, innovation, and learned so much from the mentality of those around me.
I have one older brother who shares my sense of humor so we get along well. I’m fortunate that my brother, parents and myself all live within 15 minutes of each other. We’ve also been a super active family. I can’t remember a weekend going by without soccer games, basketball, skiing, etc.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“There is real magic in enthusiasm. It spells the difference between mediocrity and accomplishment.”
This quote really speaks to me, I am not actually familiar with who said it, but for years I’d had it around work stations. It resonates because at the end of the day, the biggest variable we can influence with respect to the outcome is our mentality. Our mindset and emotional reactions really shape the way we perceive the world and why not bring enthusiasm to whatever it is that you’re taking on. That’s pretty magical 😉
You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.
Qualities: Determination, Perceptive/observant, conscientious
Examples: Determined — This is both a blessing and a curse, but when I get my mind set on something, it’s no longer an optional, it’s I’ll keep chipping away at it until done. I wanted to work in San Francisco after college so I emailed hundreds of companies (90% went unanswered) until I got 3 offers to secure my move. I’m continuously trying to improve and reach my potential in running. While managing all the stressors of life, I want to break 3 hours in the marathon and I’ll keep training and going after it or fail along the way — but I don’t shy away from hard work. In starting Dorai Home, I held all of the brand, design, photography, and creative aspects to a really high standard even though it was just a Kickstarter campaign because I’m determined to see what we could become, instead of taking an easier path.
Perceptive/observant — This has helped me as a designer, I’m very aware of how people interact with physical or digital products, I spent the first 8 years of my career as a user-experience designer. I love listening to interesting podcasts about psychology and human behavior. I tend to overanalyze situations because I pick up on a lot of details that typically go missed. This has helped me in my research for new products for Dorai Home. I’m aware of trends, able to make informed decisions and understand human-centered design because it comes really natural to my brain.
Conscientious/Thorough: In general I have high standards for myself and others, and like to do tasks to the best of my ability. I’ve had quite a few people tell me to ‘tone it down’ and try doing things at 75% (including Jason 😉 but it’s just not the way I operate. I feel really fortunate for the opportunities I’ve had in life and it encourages me to show up and apply myself. How we show up in life is the most controllable variable, it’s worth it to see what happens when you operate at your full potential.
Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?
Prior to starting Dorai, our eco-friendly home goods company, I worked for a number of design agencies in the Bay Area and then a design agency in downtown Salt Lake City. I thought it suited me because I have a really active mind, and get bored easily, so I figured the change in projects would keep me more fulfilled.
I worked as a User Experience Designer and Researcher, primarily focusing on digital experiences. I collaborated with other eager designers on projects across industries with a range of clients from large established companies to emerging startups. When I moved back to Utah, I helped bring a lot of the skills from my experience in San Francisco to a local agency and spearheaded the UX design and brand strategy capabilities.
It was fine the first 5 years and I think being in the Bay Area presented really unique opportunities, but I wasn’t excited by the work. I felt disconnected from what I was doing and so many of the projects I worked on never made it to market (typically because of internal politics, etc). As a consultant, I was always trying to exceed expectations, but it often felt like the impact of the project was intangible or unknown. I found when working at an agency in Utah, I was getting so drained from having to bring all this energy to make client projects successful and feeling this self-induced pressure to deliver something really helpful or meaningful when that wasn’t the culture.
It was around that time I started thinking about working on my own as a freelancer and met my now husband who encouraged me to take the leap.
And how did you “reinvent yourself” in your Second Chapter?
I took a more holistic approach to health and happiness. I stopped focusing so much on productivity and work output, and instead strived to be a healthier, more energized version of myself. I challenged myself to create the day-to-day life I wanted, and then build my work life into that. I realized I couldn’t expect a job to provide a sense of purpose and fulfillment, and personally, I thrive better with boundaries.
I have a very active mind and a really strong wake drive, when I’m going through stressful periods I have trouble turning off and going to sleep. It’s an immediate signal that things are out of balance. In this second chapter, I’ve become better about taking accountability and ownership over my own mental and physical health to prevent burnout. That often means taking a half day on Friday, not setting an alarm and letting my body wake up naturally, scheduling work around a key training run versus trying to fit it in at 4:45AM.
I know that if I’m physically and mentally healthy, I’m going to be an engaged team member, more creative, and a better leader for Dorai. We hold onto being these stereotypical startup workhorses. It’s a badge to see how many hours one can put in during a week, but that’s just not necessary and it’s not what we’re meant to be doing. We’re humans not robots. Once I let go of the social stigma and guilt, I was able to see that both Dorai and I could thrive in parallel. During the first 6 months of starting a company I was feeling chronically stressed, and I wouldn’t have been able to stick it out unless I committed to prioritizing my wellbeing.
Having our own company has enabled me a platform to explore the values I care about: health, sustainability, mindfulness. It’s been such a necessary opportunity for my long-term happiness.
Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?
It was a couple of things, ultimately my now husband, who is extremely entrepreneurial and encouraging. He pushed me to start my own small agency shortly after we started dating and helped me with securing initial clients. He also picked up on the fact that I was feeling really physical run down and mentally not myself a few months later. It’s silly that I needed this, but in having a company together he really gave me permission to step back and focus on my health, knowing that things would work out.
He helped me see that I didn’t have to keep working around the clock as an individual consultant and a key founder in Dorai. We came up with a plan to phase out clients and manage our expenses to reduce some of the financial pressure.
Throughout this time I also worked with therapists and insightful medical experts who helped me change the way I perceive work and learn to actually listen to my body’s signals, instead of seeing them as a burden.
After a few months of putting my heart in creating the Dorai brand, I found it was exciting and something I could identify with in a way I haven’t been able to on client projects. I could push when I had energy to take on ambitious marketing objectives, and dial back when I was feeling run down.
Ultimately, I just know I never want to go back to the place I was a few years ago when feeling so burnt out. I felt like I was desperate for a change and there was no harm in trying and taking the plunge.
What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?
As a consultant within design agencies, you engage across a range of industries, but the work it fairly specified. I spent almost 10 years working on user experience design and digital strategy, and wasn’t sure I would be able to translate the same skills that made me a strong designer into a brand leader and founder.
I suppose I found out the most genuine way, by throwing myself into it and seeing what happens. I’ve also been super detail-oriented and intuitive, so inside I had a feeling I could figure out how to launch and create a compelling brand, or give it my best shot trying. Dorai Home was just Jason and I for the first 2 years. We have the product development and manufacturing support of Jason’s agency, Klugonyx, but at the end of the day, it was on us to figure out brand strategy, marketing, packaging, customer service, inventory planning, fulfillment, accounting, etc.
From my time living in Palo Alto and San Francisco, I adopted the mentality that you can figure out and do just about anything if you’re perceptive and willing to put in the time. I’ve brought this same mentality to every brand touchpoint for Dorai. Do research, execute, and use data to help guide you along the way.
I never thought of myself as an e-commerce brand strategist and creative director given my analytical tendencies, but it’s a skillset I hadn’t yet maximized because the opportunity to blend the roles wasn’t available. I now understand how much goes into creating a very compelling brand that resonates with consumers, and it a skillset that comes somewhat naturally.
How are things going with this new initiative? We would love to hear some specific examples or stories.
Dorai is doing great, like any new venture we’ve had our ups and downs, but 2020 was a good year for us. We grew 240% and our goal is to keep listening to our customers, creating innovative home products, and changing the way we think about sustainable materials.
2019 threw a number of tough challenges our way that forced us as a business and personally to be more resilient and smarter about the way we market and grow. We began experimenting with more ad channels, testing larger volumes of creative assets, and doubling down on how we communicate our value propositions.
Personally, I feel so much better mentally and physically. And I’m witnessing first hand that it’s possible to prioritize yourself while launching a business. I’m a big self-quantified nerd, so I track a lot of biomarkers and have seen such a shift in where they are today versus 2 years ago due to my efforts around stress reduction. My HRV is much more consistent, I get sick less often, my REM sleep is 3x more than it use to be, my digestion is worlds better, I’m physically less tense and exhausted. It’s pretty wild!
Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
I’ve mentioned him a few times now, but my husband is extremely supportive and balances out my type-A tendencies by helping me put boundaries between work and life. He’s the one who will physically pull me away from my computer if it’s 7pm and I’m still trying to check things off the list (this happens too often, but I appreciate that he’s stubborn and keeps tabs on me).
He was also the one who was bold and confident enough to want to start a product-based company, which is something I wouldn’t have ever taken on individually.
I’m also really appreciative of my close friend Renee. We met when we both moved to the Palo Alto and were 2 fish out of water living in a sea of startup engineers. She fully understands what it’s like to want to thrive as a business owner but not at the expense of one’s personal health. She’s so grounding and easy going that I can confide in her when it comes to business or personally advice and she can fully empathize.
Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?
Absolutely, I frequently feel a sense of imposer syndrome. Not a week goes by that I don’t feel this strange guilt about getting paid from Dorai because I don’t know if I’m doing everything that a proper executive should be. I’ve also struggled with the idea that I’m doing enough even if it’s not the conventional 40+ hour work week, which makes me question if I’m dedicated enough or willing to sacrifice what it takes to be a founder.
I overcome this by working on my internal dialogue and channeling these flawed beliefs. I’ve been going to therapy for a while to gain these tools. I listen to helpful podcasts that help navigate these emotions, and seek out other founder’s stories to realize everyone is just trying to do their best and learning along the way.
Here’s an example, I remember early in my consulting days, I would try to have the answer to everything and always be on. Then I read a study that showed that leaders who are willing to admit that they don’t know something are often perceived as more knowledgeable and trustworthy. I started implementing that in client meetings and instead of trying to come up with an answer, I would simply say, “I actually don’t know that exact answer, but I will research after this and let you know.”
I love listening to podcasts, and the more that I listen to intelligent people, the more I notice how willing they are to admit they don’t know things or talk about ‘failures’. I’m such a big believer in having sound data to make decisions. As long as I have enough data points, I have confidence that I can move forward knowing that I’m doing the best I can with the knowledge I have on hand. At the end of the day, who says you can’t thrive as a founder even if your approach looked different than the conventional expectations?
In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?
This is something I personally had to learn the hard way because for some reason (which I admit is so silly), I struggle asking for help. I hate feeling as though I’m burdening others by asking them to do something if I’m capable of doing it. You learn pretty early on in a startup that you can’t have that mentality, it will kill you. It’s not possible to research every answer and try to do it all yourself.
Having a company with my husband has been a huge help because we can really talk about these things and he knows me well enough to push me to get support, which I need. I’ve built out a great team of contractors who I enjoy working with so much, and are excited to be working with Dorai. This support and having others who I can trust delegating tasks to has been life changing.
It’s also really critical to have your few key friends who know what it’s like to be in a high-pressure business situation and can offer diverse advice. I have 2–3 women who I talk with routinely about business problems, life, health, etc. We know we can always come to each other and there will be insightful advice and zero judgement. It’s critical to develop relationships that encourage you to be vulnerable and willing to put it all out there, knowing that’s how you’ll get the most helpful advice.
Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?
The entire past 3 years feels as though it’s been outside my comfort zone, but that’s where growth happens and you have to embrace the inherent uncertainty. I do that by reaching out to others who are more experienced, gathering data to make decisions, and assessing the risk associated with any action. Navigating a startup is so much around mangling risk and taking the right ones.
Personally, I like to put myself into more novel situations and then cope with getting out of my comfort zone with stress management techniques. I use an infrared sauna, I do breath work and meditate, I run 6 days a week, I focus on getting enough sleep and creating space between myself and my work. All of these help me when anxiety creeps in as I’m outside of my comfort zone.
An example of getting out of my comfort zone: about 2 years ago we were in a situation that required us to raise a small round of investment. We got through an initial screening to move onto a more formal pitch environment where we were to pitch to about 25 men and 5 women. Jason happened to be traveling that week, so it meant I would be handling it solo. I’m fine speaking in front of crowds, but this was definitely a more intense setting and I felt the additional pressure of needing to raise funds. I was struggling with anxiety going into it, but knew I had prepared thoroughly and as long as presented our value proposition and brand vision concisely that was the best I could do.
The pitch ended up going really well, the feedback was positive and overall it helped me become a better communicator in that style of business setting.
Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why?
- Letting your less-poised, imperfect human side show is an asset to connect with others and an opportunity to be a more authentic version of yourself. Ex: For whatever reason early in my career I adopted this mentality that I should always be perceived as professional and stoic to be a good employee. I even recall in a performance review, a manager struggling with how to articulate that it’s okay to just let things go a little and be a little more human. I reached that conclusion when I started working with a lot more like minded people and realized the trust that comes when you create human bonds. We’re so use to operating in this arbitrary 8–5 schedule that’s better suited for robots than humans, and the more that I’ve shared my imperfect qualities and opened up with others, the more they share with me and we have a more positive work environment.
- It doesn’t have to be all or nothing when starting a business, it should be sustainability built into your life to thrive. No startup journey is the same. It doesn’t make you any less dedicated because you’re doing it part-time while working another job, or the head of a household that doesn’t allow you to work a 10-hour day. Ex: I really struggled in this area because I felt so pulled between not giving enough of myself to Dorai but also feeling the need to keep going client work because that’s what paid the bills. Too often we hear about the founders who sold everything and slept on a mattress to achieve their dream. That’s fine, but it’s not the only path to do it. It’s okay to not work 50 hours a week on your startup if that’s not sustainable. I found that I did better having a sense of financial security from my clients until Dorai was generating enough revenue that it could pay a percentage of my income that I felt comfortable with. This was not the advice I got from many advisors who encouraged me to ‘take the risk and dive all in’, but I worry if I did that I would have put too much stress on myself and burnt out.
- You don’t need a lengthy track record or prestigious degree to lead a successful company. Being a founder is more about your ability to stay enthusiastic and strategic through the inevitable peaks and valleys. Ex:These certainly do help, especially when it comes to getting initial investments, but I would rather collaborate with someone who is hard working and conscientious than someone who comes from an impressive background. As long as you’re willing to learn along the way and not succumb to the inevitable feelings of defeat, you’ll figure it out. I have found the best contractors (and leaders) are often those who don’t come with a sense of entitlement but are eager to prove themselves. Jason is the perfect example of this.
- A startup goes through phases similar to raising a child. At first it requires so much hands-on attention and guidance, and it’s shaped entirely by you. Eventually it will start to morph and take its own direction. You can’t try to control the outcome forever but instead provide a vision and path to get there, even if it’s different than how you originally planned. Ex: We were so involved in all the roles when we started Dorai and had total control over every brand touchpoint, but eventually as you grow that’s not sustainable. I remember feeling this sense of anxiety when we had to start handing things off or take risks to grow that meant we wouldn’t be as hands on. It ended up being so pleasantly surprising to see the outcome of working with a talented marketing group who saw new creative ideas we didn’t think of. Even changing the name from Bath Mat to Bath Stone was something suggested by an early customer and friend. It’s so exciting to witness the influences that external forces have on an entity if you’re willing to let it grow.
- It’s essential to create space between your identity and the business to establish a more realistic view when setting expectations, unless you’re Elon Musk because he’s a super human 😉 Our own biases distort priority and importance. It’s easy to become all consumed by inheriting the stress of the business as our own, instead of applying a more appropriate level of problem solving. Ex: The very first manufacturing experience was a bit of a nightmare (like so many others) and we were delayed by months, we had to change fulfillment centers, etc. This is not the initial customer experience you want to deliver as a premium brand. I totally spiraled into this stressful period and felt that I personally was letting people down and that this was so unacceptable. This wasn’t healthy, it put stress on my relationship and ultimately made me consider not pursing Dorai all together. I’ve since learned the valuable lessons that if you’re transparent and over communicate, most customers are very reasonable and understanding. Additionally, it’s better for you to see yourself as one small component of the business rather than the key driver of the business in order to stick with it for the long haul.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?
This isn’t going to be the sexiest answer, but I honestly think if more people in power analyzed and acted like behavioral economists, the world would be a better place. We’re in a time where every issue is so politicized and layered with subjective emotions that we don’t even realize our own biases. If we were trained to look at data and make more objective decisions around a universal set of values, we’d see more progress across all areas. This would yield more sustainable policies that would have a lasting impact.
We can strip away a lot of the unnecessary emotional polarization and focus on finding the best solution based on data. We could conduct experiments around the issues that really matter and let the results speak for themselves then scale them.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. 🙂
There are so many! Beyond the stereotypical ones like the Obamas, Jason and I would LOVE to go on a double date with Kristen Bell and Dax Shepard. But if it really came down to it and I could only choose individuals who might see this 😉 it would be Rhett and Link from Good Mythical Morning, I love their genuine dynamic and they seem like such funny, down to earth people. I relate to Link in so many ways that it would be fun to have a long lunch and just talk.
How can our readers further follow your work online?
You can learn about our company Dorai Home at http://doraihome.com/
I share frequently on our Instagram stories.
Thank you so much for sharing these important insights. We wish you continued success and good health!