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Season 2 – Episode 2:

The Art of the Pivot: Tina Essmaker

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The Art of the Pivot: Tina Essmaker

Episode Summary

After an unexpected end to her work, Tina Essmaker had to pivot, and fast. In this week's episode, we talk to her about how to successfully manage transitions, drawing on your past to help create your future.

Episode Notes

A pivot can be a powerful thing. Tina Essmaker started as a social worker with a side project, a Kickstarted magazine she founded with her husband. But when her marriage ended, she had to re-evaluate: stay with the magazine, or start something new? She decided to tap into her skills as a social worker and her connection to the creative community to re-launch as a creative coach. In this week's episode, Damona talks with Essmaker about how she transitioned from publishing into a self-created role where she helps creative workers identify and stick with their goals.

Essmaker offers concrete tips for people considering a shift from one path to another, and encourages listeners to consider the "emotional balance sheet" of their lives. (And Damona gets a gold star for her ability to describe her work concisely - would you get the same?) "It’s just a continual act of faith, that knowing what I’m doing is valuable and it’s needed, and then trusting that clients will come to me," says Essman, who now works as a coach, a speaker, and a writer.


To learn more about Tina and her services go to:

Word of Mouth Marketing- Article

Nielsen Report

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Damona Hoffman:         Welcome to the I Make a Living Podcast by FreshBooks. I’m your host, Damona Hoffman, and I’m one of you, an entrepreneur who is constantly learning and evolving. This sometimes makes my job a little hard to define. In a nutshell, I help people find and improve relationships, and as someone who has helped singles for nearly 15 years, I know that when a dude writes “entrepreneur” as his occupation on his Tinder profile, it sometimes means that he lives at home with his mom and dreams of one day owning a business. Hey, no shame in the game, we all have to start somewhere. However, according to our guest for this week, creative coach, Tina Essmaker, we all need to master the art of defining our business to draw in potential clients, especially in the early stages of entrepreneurship.

Damona Hoffman:         How do you define your business?

Tina Essmaker:              When I say that I’m a coach for the creative community, what I mean is anyone who considers themselves creative or wants to be in that creative world of play and discovery, and using their imagination. The business is really Tina Inc, right? It’s Tina Essmaker as the umbrella, and I am my business and then under that, I coach, I write and I speak. So I don’t see any of those things as the number one business, I see all of those things as being equal, and they crosspollinate and support each other and they all feed into each other.

Damona Hoffman:         I know as an entrepreneur myself that does many things and has many hyphens to my name, and also identifies as a creative, sometimes that’s hard to describe when you go to a cocktail party and people say, “What do you do?” There’s all these hyphens after it. How do you coach people in how to answer that question in an authentic way?

Tina Essmaker:              Okay. This is one of my favorite exercises that I like to do with people. So if you had to describe what you do without saying the company you work for, the name of your business, or the title of what you do, how would you describe it?

Damona Hoffman:         You’re asking me right now?

Tina Essmaker:              Mm-hmm (affirmative) mm-hmm (affirmative).

Damona Hoffman:         I talk to people and I help people learn how to communicate better.

Tina Essmaker:              Awesome. You nailed it.

Damona Hoffman:         Did I?

Tina Essmaker:              I feel like you’ve done this before.

Damona Hoffman:         Can I get a gold star?

Tina Essmaker:              You do.

Damona Hoffman:         No, I haven’t, actually. I haven’t, and this is really good advice to be able… because I get tongue-tied when people ask me. It depends on what setting I’m in, sometimes I’m a host, sometimes I’m a dating coach, sometimes I’m a mom, and there’s all these roles, in addition to just whatever your professional role is. Sometimes it varies based on who you’re speaking to, right?

Tina Essmaker:              Mm-hmm (affirmative). Yeah, and also people sometimes don’t have context. So if you said, “Well, I’m the host of a podcast,” people might not understand what that even entails, right? So if I say, “I’m a coach for the creative community,” people might say “Uh-huh (affirmative)-,” but they have no context. So instead, when I’m at a party or anywhere, I say, “Well, I help people like you discover what’s possible for their work and their lives.”

Damona Hoffman:         And then people lean in-

Tina Essmaker:              And that communicates.

Damona Hoffman:         -and they’re like, “Tell me more.”

Tina Essmaker:              Mm-hmm (affirmative) And it communicates the value of what you’re doing, right? Because throughout our lives, the company we work for might change, our titles might change, the roles we play in our lives, right? You just named like five or six different roles that you fulfill in your life, and our roles are always changing, but the value that we contribute is, it’s the meat and the heart of what we do. So if we can go beyond titles and roles, and really focus on, “This is my contribution to the world,” that’s much more profound, and it’s also just much more interesting and compelling to tell someone at a party that, versus, “Oh, I’m just a title,” or “I just work at such and such company.”

Damona Hoffman:         Even though Tina works specifically with creatives, she stresses to everyone the importance of learning creative ways to introduce ourselves and our business, even if we’re not in an artistic field.

Tina Essmaker:              So I think we’re all creative, number one. Especially as children, right? We all have these wild imaginations, and as we get older, I think that creativity is, we unlearn it, in many ways. But for me, creativity is anything that is nontraditional, really. It’s taking a path that maybe no one else has taken, or taking a path that doesn’t have, there’s not a clear point from A to C. So yeah, I think that creativity is much more broad. It’s not just visual arts, it’s people who are building their own businesses, it’s people who are solo entrepreneurs, it’s people who maybe work full-time somewhere in-house, but they have a side project that they’re pursuing, or a passion that they’re developing on the side. And creativity can be for us, or it can be something that we do and put out into the world that we get paid for as well.

Damona Hoffman:         All business owners are inherently creatives. At the core of our success is the ability to imagine a business solution, and then build it from the ground up, and that takes creativity. But even as a creative problem solver, sometimes life throws you a curve ball and you are forced to reevaluate. What do you do when you’re faced with a different kind of business problem? The unexpected hard pivot. This has happened to me several times in my business, when I had a second child and I had to restructure my business model as a solopreneur to fit in the time for a new baby, and then again when my TV series, which drove much of my promotion, was canceled. I had a choice: quit or evolve. Tina specializes in guiding creative professionals through that exact kind of career transition. She’s good at her job, because she’s been through a few tough transitions herself.

Damona Hoffman:         And I know you’ve held a lot of different titles and had different iterations of your business. Can you talk a little bit about your journey and what brought you here to be a coach for creatives?

Tina Essmaker:              So at 18, I applied for this youth care worker position, and it was at a runaway and homeless youth shelter in my hometown, and I saw the social workers who worked there and I thought, “Man, they’re really contributing and having an impact in a tangible way, and I want to do that. I also want to be creative, but I don’t know how to take a creative path. So maybe, I should take this more traditional, safe path.” Well, no one told me social workers don’t make money. I stayed at the same nonprofit after college for about six years. In the meantime, I met and married my husband and he was creative as well, and we had both wanted to do something different than we saw our families doing, and from the beginning, we had talked about making a magazine. And five years into being married, I’m doing social work, I’m starting to feel burnt out already, and he was doing web design and working for a lot of clients locally, and-

Damona Hoffman:         You were like, “Let’s have another project.”

Tina Essmaker:              Yeah, let’s-

Damona Hoffman:         “We need that.”

Tina Essmaker:              Why not? Well, we kept putting off this dream of working on a creative project together, and finally we said, “You know what? We are never going to do this, unless we force ourselves,” and so what that looked like, was we turned our living room into a studio, we gave away our TV, couch, coffee table, everything. So there was literally nowhere to lounge in the evenings, which forced us to get in the mindset of working on this side project, at the end of the day after work.

Damona Hoffman:         So you’d come home exhausted after what, a eight hour, 10 hour work day, and then you’d go right back into working on your passion project, on your side project?

Tina Essmaker:              Yeah, I mean there were breaks, right? And it wasn’t every night, but it was a lot of nights and weekends, and we spent months… I’m trying to remember the timeline, but I think it was probably close to six to eight months really working on the idea and refining it, and simplifying it so that we had something that was sustainable that we could ship. And so, we named the project The Great Discontent, which-

Damona Hoffman:         Where did that come from?

Tina Essmaker:              The name came from a mentor who said, “You have to learn to be content in your discontent,” meaning that it’s okay to have ambitions, and it’s okay to want something more than what you have, but know that you will continue to metabolize your accomplishments and achievements. So you’ll probably always have a sense of restlessness and discontent, and that’s okay.

Damona Hoffman:         That’s a lot to… You’re running this business with your husband, and that can be a challenge, working with somebody that you love and having it not affect the way that you communicate as a couple, as well as in the business. Do you feel like the publication, was it influencing your relationship at that point?

Tina Essmaker:              I think that both influenced both. So I think that our relationship influenced our desire to do this creative project together, and then I think once we were in this creative project together, it was really, there was momentum that we had to keep up with, and I don’t want to speak for him, but my experience was that in the same way that I can imagine when you have a kid, that becomes your focus, the business really became our focus and because it was DIY, grassroots, startup-esque, we were putting a lot of our time, energy and resources into the business. And in my mind, it was, “When we get to this point,” or “When we make this amount of money,” or “When this happens, then I can focus more on my marriage. I can focus more on my friendships, I can focus more on visiting family and staying in touch with them. I can take better care of myself,” and I was putting off a lot of aspects of my life to work on this side project turned full-time gig for me.

Damona Hoffman:         And that can be sort of dangerous, because when you say, “When this happens, then everything will fall into place,” or “Then I’ll be able to focus on the next thing.” But I find in my life that when I do that, then the finish line just keeps moving.

Tina Essmaker:              Yeah, you just-

Damona Hoffman:         Was that your experience?

Tina Essmaker:              Mm-hmm (affirmative) You just move the marker. “Oh, now I need to get to this point. Now I need to get to this point,” and it just never ends. Eventually, so what happened was we did the Kickstarter, we made print issues, we made more print issues, we had an online shop. We distributed the magazine to bookstores around the world, we worked with distributors. We launched a live event series in New York, which I hosted and we did 24 events in… No, we did 20 events in 24 months, published the audio to a podcast. It was amazing. It became this multimedia publication, an incredible creative community grew out of it.

Tina Essmaker:              But what happened ultimately, it was that my marriage ended, and pretty abruptly, and at that point, it was like everything stopped. And I had been working so hard and neglecting many parts of my life that I was then faced with, right? Because I couldn’t just throw myself into work, so I had to reassess everything. I can’t say if the magazine, I can’t… it’s like there’s a million little decisions and things that add up to building a relationship, and to the end of a relationship. So I can’t pinpoint exactly, was it the stress of running a business together? Was it not having boundaries of this is personal life, this is a relationship, and this is work? I don’t know. I can say there are many things I would do differently, but yeah, I can’t…

Damona Hoffman:         That must be really difficult, when you’re defined, in a way, in your professional life, you’re defined by this other thing that you and your husband had birthed, like you even said, it was like having a child, in a way. And so, you have that identity that’s wrapped up in the identity of not only being the partner of someone, the married partner, but also being the business partner. So was there a point as the marriage was ending, was there a point where you said, “I need to back away from this other entity, back away from the community, the business, the magazine,” everything that you had created, for self-preservation?

Tina Essmaker:              Oh, absolutely. So my whole life was thrown into one pot, right? My marriage, my business, my friendships, everything was enmeshed, and I felt totally defined by my marriage and my business, which people love the story of a husband and wife co-founder. People loved that. People wanted to talk about us working together as life partners, just as much as they wanted to talk about the magazine and what we did with that. And so, that had become the narrative behind the magazine too, right? And I felt loyalty to the business I built, I felt loyalty to my community, and I felt like I was disappointing people.

Tina Essmaker:              I also felt like, “Oh my goodness, I don’t know who I am outside of my marriage. I don’t know who I am outside of this business. I don’t know if anyone will want to work with me, or hear from me, or invite me to speak or be part of events if I let go of this,” but ultimately, I knew that I needed to create some space and distance to allow myself to heal and to rebuild my life, and to gain perspective on what do I want to do next, because I didn’t know.

Damona Hoffman:         But how, Tina? How do you do that when your life is totally enmeshed with this brand and this person, where do you begin? I’m sure there’s some people listening to the podcast right now who know, who know they have to make a change. What was the first step, and then how did you create that distance and redefined who you were?

Tina Essmaker:              Well, my instinct was to just stop everything and walk away, because when you’re hurting and you’re in pain, all you want to do is not be in pain. But I spoke with a mentor, I was going to therapy, I had friends I could talk to, very close inner circle, and then I had a couple of mentors who had known me through the years, and one of my mentors said, “Look, you were married for a decade. You were in business together for five years. It took you that long to build both of those things together, it’s going to take you time to untangle those things.” And so, I committed to the process of whatever it would look like.

Tina Essmaker:              What that looked like for me, was my marriage ended in January 2017, and I continued to work on the business through December 2017, because I had some commitments and I wanted to honor them, and I also didn’t know what I would do next. The magazine was my life, and so I was going through the process of getting divorced to my husband and business partner, while I was still working on the business, and that was hard. I don’t know how I did it, other than to say we decided to silo, “This is personal, this is business,” and we had always worked together very, very well. It was like a well-oiled machine. So on the business side of things, it felt like, just simply keeping up that routine and maintenance, but I gave myself a whole year, and I’m really glad I did, because I felt good about how I transitioned out of the magazine, rather than just abruptly ending it and stopping.

Damona Hoffman:         But ultimately, you stepped away from the magazine and created a new career for yourself?

Tina Essmaker:              Mm-hmm (affirmative).

Damona Hoffman:         How did you decide this thing that you had built together was now going to be passed onto him to maintain?

Tina Essmaker:              So I talked a lot about this with my mentor, because part of me wanted to retain the business and see what I could do with it, but I was also feeling really burnt out, and I knew that I needed my own identity outside of the business, because the business was so closely tied to my marriage, I didn’t feel like I was capable of moving onto a new chapter and a new identity, if I remained in something that was so closely tied to a former chapter of my life.

Damona Hoffman:         So let’s fast forward a little bit past the point where the marriage has ended, you’ve made this decision, and now you have to develop a new identity for yourself. How did you move into coaching and decide… Did you ever make a conscious choice for that to be your next path, or did it evolve more organically?

Tina Essmaker:              There was an exact moment in time when I said, “Aha! I’m going to become a coach for the creative community!” What happened was I was at a party in New York and one of my friends who works in a creative field said to me, “I’m working with a life coach, and I really enjoy the process, but he doesn’t quite understand the creative world,” and I thought, “Oh my goodness, I’ve been interviewing creatives for six years. It’s also my community and my home, plus I have a social work degree. Could I combine those two things?” And I had written down on my to-do list, my very long to-do list, “Look into coaching,” but it felt ambiguous, and I didn’t know where to start.

Tina Essmaker:              After that conversation with him, I went home, looked up programs online, found one in Atlanta that offered accelerated training. Because I had my social work degree, I didn’t want to do a whole year or two of training. I signed up. I had hardly any money, so I charged tuition to my credit card and thought, “I hope this works. I hope I can get clients and pay off this credit card bill.”

Damona Hoffman:         Yeah, we’ve all done that, like credit card charging on hope. It’s going to work out somehow. But if you’re on purpose, somehow it does.

Tina Essmaker:              Mm-hmm (affirmative).

Damona Hoffman:         So you completed the program, and then did you hang a shingle like, “Now I’m Tina Essmaker coaching” and-

Tina Essmaker:              I did.

Damona Hoffman:         And I mean, how do you get clients? How do you begin that?

Tina Essmaker:              So I signed up for the training and went to Atlanta in October 2017. So this is during the year I’m still working on the magazine and transitioning out. There’s a lot of overlap, right? So as soon as I signed up for the training, I started telling people at conferences and events, “Hey, I’m going to be a creative coach, so I’ll let you know my business launches.” I hadn’t even been trained, but for me, it felt like the only way to make it real was to say it audibly to people, and take that risk, and then I-

Damona Hoffman:         Well, that’s a coaching technique, right?

Tina Essmaker:              Yeah.

Damona Hoffman:         If it’s just written on a paper, like you said, “Look into coaching,” that’s nebulous, that’s just an idea, but if you tell people, it’s a commitment.

Tina Essmaker:              And then people started saying, “Oh my gosh, that’s great, we need that,” and also asking me questions that helped me think through, “Oh, what could it look like?” more specifically. Then I went to the training, got trained, and my facilitator, who’s been coaching for over 30 years said, “You have so much life experience, and now you have the training. Go home and begin coaching.” And so I did, and I began charging right away, and it was through word of mouth.

Damona Hoffman:         Speaking of word of mouth, thanks to our listener, DBR2020, for leaving us an Apple podcast review. DBR says, “The topics and content are so relatable. This podcast really makes me feel the sense of small business community, even though I work alone all day.” I know I can relate to DBR, hopefully you can too. We love having you as a part of this community, and we would love to know what you think of the new season. You can leave your review on whichever platform you’re listening to us right now, and that will help us to reach new people and keep growing the I Make a Living community.

Damona Hoffman:         As you heard in Tina’s story, word of mouth can make a big impact. Yet, in recent conversations with entrepreneurs at I Make a Living live events, I’m seeing this tendency to think of organic word of mouth marketing as a thing of the past. Sometimes, we would rather market to strangers than ask our community to support our business. It just seems so much easier to find clients on the internet and social media. However, Nielsen wants us to re-examine our views on word of mouth marketing. According to them, 92% of consumers believe suggestions from friends and family more than advertising. Word of mouth marketing costs absolutely nothing, and Tina’s simple strategy for promoting herself to new clients is actually pretty genius.

Tina Essmaker:              I reached out to people and said, “I’m coaching now. If you or anyone you know might want to work with a coach, reach out.” Plus, the community that had grown around The Great Discontent, many of those people followed my journey. They’re still my community, they’re still my friends, they’re still my colleagues and peers, which is really beautiful. So a lot of the people who read the magazine now wanted to work with me as a coach, because they were feeling inspired, but now they wanted to take action, and they wanted someone to help guide them and keep them accountable. So for the first year, I had a one page website that simply said, “This is my story, this is my training, this is how you can work with me, get in touch,” and then a year later, after I had coached many clients and gotten many hours under my belt, and done more speaking and writing, I created a full-fledged website on Squarespace, all by myself. I’m so proud of that, because I’m not a designer, and I launched it.

Damona Hoffman:         But you are creative. Right?

Tina Essmaker:              I am, I am. And I launched my website, and here I am.

Damona Hoffman:         Tina, there must’ve been a point where you’ve gotten all the training, and yes, you’ve worked professionally as a creative for so many years, but if you’re beginning a new endeavor and you’ve had months of training essentially, in what this specific job is, there must be a part of you that gets there and feels like an imposter, and is like, “What the heck am I even doing? What do I know about coaching?” Did that come up for you?

Tina Essmaker:              Oh, definitely. I mean, it still does. I still wonder is there going to be a day when no one wants to work with me, no one wants to coach with me? And this is part of taking a nontraditional path, because no one’s going to knight you and say, “Aha, now you are a coach and you can go out and get clients!” So I think that for me, it’s just a continual act of faith, that knowing what I’m doing is valuable and it’s needed, and then trusting that clients will come to me. But it’s not just build it and they will come, I mean, there’s a lot of marketing, there’s a lot of work, there’s a lot of reaching out to people to build a business. You can’t just build a great website and expect people to come to you. But yes, I didn’t know if coaching would work. I started calling it career coaching for creatives or creative coaching. Now, other people, and I’ve met other people who call it that, but at the time, I was just making it up.

Damona Hoffman:         I totally relate. People were like, “What is a dating coach?”

Tina Essmaker:              Exactly. And so I just thought, “Well, this signifies my specialty and the community I work with,” and then I just put it out into the world and kept telling people, “This is what I do,’ and reminding people, “I’m here, I’m doing this work, I’m available to work with clients.” And it really is, it’s an act of faith, and you never reach a point where you can sit back and relax and feel like, “Ah, okay, cool. I have it all figured out.” I’m still figuring it out. I’m still growing the business. I’m still deciding, what do I want it to look like in one, or three, or five, or 10 years?

Damona Hoffman:         Do you have a specific business plan that you wrote up? What does that look like on the business planning side?

Tina Essmaker:              Sure. So I do have a plan. I like to have a master list of things I want to achieve, but then I like to do goals quarterly. So, I have kind of, in my head, what do I need to make this year? What do I want to make each month, quarter, all of that, and then, what are kind of the high level goals and the key activities that support that? So for example, this year, one of my goals was to launch my first online course, which I did, which was very exciting.

Tina Essmaker:              The first year of my business, it was just get some one-on-one clients, and see if people are even into this idea, right? And then it was, “Oh, let’s see if I can get some publications to allow me to write for them about the types of things that I address in my coaching business.” So I definitely have a plan of how I want to build out the business and the different parts that I want to grow, but then again, it’s seeing, is this an area where my skills and the value I’m contributing, do they overlap, and is it something that people want to pay for?

Damona Hoffman:         Is there a point where you would reevaluate and see if this path makes sense for you?

Tina Essmaker:              I mean, I think continuously, I’m re-evaluating all of the time. I mean, I have other goals. So I’m coaching, writing and speaking. A lot of the writing I’m doing is more academic, like doing research, I’m interviewing people. I would like to do more personal writing, more essays and narrative-driven stuff. So I have so many ambitions, and I see coaching as this kind of ever-evolving practice that continues to be a bucket to put all of my interests and curiosities into, but I think that it’s important to always re-evaluate and I think that yes, I will reinvent again at some point in my career, and I think that all of us will be faced with these moments where we’re invited to reinvent. Either something happens, right? Like my marriage ended and I re-invented because I needed to, or sometimes we take it upon ourselves to reinvent, because we feel called in a different direction.

Damona Hoffman:         This is such a great conversation for anyone that’s at that turning point, and here we are at the beginning of the year, and a lot of times we come back from the holidays and we have all these big ideas. Let’s say someone listening is a creative, and they’re thinking of beginning this new path, but I know as a creative myself as well, it’s not easy to make a living as a creative, and it can be really scary to take that leap if you have something that’s steady and stable like you did when you were a social worker. How do you help people identify if this is the time to make that leap?

Tina Essmaker:              I mean, that’s a great question, and I have a lot of clients who are asking that for themselves. I’ve asked myself that question many times. What I want to point out, which is related to what you’re asking, is that when I was transitioning into coaching, I was taking freelance content strategy and community building work. So I had reached out to friends and said, “I’m transitioning out of the magazine, I’m going to go into coaching, but in the meantime, I’m looking for freelance projects, and I did that for 2017, and I did that for 2018 for the first year of my coaching business. So I wasn’t just making a living, doing coaching to start.

Tina Essmaker:              In 2019, I said, “Ooh, I wonder if I can cut out the freelance projects and do coaching, writing, and speaking and make a living, just from that,” and it was, oh my gosh, I was so nervous, like, “Can I do this? And if I can’t, what does it mean?” And I have done it. I’ll make less this year than I made last year when I was doing freelance projects, but I’m still making more than I ever made doing social work or working in publishing, and I’m building it myself, which I’m so proud of. So it takes a long time to build a business. My advice is if you have something steady, well, I don’t want to give blanket advice.

Tina Essmaker:              What I will say is I encourage people who have something steady and stable to keep that for as long as you can while you’re building something on the side, because you want to build something that you can leap into. Some people do take a leap very abruptly and it works out for them, and that’s wonderful, but I think most of us who are risk-averse, which is definitely me, you want something soft to land on, right? So you want to have your idea flushed out, you want to have some conversation started around it, you want to have promoted it a little bit. Maybe you have a home online for it, or you’ve started to do some events and talk about it publicly. So begin to build what you want to go into before you leave a thing that you’re in, and I would say do it for at least a year. There’s always overlap. There is no such thing, from my experience, as you’re doing one thing, you quit it and you move into the next thing.

Damona Hoffman:         Yeah. There’s a lot of overlap. And even in your story, there are a lot of places where your past experience may have seemed like something completely different.

Tina Essmaker:              Mm-hmm (affirmative).

Damona Hoffman:         Social work, how does that relate to the magazine? But you found a way to marry it all in the end, and use that experience in your coaching work today. So I think nothing is wasted.

Tina Essmaker:              I agree.

Damona Hoffman:         Do you have a motto that you like to live by now? Is there something that you always share with your clients to help them frame the way they’re thinking about their business or their next creative endeavor?

Tina Essmaker:              Well, I really like to look at work and life as a season, so nothing lasts forever. Also, something doesn’t have to last forever to be good or valuable, or be an important contribution to the world. So I want to make note of that, but I look at seasons. So for the next season of your work or life, what do you desire? What are your goals? And that can change, because we have this thinking that when we make a decision, it’s a forever decision, and whatever I do next with my business, ugh, I have to do that forever, but no, that can change. You can pivot, you can reinvent. So just for the next season, maybe that’s the next quarter, maybe it’s the next year, maybe it’s the next three years. So think seasonally, which makes sense, because-

Damona Hoffman:         I love that. I love that Tina, though, because so many people say, “What’s your 10 year plan?” And for creatives, you don’t necessarily know your 10 year plan. I can predict what I’m doing six months from now. 55 months from now, it’s a little less clear, right?

Tina Essmaker:              Agreed.

Damona Hoffman:         So I think that’s great advice. Tina. A lot of times when we’re starting a new business, especially if you’re leaving a steady gig, you think, “Well, I have to be successful. If I don’t make a living in the next three months, then this was a failure.” And I wonder as you’re working with creatives, if there’s a period of time that you have people assess their success within, or how you prepare them to take this step, if they’re leaving something that’s really more of a steady gig?

Tina Essmaker:              We really need to give ourselves space, whatever that looks like. Is it three months, six months, a year? And then defining success on our own terms, so that we’re working toward what we want. There’s this really… I forget who the quote is by, but it’s essentially, “Is your ladder leaning against the wrong wall?” So do you climb to the top and then realize, “Oh my gosh, this is not my wall, this is someone else’s. I don’t recognize what’s up here. This isn’t what I wanted.”

Damona Hoffman:         Right.

Tina Essmaker:              So we really-

Damona Hoffman:         Or you look at your boss’s job and if your boss’s job doesn’t appeal to you, then you’re probably on the wrong ladder.

Tina Essmaker:              Mm-hmm (affirmative).

Damona Hoffman:         But I liked what you said earlier about even though you’re making less money, you’re fulfilled in a different way, and I’ve been trying to redefine this for myself in business, because we’re so conditioned to go for a certain financial marker, and that when you write down your goals, it’s like, “I have to make this much money,” but what is your time worth? What is the ability to put your workout time in your calendar? What is the value of being able to go to your son’s school, like I did this morning, and spend time there when I couldn’t have done that when I was working 60 hours a week at an executive job. So like you said, redefining that goalpost, and I think we have to put happiness in it as well, don’t we?

Tina Essmaker:              Yes.

Damona Hoffman:         There are other markers than just money.

Tina Essmaker:              I agree. It’s the emotional balance sheet, right? It’s like, okay, maybe this job brings in money, but what else is valuable to me in addition to money, right? So like you said, is it time with your son, is it time with your family? Is it having control over your schedule? Is it being able to set your own goals about projects that you want to work toward? It’s all those things for me. So thinking about being in a place where I was working all the time and neglecting many aspects of my life, to everything stopping and having a moment to reassess, I decided there were things that were important to me in addition to money, right?

Tina Essmaker:              Money is important, and we need it to pay our bills and survive, but I wanted to continue to be able to take care of myself, in this new way that I was, to nurture myself and my relationships, and be able to travel and have flexibility, and I have all those things now, and I’m making a living. I’m making more than I did as a social worker, which is like “Wow, I went to school for that,” so it feels pretty incredible to have reassessed everything and reinvented, and come out on the other side, and I’m sure I’ll go through it again, but I’m pretty proud of where I am now.

Damona Hoffman:         What Tina said here is probably one of the biggest keys to successful transitions, acknowledging your own accomplishments and being proud of yourself for getting this far.

Damona Hoffman:         Tina, we like to end each episode with tips and tools. So in this segment, you tell us what are your favorite tools that you use in your business or any tips that you like to share with your clients, friends.

Tina Essmaker:              Well, be very involved in your finances, know everything that’s coming in and everything that’s going out. I like to use an app called EveryDollar, which helps you literally track every dollar, because for years, I was not involved in my finances, because I came from the Midwest where typically, it’s very gendered roles in terms of who handles money. And once I was on my own and starting a business, I was like, “Oh my gosh, I have to manage all of my finances personally and professionally,” and so, getting over my fear of money and just diving into the numbers was really helpful, and do it from the beginning. When you’re starting a business endeavor, have an accountant, have software that you’re tracking your finances with.

Damona Hoffman:         Like FreshBooks, for example?

Tina Essmaker:              Yes, like for example. And they are not-

Damona Hoffman:         We did not pay her to say that, you guys.

Tina Essmaker:              They are not paying me. But it’s true, you need to be on top of from the start, because if you’re not into the numbers when you’re making a little bit of money, when you’re making a lot, it’s going to be overwhelming. So know what is going on with your money at every time, at all times. And I’m a huge fan of Google Calendar. I have everything color coded. I like to use the tasks function in there, and then on your phone, in the app you can do reminders. So actually, it’s called Goals, I believe. So you can set goals if you want to work out three times a week for half an hour, or you want to call a friend.

Tina Essmaker:              And so, what I like to do is, this is a big tip, is if it’s not on the calendar, it doesn’t happen. So the things that are important to you that might not be business related, put those in the calendar, like time to call a friend or family, journaling time, time at the gym, whatever you need to do to take care of yourself as a person, so that you can run your business, put that in your calendar and make it non-negotiable.

Damona Hoffman:         Pro tip, when you finally get around to organizing your calendar, your life will change completely. My husband and I started sharing a Google Calendar about a decade ago, and it’s made a world of difference. Now if only I could do something about this overloaded email inbox.

Damona Hoffman:         It has been such a pleasure talking with you, Tina. Thank you for being on I Make a Living.

Tina Essmaker:              Absolutely. Thank you for having me.

Damona Hoffman:         I am a big believer in business coaching, and it comes in all specialties and structures, but coaches all have a few things in common. They provide you with an outside perspective on your business. They help you create clear goals for yourself, and they keep you accountable for those goals. Even when I’m not participating in a coaching program, I think it’s really important to get advice from my peers. I wonder who you turn to for advice. Let’s start a conversation. I’m always looking for some good suggestions from fellow entrepreneurs. You can tweet me at DamonaHoffman, and don’t forget to implement Tina’s great takeaways from today’s episode: find a creative and concise way to describe your job. Put less pressure on the outcome of your transition, rather, enjoy the journey and let your business unfold as you go. And don’t get too comfortable, re-evaluate your goals at least quarterly. If you’re in the midst of considering a creative transition, book your first free consultation on Tina’s website, tinaessmaker.com, and be sure to follow her on social media at Tina Essmaker, for updates and more great advice. We’ll put all of those links in the show notes.

Damona Hoffman:         This podcast was brought to you by FreshBooks, the number one cloud accounting solution for small business owners and their teams. Do you want to know more about how you can save hours on accounting paperwork and focus more on your business? Then head over to freshbooks.com/imal to receive an exclusive offer from us. That’s freshbooks.com/imal, short for I Make a Living. Our audio engineer and composer is James Morris, producing and direction comes from Paco Arizmendi, and I’m your host and producer, Damona Hoffman. You can connect with me at Damona Hoffman, or at damonahoffman.com.

Damona Hoffman:         We’d love to see you at an I Make a Living live event as we travel North America and the UK. Go to imakealiving.com to find out when we’ll be in a city near you. Whatever challenge or transition you’re facing right now, just remember, it’s your business. See you next week.


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