Pursuing Entrepreneurship On Your Own Terms With Tara Claeys

Tara Claeys: Thanks so much. I’m really happy to be here, Jennifer. Thanks for having me.

Jennifer Bourn:

So, you’ve got a busy agency, adult children, and a spouse, but you started your business when your kids were a lot younger. I’d love to start with your origin story — how you got to where you are today.

Tara Claeys:

Well, I started out in the advertising world. I had a good foundation in marketing and did a variety of things, including wearing a taco suit on a street corner as a marketing director for a gourmet business. You know, when there’s no budget, there are things that you learn how to do. You have to wear a lot of hats when you’re working for small companies so I had experience there.

And when I had my first child, my husband was working really long hours, traveling overseas for weeks at a time, and I just couldn’t stand the thought of putting my baby in daycare. And so, when I weighed out what I was making versus what it would cost, all of the things resulted in us deciding for me to stay home. I have always been very creative. I like to doodle and draw not fine art but I used to do little illustrations for coworkers.

And after I had my son, I went and told my boss that I was going to be quitting, and she said, “Well, you have to start a little craft business, making the illustrations that you do.”

And so I did. I went and got business cards made and just started networking with moms’ groups and doing my illustrations just to give myself a creative outlet, really.

And then, within five to seven years, I had full-scale stationary business. And then it became more graphic design as I started to use the computer more and I really loved it. I did Christmas cards and would go to craft shows at Christmas time, but I just decided at one point, that I didn’t want to spend my Christmas doing that anymore. And so I stopped working with paper and I had built my own website and a couple of other websites and decided I would dive in and, uh, was introduced to WordPress.

Growing up, my dad and my mom were very crafty and we used to go to craft shows. They used to make belts out of leather and these bracelets, and I would do macrame, and we’d go to these craft shows with all these hippies back in the seventies and early eighties.

So, I had a good entrepreneurial foundation that my parents raised me with, which really helped me to have the confidence to run my own business, whether it was this small little thing. I remember I was so excited that I could pay for the piano lessons for my kids, or I bought a minivan one year, and that was just a big deal to me that I had enough money to do that.

Jennifer Bourn:

Yeah, that’s amazing. And I love the story — your parents setting that example of being creative and following your passion. Going to all those craft shows and hitting the road, and pounding the pavement, and showing up, and hawking your wares, and saying, “Look what I created,” and selling that to people.

My dad built furniture on the side all through my childhood. It was one of those things, right, “I like my job but there’s something else that I’m passionate about. There’s something else that I’m interested in.”

And, I love that you got started with just something that you enjoyed doing. It started as a side hustle. And sometimes we have no idea where that’s gonna take us.

Tara Claeys:

Right. Yeah.

Jennifer Bourn: When I first started doing freelance work I’m like, “I’m just sitting in my kitchen making things look pretty for other people.” We don’t give ourselves, I think, enough credit for the talent and the creativity that we bring to the table to do those things.

Did you ever imagine that you would be running a digital agency?

Tara Claeys:

No, of course not. Not at all.

I’ll also add there’s some very, very strong sense of validation — ego feeding — that happens when someone likes what you’re doing enough to pay you for it. And then it can also be very challenging when people don’t wanna buy it. Right? So it takes a lot of, fortitude because you know that there’s gonna be ups and downs.

Jennifer Bourn:

It definitely takes some grit, especially in those early years. And when you are more craft-centric than business-centric, you are creating from your heart and get emotionally tied to that work.

I find that it’s a little easier when I’m creating for business. I’m solving a problem. I’m removed from my work a little bit more so it’s a little easier when things don’t go perfect or somebody doesn’t love everything you do right off the bat.

But when it’s that true creative work, especially for crafters and makers and people that have those kinds of skills, you do get so emotionally invested. It is tough.

Tara Claeys:

Yeah. I think that’s very true. There are a lot of risks that you take.

Jennifer Bourn:

And sometimes, if we’re honest, we are our own worst critics. We judge our own work so much harsher than somebody does from the outside.

And I know you’ve mentioned in the past, kind of that dichotomy of being a Jack of All Trades among specialists. And I know that dynamic has played out for you in different ways in your business. How have you juggled that push and pull of being that Jack of All Trades and then also dealing with expectations of specialty?

Tara Claeys:

Yeah, I think it depends on what specialty means.

I was a fine art major and communications major in college but I was never fully trained in a design school. But I think I’m a really good designer and I have good design sense. I’ve certainly done it a long time.

I didn’t go to school to be a coder either but I can do a really good job building a website. So, I understand those things. That’s where the Jack of All Trades Master of None comes in. That idea that I’m good enough at all of these things and making sure that I know when I need help and when I need that expert.

So I think expert versus specialty is maybe what I’m describing in terms of specialization in a business audience or in a vertical or something like that. That’s also a direction that I’ve gone.

Having done very general work for all different kinds of businesses over the years, I decided that I wanted to specialize in something and become known for that. So, I chose to work with schools and nonprofits because my heart’s in it.

You talk about your passion, right? You mentioned doing something that I enjoy doing. I enjoy working with that content, with those images, with those clients.

I had worked with several before. And deciding that I wanted to become a specialist in that type of organization was a decision that I made a couple of years ago actually, at your Content Camp program is where I really dove into that. And I haven’t really looked back.

I think I do a better job because I feel more connected to it rather than in another type of business, like a dentist or a lawyer or something like that. Certainly, I’ve built those types of websites but I didn’t enjoy them as much as I do working with schools and having now done many school projects, many nonprofit project.

I can be confident I understand the needs of those types of projects. And clients can have more trust in me that way, too.

Jennifer Bourn:

I really love the fact that you started out as that Jack of All Trades and then decided to focus because I think that’s relatable for so many people. We start our businesses and we just need experience. Like, I will do anything somebody will pay me for — I need experience. I need to build my portfolio. I need projects under my belt.

It really isn’t until you get into actually doing the work that I think you figure out what you like to do and what you don’t really like to do, and what projects light you up and what projects drain you. so I love the fact that you got out there and just started trying things and doing things.

And so many people these days are self-taught because they found passion and desire and drive and curiosity. But there does come a point where it is in your best interest to focus. And you chose education, nonprofit, schools, clubs, things of that nature. Now that you have that specialty, how has choosing a focus helped you bring that value that you can?

Tara Claeys:

Yeah, that’s a good question.

It’s a privilege to be able to do that, I think, to get to a point where you can take that risk.

And I remember sitting at your Content Camp and writing content for my homepage of my website and changing it to completely talk only about schools and nonprofits and thinking, “What am I doing?”

Like, I could have no one come to me and I could have no clients and have no business and I’m going to be turning away people. It is a risk to do that — to get to a point where you feel comfortable enough and confident enough, where you can financially take that risk.

You don’t start out that way. I don’t think many people do and I certainly couldn’t have. So, like anything else, you have to pay your dues and you have to learn. And whether you’re a generalist continuing on still, you’re learning things as you go, and you’re becoming better at what you do, and gaining confidence. So, I think it’s important to acknowledge that.

It wasn’t something that was really comfortable at the beginning, to take that risk, as much as I was excited about it. But I think now, having done it for a couple of years, I feel really confident in what I know because it forced me to dive in and study not only the needs of these types of projects but also what other companies who are serving them are doing.

Attending webinars by my competition, which I don’t consider myself to be a competitor to big giant companies, but I learn from them and see what they’re doing. So you gain a focus on the types of things that are being done in that industry.

And you have to learn about what the challenges are in that industry So I think. It’s not just knowing that I can design a really great-looking website and I know what content should go on the homepage for a school. It’s also, I know that the marketing person in that school is also the secretary or the administrator answering the phone calls at the front desk.

And they’re going in a million different directions. And so how can I build a website that’s easy for them to use and that they know they can trust me because I understand where they’re coming from. So it goes way deeper than even just understanding how to build a website for your specific niche.

Jennifer Bourn:

That’s a great reminder that when you do specialize, you become such a valuable asset for the clients that you serve because you understand them better than anybody else, or you understand the little nuances of their job and their role and what they’re responsible for and what they have to do, and can help make that job a little bit easier.

And there is tremendous value in that.

But there’s also a lot of value in showing up confidently as the business owner, and that can be really hard for a lot of people, especially if you’re newer to business or you’re leveling up.

Imposter Syndrome and the anxiety that goes along with that — it’s a very real thing that many of us deal with on a regular basis. And I know that you have said this is something you’ve dealt with throughout your business. I’d love to hear how that showed up for you and how you got through some of those times where you start second-guessing yourself.

Tara Claeys:

Yeah, for sure. And that goes back to the idea of how validating it can be to have someone hire you. It can also be really soul-crushing to not be hired or to make a big mistake, which some I still can lose sleep over. I remember once when I was working at MCI in their direct mail department, before the internet, we published the wrong phone number on a mailer. Like, there was a number transposed on it and I think I lost sleep for months and months over that.

Those experiences stick with you but they’ll help you not make that mistake again. So, I think part of it is understanding that you’re not perfect. And I have a really hard time not being hard on myself, so it’s easy for me to say but not to do. It takes me a long time to get over a mistake.

And I also will look at things that are amazingly well done and just feel horrible. Like, “I can’t do that. How did they come up with something so wonderful?” I compare myself a lot. That also is a mistake that you can make. Comparing yourself to others in these days of social media, whether it’s your work or what you’re wearing or — there’s so many comparisons you can make and it’s easy to get hung up in that.

And I think for me, Imposter Syndrome really lies deeply in that comparison and the idea of comparing myself to other people. And as far as how I overcome it, I mean, I’m in my fifties now and I can’t say that I have mastered that at all.

I certainly rely on my friends and colleagues to help boost me up when I’m feeling low. That’s a great thing about the WordPress community specifically, and I think the freelancer community as well. It’s that we’ve all been there and being able to support other people when they’re having a hard time, and knowing that you can reach out and vent or cry or complain when you’re feeling low, is super helpful.

For me, if I can just get it off my chest and have somebody say, “It’s okay, you’re okay, you’re good at what you do.” Just hearing that from someone is really helpful. I meet with a therapist when, you know, when things are too much for me to handle and that’s been a really important thing that I’ve done as well.

And meditating is something that I have tried very unsuccessfully.

Jennifer Bourn:

Okay. I’m so glad that you said that because so many people I know all say meditation is this magical thing for them. And for the life of me, I can’t. My mind’s all over the place. I’m thinking about things I struggle with that. So I’m so happy that you said that.

Tara Claeys:

Yeah, I have tried all the apps. I have tried all the things. And I have the Peloton app and they have some good meditation for falling asleep and I will say, I will play those sometimes when I’m trying to fall asleep and they will help me.

I’m very goal driven and habit driven. And I set a habit that I have to meditate for one minute before I open social media. And I was pretty successful at doing that for about a month and then I lost the habit. So I need to pick that back up again.

There is a type of meditation called Loving Kindness — and I don’t do it formally but I do think about it a lot. And that is, closing your eyes for a minute. And there’s a little mantra that you say: “May I find peace.” Just giving yourself that little bit of quiet can be helpful.

And then I also exercise every day, which I find to be very helpful in terms of just finding some time to think, and just feeling good about myself physically.

Jennifer Bourn:

It definitely helps. And I think it helps the tone of the day. I work out in the morning because it is a time to focus on showing up as my best self. And sometimes I work out in the evening if I’m having some rage and I just need to get it out so I can relax in the evening.

But I love that you mentioned therapy as an option. Several people on this podcast have mentioned, at times, speaking to a therapist and how great it is to be able to have the option to speak to a neutral third party who’s not invested, who can give you that fresh perspective from the outside, and just a safe space to say all the things and not be judged.

Also, I love that you mentioned comparison. That is so detrimental but is so hard to not do, right? You can’t compare yourself to somebody else. What do they say? Somebody else’s highlight reel.

Or, somebody who’s in a different stage of life.

When I started my business, I think I was 27 — I might have been 26 — but I was comparing myself to people who are 20 years ahead of me, right?

Or, when you have kids and you’re trying to run a business and be a mom, and you’re dealing with all that. You can’t compare yourself to somebody who’s single and doesn’t have any kids.

And I know you built your business while your kids were at home. You mentioned not wanting to put your child in daycare as one of those driving things for you. How did you juggle being a mom and running a business?

Tara Claeys:

Yeah, probably not that well.

When my kids were little, I didn’t work very much. So I had this little craft business and it didn’t really take that much time. At Christmas time, as they got older and I was busier, they saw me getting stressed out a lot.

I think both of my kids would say I am a total workaholic. So, even when they were in school, I was focused on my clients and not disappointing them, and not making mistakes.

I remember once I picked my daughter up — I had been sitting in the car waiting for her — and I was on my laptop on a hotspot and it was, like, a registration for this fitness website that I was doing and it wasn’t working. And I remember freaking out. And she’s sitting there in the car. She’s driving and I was trying to fix this thing from a hot spot and it wasn’t loading and I was about to have a breakdown. And I look back on that with so much guilt because of the impression that I know I left on my daughter in that moment, and if I could go back in time, I would. I would probably change that.

As my business grew, I was not very good at balancing that.

Jennifer Bourn:

It’s tough. I mean, when I’m all in on my business, I feel guilty that I’m not doing enough for my family. And when I’m all in on my family, I feel guilty that I’m neglecting my business or I might not be there for my clients — and that push and pull can be so, so difficult.

And the example that you were setting — being a workaholic — I so feel that because I spent, I mean, years in my business working every single day. Even on the weekends and, I feel fortunate that they were really, really little so they don’t remember the worst of it. They just remember I was always there. But they also were able to see us decide to do business differently and to make a change for the better.

So I think we have these moments where we look back and we’re like, “I can’t believe that’s how I managed things or that’s what I did or that’s the experience we had.” But our kids also see us choose better. They see us choose to make a change and to be intentional about how we’re approaching our business or what success looks like to us or growth.

How over the years, since having that realization that you are a workaholic — probably also a very much perfectionist — changed or shifted your approach to what success looks like to you or what growth looks like in your business?

Tara Claeys:

Yeah, that’s a good question and it’s probably, of course, like everyone else, changed over time. I used to have a podcast, called Hallway Chats and we talked to people in the WordPress space. In one question, we asked how they define success and everyone has a different measure for that.

And I think it changes as you get older and as things change in your life. I recently lost a good friend to cancer and, um, a family member as well, and so when you have that happen as well, that changes your perspective on what success is. And, it’s almost a cliche that they say, no one ever said they wish they worked too much on their deathbed. Right?

I do think about that a lot. I love my work though. And so, I think there’s a great amount of guilt that’s put on people who work a lot because you’re supposed to have this work life balance and all that.

I really like work. I like making websites. I love figuring stuff out. And so I’ve stopped trying to beat myself up about it. If I want to sit and read a book, I can sit and read a book. But I choose to work, not because it’s due or because I have over-scheduled myself, but because I like it, and so admitting that to myself has been very liberating.

It’s a little bit scary because I wanna have other things in my life and I do, but it’s sort of my default go-to thing. When it’s a rainy Saturday, I’m excited, like, “Ooh, I get to go fool around on this one website or fritter away on something that I like.

So, that has really been a shift in my mindset that I’ve embraced. I read this book, when I turned around, when I turned 50 — Designing Your Life. And it had you sort of map out things — do a deep dive into what you enjoy and what you prioritize in your life.

And this was around the same time that I was making this decision to specialize in school and nonprofit projects. And so it all kind of fit together for me at this time where I was defining what I wanted my life to look like.

And, I don’t feel like I ever really put much time into planning, because I got in this track, right?

Graduated from college, got a job, got married, had kids, did these things that are just fitting into this puzzle that’s sort of set up in society — and I hadn’t really given a lot of deep thought to:

• Who am I?
• What do I want my life to look like?
• What’s your legacy?
• What are you here for?

For me, I want to enjoy myself. I want to be a good person. I want to be a good citizen — all that stuff — and how does that fit together? Because how I define myself, I think, is really important so it’s consistent.

Jennifer Bourn:

I really love the distinction between work because you’ve over-scheduled yourself, you’ve over-committed, things are a little bit out of control, and you have no choice. Versus work because you’re excited about it and you can choose to do it.

I love that you’re making that distinction that you are saying, “When I have time available, what do I want to work on? What do I want to do?”

There is such a big difference between being behind being over-committed, being overwhelmed, being overworked, and working on the weekends or on the evenings because you have to and you have no choice. And then being able to have a choice and saying I’m doing this because I love it, because I enjoy it, because it fills me up. I’m here because I want to be not because I have to be, and I can walk away at any time.

Tara Claeys:

And that’s a really important thing too when you work for yourself. I can decide that I’m going to take the rest of the day off. I can decide I’m going to take the week off.

Jennifer Bourn:

Well, and I love the notion of designing your life — of being really intentional about saying, “What do I want my life to look like? How do I want to spend my day? What do I want to be doing?

Being intentional about that sets you up to live the life you choose, not just the default.

Tara Claeys:

Yeah, a hundred percent. I value the times that I can decide it’s a nice day. I’m going to go for a hike. I know that’s a great thing that I can do too, and I do enjoy that as well. So yeah, it’s filling in the downtime with things that I love. That’s success.

Jennifer Bourn:

I adore that definition of success.

And a lot of times it’s tied to revenue. What kind of revenue do you want? Where do you want to get financially? And I’ve always said as long as I can swipe my ATM card and I don’t ever have to think twice about that swipe, I am happy. There’s not a number I’m trying to get to.

More important for me, is being able to have a choice in how I spend my day and how I spend my weekend. Flexibility is more important and more of a signal of success for me than anything financial because that signals to me more balance.

I don’t know if you ever have balance. I always look at it as sometimes work has to come first, and sometimes life has to come first. And family and friends or whatever it is. And as long as none ever takes the reins for too long, you’re okay. Right? And some of that is a choice.

Tara Claeys:

Yeah, the financial piece is another comparison element. I mean, I think when you go into the entrepreneurial space, a lot of what you are fed is, you know, six figures, seven figures, and that that’s the goal. And for many people, that is what drives them.

And it certainly has created, for me, a great sense of insecurity because if you’re not growing by leaps and bounds, are you successful? That’s how we typically define success in the entrepreneurial space. How much money are you making? How much have you grown?

And I remember thinking it was super important to me that I reach a certain milestone in income for no real reason, except that I thought that’s what I had to be at in order to be successful and to be included in the club of people who are successful. And I’ve been fortunate that my business has grown, but I don’t really pay attention to those numbers as much as I used to.

Jennifer Bourn:

I think you hit the nail on the head with the entrepreneurial space and it being all about money, right? It is hit six figures, hit seven figures, hire these people, grow. What are you launching next? Who are you hiring next? What’s the next position you’re bringing in? What are you launching?

All of these things — it’s always the next thing, the next thing, the next thing. And it almost makes you think if you’re happy with where you’re at and things are really good, there’s something wrong with that. And there’s definitely nothing wrong with that.

Tara Claeys:

Well, and here’s the other thing it’s not even really a valid comparison that you make. Because I have almost no overhead. I have a few contractors who work for me. But I have a few friends who have started marketing agencies, they have office space that they pay for. They have full-time employees whose livelihoods they’re responsible for. And so they don’t pay themselves some months because they have to support their business.

I’m not interested in that. Like, I don’t want the stress of that. And I made a choice long ago, not to grow to that degree.

I’m never gonna make a million dollars. I’m never gonna have a million dollars in my business, nor do I want it. But businesses that have a million dollars in income that does not mean that they’re making more than me at the end of the day. And I don’t think that we think about that, right?

Jennifer Bourn:

Isn’t that the truth? There are so many misconceptions around that, it’s not even funny. their top-line numbers might be really amazing. But when you dig in and you look at what they’re actually paying themselves as the owner, some of these people who are out here, you know, hustling and bustling as a freelancer or as a solo are actually making more.

Tara Claeys:

Right. Yeah. And I sometimes say maybe if I was 25 years younger and I was looking ahead to build something that I could sell, if that was my intention, maybe I don’t think so. I don’t think it’s me, but the people who do that — they love it. I think that comparison is what people mostly use for success. And it’s really not a fair comparison.

Jennifer Bourn:

Yeah, I definitely agree with you. There’s this magic to owning your own business, or choosing your own path, or having a side hustle, or something of your own and getting to be in charge and call the shots It is incredibly fulfilling.

Tara Claeys:

Yes, it is. as I’ve said before, I love it. And having satisfied clients is great too.

Jennifer Bourn:

So, let me ask you this. What tool have you found that you wish you discovered earlier?

Tara Claeys:

I suppose Slack because I solve a lot of problems that way and I communicate with my team and I communicate with my colleagues and friends. So having a communication platform that’s not your email has been really helpful. I’ve just developed a community in Slack.

Jennifer Bourn:

I love it. And I think it goes back to something you said earlier having a community to go to for support, to be able to vent, to bounce ideas off of, to get a little bit of help when you need it.

We were just talking about this the other day in one of the programs that I run — in Profitable Project Plan — and we were talking about the power of having a place to go, a safe community of people to turn to when you need help with a project. You’re not sure what to do, you’ve got a question, you’re in a weird spot, you’re curious what somebody else would do. To kind of vent about something and figure out how to handle it before you take it back to a client.

To have something like that in your life or your business — to have community — is so important and so powerful. And then to have a tool like Slack, to not only connect in your own business, but to bring people together and to have conversation.

Tara Claeys:

Yeah. I’ve made some, hopefully, lifelong friends through our Slack group. So I just… I can’t say enough about it as part of my daily life.

Jennifer Bourn:

That’s amazing. And when things don’t go according to plan, when the poo hits the fan, how do you stay in a positive head space?

Tara Claeys:

That’s really hard to do.

I’m not great at it. I mentioned the support of the community.

I think, I’m able to move on when I know I’m forgiven. When I know someone can relate. So you can say, “I messed this up,” And just to have somebody who I respect and who has been there say, “It’s okay,” that helps me kind of move it off the front of my mind. And then trying to make it right. Having closure on mistakes as much as you can, I think that helps

Jennifer Bourn:

Well, I appreciate the advice to just deal with it right away, to reach out to community and get some support. There’s so much power in having someone say, “Oh, I’ve been there. It’s okay. It’s going to be fine. You’re going to deal with it. You’re going to get through it.” That reassurance is so helpful when you’re in that mode of stress.

The faster you deal with it and the faster that you have a solution in place, the faster that you can move past that. When we put it off and ignore it or let it linger or let it fester, doesn’t it just get so much worse?

Tara Claeys:

For me, it does. Some people really have a hard time facing things head-on, and I think that would be really hard for me I can’t let it fester I gotta have closure on it. Yeah.

Jennifer Bourn:

I try really hard do that but like you said, we’re not perfect.

With that in mind, what would you say to someone who is working on building their own version of whatever success looks like and maybe they are stuck in that mode of comparing and they might be a little bit frustrated?

Tara Claeys:

I think that there’s some value that comes from comparing yourself to others in that it can motivate you and teach you how to do things better. So I would say, when you’re comparing yourself, use that as more of an education than as a way to beat yourself up because you can eventually get there.

So, consider who you’re comparing yourself to. Perspective is really key when you’re in that comparison mode I think. Giving yourself a little bit of grace and thinking about the perspective of the situation is really important. And be patient with yourself.

If you look back, any of us look back, at things we did when we started, they were not as good as they are now for sure. And when you look back at what we’re doing now, we’re going to be doing things better as well. And also, things change, trends change, software changes, all of those things. So, I think giving yourself some grace and some patience are important.

Jennifer Bourn:

I love that. Grace and patience and perspective. Three very important things and that’s such a fantastic way to wrap things up.

Tara, thank you so much for being here — for being open to having this conversation. Where can people connect with you online if they’d like to continue learning more about your agency? and what you bring to the table?

Tara Claeys:

Thank you. Thanks for having me. This has been fun. So, my agency is called Design TLC and my website is DesignTLC.com. You can find me @TaraClaeys on Twitter, on LinkedIn as well, so those are probably the best places to reach out to me.

Jennifer Bourn:

Fantastic. And for those of you listening, if you enjoyed this episode of Seeking Satisfaction, subscribe for new show updates at Jenniferbourn.com/seeking-satisfaction. And hey, leave a review on your favorite podcasting platform.

If you would like to hear more from Tara and learn her 12-week goal-setting process for setting goals, scheduling tactics, improving productivity, and being accountable to those goals, check out the Seeking Satisfaction Extra Minutes Membership.

Members receive extra minutes from podcast guests like Tara that provide valuable training to help you do business better. You can find details about the Seeking Satisfaction Extra Minutes Membership and Tara’s training in the show notes at Jenniferbourn.com/021.

Until next time, may you live inspired, embrace imperfection, seek satisfaction, and have a fabulous day.

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