“I’m here trying to help people on a daily basis with my gig, and I get to hear that I help people pretty often, which is great.”
Taylor Kreiss, Positive Psychology Coach
Taylor Kreiss works as a writer, speaker, and life coach who specializes in using research-backed psychological and philosophical principles to help people build a meaningful life and boost individual wellbeing. Here he talks about the struggles of building a practice around something people don’t know they need, what to consider before becoming an entrepreneur, and the difference between seeming to have everything and living an authentic life.
What do you do as an entrepreneur?
I feel like that’s a question about my personal mission to some extent, which is to use philosophy, positive psychology, traditional psychology, and really the science of wellbeing to help people achieve their own version of their best possible life. I’d say that’s kind of my goal as an entrepreneur. There’re larger questions about what entrepreneurs have to do, or like the spirit of entrepreneurship, but that’s how I interpreted the question.
What would you say drew you to this vision?
I grew up among some unique people, people who society would look at as being overwhelmingly successful. You know, we’re talking about billions of dollars, world championship athletes, and people who were running overwhelmingly successful businesses; the kinds of people who, from the outside, seem to have everything. But the fact of the matter is, if you were in the inner circle, or were spending every day around these people, you would very clearly notice they were suffering from personality disorders, substance abuse disorders, there was attempted suicide, there was domestic violence. It was something that looked beautiful from the outside but from the inside there was a lot of difficulty.
And that’s been a splinter in the back of my mind; it always stuck out to me that people who were achieving the American dream, or at least appeared to be, in its traditional sense of being more successful and wealthier and having more prestige and being more famous are not necessarily any happier than anyone else. For me, that became something I wanted to make sense of and resolve for myself and for other people—to correct our priorities, our values, what we’re pursuing, what we think of as a “good life” so that we don’t put in 60 years of effort, to end up really wealthy and super miserable. So that’s what led me to this idea of helping people achieve their best possible lives and through my career—gaining knowledge as I went along—it drove me towards philosophy as an undergrad, positive psychology as a master’s, and now actually into becoming a therapist.
Did you have any fears about becoming an entrepreneur?
Yes, absolutely, especially in the domain I’ve chosen for myself. It’s not like I’ve invented the new app that’s going to light up Silicon Valley or something like that. It’s not like I have some product that’s very clearly in need and people seek it out on a daily basis, at least as of right now. Like, you seek out therapy. People need that. They’re in pain and they need to solve something specific, but people don’t as often see the value in “I’m ok, and I just want to be doing better.” It’s funny—for most people actually, if you ask them what they want out of life, they’ll say they want to be happy, but they’re not about to drop $80 to $100 an hour to see a coach to actually achieve that. I think a lot of it comes from a stigma that’s associated with life coaches and self-help. There’s a lot of charlatans out there wearing crocodile smiles and basically stealing your money. But for someone who genuinely wants to be a positive psychology coach, you’re relying purely on your own initiative to find clients in a domain that is not very secure. You know, I’ve definitely given my sales pitch and had people be like, “Oh, ok. You’re a life coach,” and just turn off entirely. So it can be scary to think you’re trying to make your living and surviving in a space where people are highly skeptical of what it is you’re doing.
What has been your greatest struggle in your coaching practice?
I guess if I had to drill down a little bit, it’s the salesmanship aspect. I don’t like imposing on people at all; I’m one of those people who is sort of hyper-conscientious about ever asking for favors, of feeling like I’m pressing on someone—let alone trying to sell my own services. I’m not sure why that’s so difficult for me. I’ve noticed, actually, in the MAPP [Master’s of Applied Positive Psychology] class or other people who are going to apply positive psychology in their professions, that they tend to have difficulty with it too. Like, “This is my passion project.” A lot of the daily work feels like you’re talking to a good friend of yours, so it’s strange to sell that as a service.
When people ask what you do, you’re in a spot right then where you’re basically involved in salesmanship, and that has always made me very uncomfortable. But that’s absolutely necessary to surviving in this space. You need to grow comfortable with selling your services. I think that’s been the toughest part, just learning to be a salesman, or a more business-minded person rather than just someone who really cares to hear about other people and want to help them. You know, the two almost feel at odds with each other, at least at first look. I’ve had people before who were like, “Oh, you want to be a writer? I’ve got something for you to write for me.” And you’re like, “Well, I want to charge money for that,” and they’re like, “Oh, if you really liked this, then you’d do it for free” kind of thing. There’s a whole Twitter dedicated to just the weird crappy responses that people have given when an entrepreneur tries to charge money for their services. When you’re a little more in the creative space or working with people on health and happiness, it becomes much easier to play down what that service is worth or to feel like you’re asking for too much and it’s a little strange to be a salesperson.
Another thing with working in the positive psychology or coaching space that’s been funny for me—because a few people have said this to me—is: “You look too young to be giving people advice about how to live.” I’ve gotten that a few times, and it’s something that’s stuck with me. I’ve coached people who were in their sixties. It felt natural and we developed rapport, and the dynamic was actually fun and interesting for the people I ended up working with, but I’ve had a few people where I say that I’m a life coach and they’re like, “Dude, you’re like, what? Twenty-five maybe? Thirty? Who are you to be giving people advice about how to live?” As an entrepreneur or someone working in coaching, or going into therapy and being under thirty, some people are like, “Dude, you don’t know anything about life. How could you?” That I think has been a unique point of contention.
What has been your greatest triumph in your journey thus far?
My mind travels pretty quickly to working with one of my first clients. We spent six months or so working together, and we sat down for a review of my services and to quantify the kinds of changes he’d experienced in that time. He told me that he had achieved more in those six months than he had in like a decade of traditional therapy. That is something I look to whenever I’m feeling discouraged, or like I’m not good enough, or thinking, “What could I possibly know?” or “How can I possibly help people?” That I think is probably my greatest triumph. I’m here trying to help people on a daily basis with my gig, and I get to hear that I help people pretty often, which is great, but that was a particularly amazing testament of my service. If I start to think I might be lacking in experience because of my age or that I don’t have enough educational training because I’m not a psychiatrist of 30 years or something, I remind myself of what he said. He told me straight out he’d been seeing a therapist for a lot of his life, and the bit of work that we’d done in positive psychology had done the most good for him, and he thought working with me was an especially good match.
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Taylor Kreiss, Positive Psychology Coach
What do you think the reason was that he was so successful?
I inquired further, because I love hearing about how awesome my services are and I want to know more about why they were so great. He mentioned that he thought he and I had an especially good rapport, which I know from some studies is actually considered to be just as, if not more, important than the modality of treatment sometimes. He also felt that he had spent just countless hours on a couch talking about the traumas of his childhood and that, by delving into a new space with something he’d never really tried before, he found there is a lot of beneficial work to be done by focusing on the positive side of the spectrum. You know, positive psychology is a pretty new field and most people haven’t heard of it, haven’t really tried those kinds of interventions. With traditional therapy, you end up sitting down and addressing what has gone wrong. That’s of course helpful and beneficial, but it basically never happens where you stop and just consider what’s going really right in your life—what are your character strengths, what are you already supremely good at and how you can be leveraging those things to be doing better on a daily basis? He really seemed to respond to that in particular. He considered himself to be a highly creative person. He thought that was integral to his identity and to his wellbeing, and it was something that was lacking in his life. Digging into where he was, what his goals were, setting active strategies to get there, and then the accountability really seemed to have an effect on him.
Another thing that he said that was interesting to me was that his therapists didn’t really give homework as much as they should. That was a big focus of our practice: Every day he would have to send me photos of some creative project he was working on. I was like an accountability buddy. I was making sure he was getting it done on a daily basis, and that was just a tremendous help, whereas a more traditional therapist would focus entirely on his traumas with his childhood. He’d walk out [of the other therapists’ sessions] and would feel better for a little while, and over the course of a month, it sort of drains away from your moment-to-moment consciousness, whereas daily activities seem to have a more consistent bolstering effect on your wellbeing.
What’s been your biggest sacrifice as an entrepreneur?
A certain kind of lifestyle is the thing that pops to mind right now at least. In the beginning especially, and even at certain times when it’s famine more than feast, you never know if you’ll have enough cash around. So you got to reduce your expenditures pretty drastically. You need to prioritize success in your work endeavors and then just enjoy your work enough that you’re willing to sacrifice like, getting the shiny new Xbox One or living in a larger space that’s newer and has a dishwasher. The kind of small things that many of us take for granted.
I was working as a bartender for a long while in a really nice restaurant and had some solid and consistent paychecks where I could live a little more like a baller. If I were to go out on dates, I could take my dates to nice restaurants, to get some excellent drinks, or to have unique and extravagant experiences, or, just on my own, I could eat better food and out more often. I could live in a nicer place. I could drive a nicer car—so on and so forth. When I decided to really go almost all-out into my entrepreneurial lifestyle, I read a lot about the importance of dialing back your lifestyle a bit so you can ensure you’re making enough money to actually pay your taxes at the end of the year, or quarterly to deal with all of your expenses as an entrepreneur, to also account for the fact that sometimes you’ll wrap up with two to three clients at once and you’ll need to find new ones; they’re not always as quick to come as in other moments, so I’d say you kind of need to sacrifice…“quality of life” doesn’t sound right, because I feel like I get a lot from being an entrepreneur and from planning my own schedule, and from doing work that I love. But the kind of material quality of my life, or what many of us associate with “success” in America, which is driving a nice car and living in a nice apartment or house. That might have been a difficult thing upfront or something that an entrepreneur should really think about before delving off into being their own boss entirely, but that’s what’s required a lot of the time.
What’s been your biggest failure?
That’s tough. I feel like it would be different if I were the kind of entrepreneur who had created a product and launched it, and spent a lot of money and time and energy and had it fall into the ground and not work out or something, or if I had any kind of moral failures as someone working with peoples’ mental health or anything like that. But I’ve never had any moral failings or launched a product. I tend to look at shortcomings as more learning experiences, so it doesn’t strike me as some one event that stands out, but I guess I would have thought I’d have more clients earlier on, more quickly, more consistently, even after years. I figured it’d be a lot easier, or that I could always just depend on being a coach to make a living, but that’s one of the major reasons I’m going back to become a therapist now: It’s a lot easier when you have a license to do something, when you can bill insurance, when you can deal with peoples’ pain, not just their pursuit of bettering themselves. It’s just kind of hard to sell your service. Even in the MAPP program, I ran into a ton of coaches who had been at this for decades and they looked at me pretty seriously and said, “Think twice before you make this your primary career.” Even now, I think that a lot of coaches need to have another job where they have to work as a waiter or something to make ends meet. It’s pretty difficult to make it as a coach. I know there’s a lot of coaches on Facebook who love to advertise they’re making six-figure salaries and they’re driving around in Ferraris and stuff, but it’s mostly an illusion from my understanding of speaking with anybody who’s a coach on a day-to-day basis.
Did anyone in your life try to dissuade you from becoming an entrepreneur?
Yes, totally. People in my family, people very close to me who hold a lot of sway over my decision-making, said that it was not a good idea to become a life coach or to become someone who’s working in positive psychology because there’s no demand for it. They worried people don’t think about it the way I do, and, if they’re interested in it, they’re not going to pay the kind of money I need to get by, and that I’m making a huge mistake with my life. So, you know, definitely a lot of naysaying as I approached this way of being.
Has anyone in your life been a constant source of support?
Yeah, absolutely. Scott Barry Kaufman, my mentor out of positive psychology. Jer Clifton also was the first person who helped me to change the trajectory of my life towards positive psychology. He works at the positive psych center, too. A handful of people out of my cohort at MAPP, for sure. I think that something you learn in positive psychology is the importance of curating your social group. You don’t want to make a point of hanging out with only people who tell you: “You suck,” and who don’t want you to succeed. You want the opposite if you’re trying to achieve success; you want to derive strength from each other. You want to share practical knowledge. You want to have a tribe to help you achieve your goals, and I definitely formed that through positive psychology—the nice thing being that people who are involved in positive psych tend to be the really supportive, helpful, kind of folks that you could send a random email to them having never met them in your life and ask them for advice, and they’ll generally help you out. Those mentors and a group of people out of positive psychology, I could call them right now and they’ll drop whatever they’re doing to help me out.
Tell me about your work-life balance.
For people who work as digital nomads or who are trying to get their own thing off the ground, it can be hard to set really definite times, like, “I’m only going to work 8 to 5”—especially as a coach or a therapist or someone who works in mental health. I’ve had people call me literally at one in the morning and be like, “Oh, I’m so sorry. Am I waking you? Gosh, is it ok? If you wouldn’t mind, could we just talk about this or that?” But between my desire to help and the fact that I’m not usually asleep until 1 o’clock, it’s not an issue for me and I actually enjoy sometimes being available at all hours of the day and night.
I personally have never been a person who’s given to workaholism, though. In general, my work-life balance is more towards working to live rather than living to work. Even during my work, it’s part of my life, so I don’t have too much of an issue there. I know a lot of people do. I’ll have to think about this a lot when I start school again in September. I’m sure things will get ridiculous, but for now it’s pretty wonderful.
I guess I should say that in my life design, when I sat down and tried to consciously envision or determine what my future should look like in order to make myself as happy as possible, I was like, “I can’t stand having a boss. I don’t want to be somewhere when someone else needs me there every day.” I want to be able to determine my own schedule. If I feel like only working three to four hours a day on average, then I want the ability to do it. I picked a profession that just so happens to coincide with all of my interests, my passions, my values, where I don’t have to overwork myself or drive myself nuts. My schedule is just one or two clients a day, which leaves the rest of the day to go hang out with my dog and recover from whatever’s going on in my life.
Did you ever think about giving up?
Yes, absolutely. All the time. At least in the sense that we can’t control our spontaneous thoughts, you know? It just rises up in your head and you’re like, “Oh, God, what am I doing? I really should have just become an engineer, or continued working at my bartending job where I was making good money”—because it’s so nice having security.
I totally understand why people go that route of just having a job. I don’t think there’s anything wrong with: “I go to work during the day and it’s not some purpose or some passion or some calling. I make my money, I make my living, and then I do what I like to do in my free time and I enjoy my job enough.” That’s fine. It’s so nice just knowing you’re going to have a paycheck every two weeks. When you end up in a moment where you’ve got your two to three consistent clients, but a lot of your other really short-term clients drop off, and you’re thinking, “Oh, God, I have to renew my registration and get a new car battery, and my license just expired and I have to pay my taxes at the end of this year.” There’s like $8,000 outstanding. How am I going to find clients immediately? It’s not something that you just run out and ask people in the street if they need a life coach. It’s almost every moment of the day, you have stressed-out, anxiety thoughts that are catastrophic and that you’re going to end up not being able to pay your rent. Those are moments when you’re constantly like, “Yeah, I should probably just go back to bartending, go back to school, get a job in engineering so I know I’ll have a comfortable, reliable existence.” So, that’s kind of the war, you know? There are pros and cons for almost every lifestyle, and some people have more or less risk tolerance, or are more able to control their anxiety thoughts than others. Then there’s people like me, who are just stressed out and do it anyway.
What would make you feel like you accomplished what you set out to do with your coaching practice?
There’s a great exercise used in coaching or in positive psych where you imagine you’re sitting at an event and you’re, like, seventy-something [years old]. You don’t know what the event is. The announcer comes out on the stage and says, “We’re all here to celebrate the lifetime of…” and it turns out it’s you. You’re getting your lifetime achievement award, and the point of it is to try and understand why you’re receiving that award. I think that’s a good exercise for this right now, which is, “If I were to receive an award for being a successful coach or therapist, what would that look like?”
I think it’s a pretty quick, easy, intuitive answer: It’s just to have helped a whole lot of people achieve a greater degree of wellbeing in their lives. Specifically, if people were to go up on stage and thank me for whatever I’d done, it’d probably be more existential in nature. People would get up there and be like, “Hey, I was always kind of following what I thought society wanted me to do. I was following the ‘American dream.’ I thought that if I got more money, power, and status, I’d be happy. But as it turns out, I wasn’t. I didn’t know what to do. I heard about this guy Taylor, and he introduced me to some concepts in philosophy and some theorizing from positive psych or from traditional psychology that helped me develop my own understanding of how to live authentically and how to be happy and how to live a life of meaning. He empowered me with the kind of behavior modification science needed to actually achieve my goals and he held me accountable. In our own way, we had a really fun time and I consider him a good friend.” If I could have that kind of effect on a lot of people over my lifetime, I would say that I’ve achieved my goals.
What’s the most important lesson you’ve learned as an entrepreneur?
That’d be tough. I guess it would be to“do it for the right reasons, to know that this is the lifestyle you want for yourself. Like, you’re not just trying to make a bunch of money without doing a lot of the work, or you want quick success and power and fame. An entrepreneur is intent on their goals and ready and willing to get into the trenches and to do well for themselves and others.
This interview has been lightly edited from an in-person conversation for clarity. Capturing Lightning is a project from Woden, a strategic storytelling agency in Philadelphia that helps organizations articulate who they are and why people should care. To learn more about how to tell your story, visit us at wodenworks.com.