Kelsey Daingerfield Full Interview Transcript
INTRODUCTION AND PATH TO SELF-EMPLOYMENT
AJ: Welcome to this episode of the Thriving Through podcast. Today, my guest is Kelsey Daingerfield. Kelsey, welcome to the podcast.
Kelsey: Thanks for having me.
AJ: Tell us about your path to self-employment.
Kelsey: That's a good question. It is quite the squiggly line. After college, I graduated when the economy kind of tanked a little bit, and so I worked a bunch of different part-time jobs. I was in aerospace medical manufacturing doing marketing, and I was there for a few years. I was doing a bit of customer service and marketing and project management. I just wasn't filling my cup, and I was recruited to Starbucks to run a store—two totally different industries. While I was doing that, I was able to really hone in on my project management skills, process improvement, team management, all that stuff. Really, emotional intelligence, I think, really developed there because you're working with so many different people.
From there, I moved into higher ed. I started out as an admin, and I worked my way up to Director of Admissions Systems. From that, I got my PMP, my MBA, and I was thinking this still doesn't feel right. So I shifted into the PMO, feeling a little bit like Goldilocks. By the end of that, I was on maternity leave, and I thought, you know what, let's just explore because I've been in a bunch of different industries.
The common thread here is process improvement, change management, working with people and teams, and helping take ideas and make them come to life or fix operations that we have. I started just tinkering. What could this be? What could it look like? I got a couple of clients, working as a side hustle doing operations management and special projects. It got to the point where I couldn't do both anymore. It was starting to be a little bit too much, and so my husband and I came up with our financial goal—if I can bring in a minimum of this, then I can leave.
I got there, I saved up some money as my backup, and as soon as I got there, I just said, okay guys, I'm giving a one-month notice, I'm out. It was two and a half years ago, and I haven't looked back yet.
DEFINING SUCCESS: BEYOND THE NUMBERS
AJ: And you have, in that two and a half years—are you where you expected to be at the two and a half-year mark?
Kelsey: I'm actually further in many different ways. I think you look at success—you define how you look at success. At first, to me, success was financial. It's like, okay, I want to surpass my corporate job. I surpassed my corporate job, and then I did almost double within the first year. I think it was 13 months, and I was thinking, holy moly, this is cool.
Then I hit a new number in my second year. Now I'm looking at it as numbers are great, but I'm starting to look at success as the balance that I've always wanted. It's not even a balance, it's a blend. It is the lifestyle shifts that I'm able to have and the things that work for me—that's not just a dollar amount every single month that I'm seeing come in. So I feel like I've hit another level with that. I took more vacation than I ever have last year, and that was awesome. My business still flourished, it still did great, my clients were supported.
AJ: That's wonderful. I remember with my son, when he started first grade, and I realized, I'm self-employed, I can volunteer in the classroom. I don't have a boss that I have to justify this to. But I still had a corporate mentality of I've got to be working all the time during work hours, and it's really liberating when you can let go of that and recognize one of the reasons you became self-employed was for that freedom.
Kelsey: Exactly. I find myself still being in that corporate mentality every once in a while, and I think, I have to be at my desk. And then I go, okay, no, we're going to leave and go work at the coffee shop because we can. We're going to rebel, and it kind of pulls you back out of it. Reset—no, I own this, this is mine. I'm going to do what works for my schedule.
THE WRONG CLIENT STORY: LEARNING TO SAY NO
AJ: So tell me, you had an interesting story when we did our pre-interview. Tell me a story about a challenge that you've overcome in this first couple years.
Kelsey: One that comes to mind is knowing when you shouldn't take a client. I find when you get started, you're a couple years in, or even your first year, you're just thinking, I've got to get clients, I've got to fill my books, I've got to get everything moving, cash. You kind of say yes more than you should.
I think that as you're evolving, you start to realize what you like, what you don't like. It's like dating. When you have your own business, when you're meeting with new people and clients and prospects, you're dating. I think you need to trust your gut a little bit. I had a client that reached out and was saying, hey, I want to work with you, I want you to come in and be a fractional COO and help me run my business. Cool, completely new industry, never was in it before.
I just had some reservations about it, and it wasn't necessarily the industry, it was the decision-making of the person that I was working with. Just some flags that came up, and nothing wrong with that. There are different personality types. Instead of just kind of sitting back and thinking, what is this, I said, no, let's do this, let's work together. It ended up feeling like I was forcing things—both of us. We were adjusting the contract and doing all these fine-tuning things.
When you trust your gut and it feels right, you kind of just go for it. This just felt like little things, and I had a little voice saying, this doesn't feel like flow with a lot of the other clients, where it's just let's do this, we'll figure it out, let's sign the contract, we'll edit it as we go, and let's just start fixing things and having fun.
A couple months into it, we just realized this isn't working for us. There's nothing wrong with that. I think that's something that you need to make sure you give yourself grace, and you need to make sure the people you work with understand, because again, you're finding your partnership.
TRUSTING YOUR GUT: FORCE VS. FLOW
Kelsey: For me, it's trust your gut, listen to yourself. Something I talk about a lot is force versus flow. If it feels like you're forcing it, if you have to chase somebody down for something, most likely that's how the relationship will be if you're running your own business and providing a service.
Instead, if it's a flow where it feels like natural conversations, where it feels like you're having fun and enjoying and also pushing each other to do better, then I feel like that's the green flag—this is the one you want to go for.
That was definitely a learning experience. Because of that, I've had a couple prospects that I've met, and it just felt forced. I had one person who was hunting me down, and they got my phone number. I was thinking, how did you find my phone number? I was on a vacation, and they just wouldn't stop calling me. I finally said, yes, let's just talk. At the end of it, I was thinking, this is not going to be a good match because I'm going to have boundaries. If they're not being followed right now while I'm on vacation, and I've been very vocal about that, I don't think I want to bring that into where I am now. I think because of what I learned with that previous client, it allowed me to step forward and say, sorry, this isn't going to work. If I have somebody I can recommend, I will. I will never try to leave somebody high and dry. But it really helped me evolve my decisions.
AJ: Did you have a moment of, should I really do this with that particular client when you were on vacation? What if this is the last time I ever get a project? Did you ever have that feeling?
Kelsey: With the one that found my phone number? I did. I was thinking, oh man. And then I thought, you know what? No. There's a reason for everything. If I'm feeling like—I can't remember, my coach talks about it—if you're feeling like you're crunching instead of feeling expansive, that's a sign. I thought, if I'm stressing out over this now, it's just going to continue, and I don't want to feel like I'm closed, and I don't want to bring that into my home.
I definitely had that moment. I was thinking, oh man, but then, no, we're safe. We have our baseline, bills are being paid, we're safe. It's okay.
AJ: I love how you talk through, you know, that part of your brain that's freaking out, and you're talking that part of your brain off the ledge. It's okay.
Kelsey: We're allowed to be scared! Let's walk through it.
AJ: I love the force versus flow. The forced relationships create resistance, flow feels natural.
Kelsey: It does. I think the more you're aware of how you feel when you work with certain clients—if there are people you enjoy talking to on the phone, take note of that. What about that relationship? What you're doing for them? What makes you feel good? Because that's what we should be focusing on bringing more of.
AJ: You mentioned the term emotional intelligence. That strikes me that it's really that. It's being aware of how we're feeling and how we're reacting to certain people in certain situations, and honoring that. So often, I know for years, I didn't honor that. I felt like I probably was like Spock—it was not logical, I couldn't explain that touchy-feely, squishy, emotional thing. Therefore, I completely negated it or ignored it.
Kelsey: And then you probably had so many clients that were draining your energy.
AJ: Yes!
Kelsey: And you were thinking, why am I so tired at the end of the day? That's emotional intelligence—you're not listening to your gut. It's telling you something, but you didn't want to listen to it because you thought you shouldn't do this. But it's a guiding force for you. Listen to it!
BUILDING RETAINER RELATIONSHIPS AND PREDICTABLE REVENUE
AJ: So that brings me to the question of, how much of your business is project-based and how much of it is retainer-based?
Kelsey: Right now, I'm at 90% retainer.
AJ: Wow!
Kelsey: I try to only do 10% project work, and what I mean by that is I won't do less than six months. I've been burned on this. I did a three-month contract, and I thought, you know what, this is going great. And they said, oh, it is, thank you! And then they just exited. I was thinking, this is a three-month contract, but I thought there was a relationship we were building for potentially something longer.
I was frustrated. I was like, that's my bad, I didn't set the expectation of what could follow. So now I do a minimum of six months because it takes about three months to really know somebody's business, understand their operations. Six months is where you start to see what works, what doesn't work. In my contracts, I put a minimum of six months up front and then monthly rolling after that with 30 days' notice. That way, if I want out, I can get out. If they want out, they can get out. It's not this messy goodbye where we're stuck in a six-month, year, or two-year contract that doesn't feel right.
I was trying to save myself a little bit. I didn't want to over-commit upfront and have them be unhappy that I locked them into something. But at the same time, you're vetting the relationship.
AJ: So for six months, that's your minimum, and then is it a monthly retainer that they pay?
Kelsey: Yeah, it's a monthly retainer. Usually, it's paid on the first of every month. We get that kind of rolling and flowing. It depends. I have some where I'll meet with them weekly, I have some that are twice a week, some that are once a month. Everybody's different because I'm building the relationship based off of what they need. Some people don't need an integration or fractional COO—they just need a sounding board every once in a while. Every couple of weeks, they're thinking, I'm struggling with this, let's just work through this, and go. Some people need, hey, I want you to run meetings with my team and make sure they're following through.
It depends. I really do customize. I tried to be like, I'm just going to do packages! It'll be $5,000 a month, $10,000 a month, $2,500! And I'm thinking, that doesn't work for what I do.
AJ: Everybody's different.
Kelsey: Everybody's different. I would get frustrated talking to people, and they'd be like, well, I only need this. And I'm like, I'm trying to fit a square peg in a round hole. I kept trying to do what I thought I should do. Now I just have one-on-ones with them. We talk it out. What does that look like? What are your goals? What are your objectives? Then I go away, I build the agreement, send it to them, and we sign.
AJ: Perfect. Do you find that the retainer gives people access to you whenever they need access to you?
Kelsey: It depends. Some of them, yes. I've been very clear about, hey, I'm not a 24/7 thing. If you need me and it's emergency, that's a different story. But the majority of the time, if you text me after 5:00 PM, my phone turns off notifications at that time. You'll get me between 9:00 and 5:00. I'm very strict about this, just because I want to make sure I'm present at home. It's just a boundary I set. Most of my clients know this. When we first kick off, they'll sometimes forget, but then they're like, oh yeah, that's right. And then it's normalized.
Once it becomes a culture thing, it's fine. You set the tone for what you want. I don't have to be available all the time. I've seen people that do that. They get burnt out, they feel overwhelmed. I didn't want to be that.
AJ: That was going to be my follow-up question. You said at the very beginning when you got into self-employment, you were taking on too many clients, saying yes to everybody. Have you experienced burnout?
Kelsey: I didn't experience burnout. I experienced being frustrated because I was working with people that were just sucking my energy. I would get off a meeting with somebody that I'd really enjoy, and then I'd go into one where I'm like, oh, I've got to do this. And I'd notice that—I was very aware of it. I was like, I'm frustrated, this person just sucked my soul. I'd go into the next meeting, and I wouldn't want to do that to them.
I always had to prep myself to be like, okay, reset. That was that client, that's fine. I'm grateful I have that relationship. Let's just learn from it. Now I'm getting ready for the next one. Let me go walk outside for 10 minutes, reset my brain, listen to some music, whatever it is. I had to take care of myself to show up better for the next person. That's when I was like, this is not sustainable. If I'm doing this every day, I'm going to get burnt out.
So I made a shift of, who do I want to keep, who do I want to let go? How do I support them if I'm going to let them go? I don't want to leave them high and dry. I gave them the remainder of the contract, and at the end of the year, I said, hey, I really appreciate the relationship. I gave them 90 days' notice and said, here are some people I'd recommend for you. That's how I shifted.
DELEGATION AND TEAM BUILDING
AJ: Now, you run your business by yourself, or do you have a team supporting you?
Kelsey: I have a team supporting me! I could not do what I do without some support. I have somebody who supports me with my social media posting. I have somebody who helps me run podcast interviews when I'm a guest on somebody's show. I have somebody that also does my client notes. There are some clients where I'm like, I don't want to be taking notes, I want to be present. I want to be listening, and not worrying about writing things down or doing it afterwards. So I have somebody who joins the meeting, listens to it, and does my meeting notes for me. It's helped so much!
AJ: That's brilliant. How did you come to the decision that you needed people to help you?
Kelsey: I think it was because I was spending so much time scheduling things, rescheduling things, doing calendar invites, logging into Canva. I'm not a graphic designer. I was spending hours because I wanted my social media to look good. I wanted to put my work out there. But then I was like, this is… if I'm spending a lot of time doing stuff like this, I'm not spending my time on revenue-generating things. I'm not spending my time on the 80/20. 80% of my time should be on revenue generation, supporting the people I have so they renew. 20% should be spent on admin, social media, those things.
I was doing it backwards. I was spending the majority of my time on admin, on my social media, on all these little things, trying to get new clients. But I wasn't focusing on my current clients and their experience. So I was like, what can I get off my plate?
What I did was, I actually audited my time. I did a week where I wrote down everything I did and how long it took me. At the end of the week, I went through it all and highlighted what I really enjoyed doing—what really filled my cup, what I would stay up until midnight working on because I thought, this is fun, I could do this forever. That's green. Yellow is stuff that I don't love, but I don't hate—it's neutral. Then red is, I don't want to do this anymore, this drains me.
I looked at it, and 60-70% of my time was in that red and yellow zone. I was like, this has got to go. What can I automate? What can I delegate? What can I delete? I just went down the list and thought, social media—I can delegate that. Can I delete it? No, because I feel like I should have it as my presence. Can I automate it? Potentially, but I don't think that's me. Can I delegate it? Yes! So I delegated it.
Scheduling—I was going back and forth so many times via email. I thought, I can automate this. Calendly, let's go! Now people just schedule themselves. Those were two big ones for me that really opened up time.
SYSTEMS AND FRAMEWORKS
AJ: So when you work with clients, is that the kind of thing you help them with?
Kelsey: Yeah, exactly. I help them look at, what are you doing? Where's your time going? What's taking up a lot of mental capacity for you? I really love the frameworks 10-80-10 and 1-3-1.
AJ: Ooh, tell me about those!
Kelsey: 10-80-10 is when you give a project to somebody and you meet with them. You spend 10% of your time, maybe an hour call with them, where you talk about the objective, the deliverable, what you're hoping for, the definition of done. They go away, they spend 80% of their time working on whatever you asked them to do. They come back, you spend 10% reviewing it with them, giving them feedback, iterating, pivoting, making changes. They spend another 80% working on finalizing things. They come back with the final 10%, and you review it together.
It's really about empowering your team to make decisions, ask questions, be owners of what they're doing instead of micromanaging them. I find a lot of my clients are like, I need to be in every single decision. I'm like, no you don't. You need to trust your team. You hired them because they're competent. Give them the space to be competent.
AJ: I love it. What's the other one?
Kelsey: 1-3-1. For this, if you have a problem—say, we need a CRM, or we have a CRM and we don't really like it, we need to get a new one—you meet with the person, talk about all the things you want your CRM to do. You give them the definition of the project, the scope of work, your wish list, want list. The definition of done is, I want you to come to me with maybe three recommendations.
They build that for you. They take what they think, and they come back with, okay, these are the options we have here. Which one would you go with based off our conversation, our budget, whatever you discussed? Let's talk about that. Let's start implementing that. It's really a project implementer system setup, but you can apply that to so many things. Like, our communication stinks, we're all texting and using WhatsApp and email and Slack, we're all over the place. Come together with a solution, one item, and let's test it. Let's go, and let them own it.
AJ: I want to go back and review them again. So it's 10-80-10.
Kelsey: Yep, 10-80-10.
AJ: Explain that again.
Kelsey: Perfect example: I have a social media person, her name is Eileen, I love her. We do brainstorming—10%. We have one call a month where we just do a 90-minute brainstorming recap of data, talk about what we want to do for the next couple months. She goes and she builds it. She comes up with the ideas. I sometimes get a crazy idea at 9 o'clock at night from Instagram, and I'll send it to her. But the majority of the time, she's implementing everything. She's creating, she's taking my vision and making it better because it takes me hours in Canva to do things. Not for her.
Then we come back together. She usually sends me everything. When we first started, I would record a Loom, log into her design, and say, hey, want to change this? This is why. I would actively change things and talk out loud to tell her the reasoning behind it so that when she'd watch the video, she'd understand. Oh, okay, so Kelsey really does not like this font, I've got to stop using it. This is what she's looking for, so she's learning the way that I think in real time.
Now we're to the point where I would even say we're at 5-90-5. I don't really send her Looms anymore. I'll just send her a quick note: hey, I changed this word, or hey, I didn't really like that photo, I like this one. That's about it. It's really gotten to that point over—it'll be a year this November—where I trust her. She knows where I want to go, she knows my vision. This is a great team.
AJ: And then the 1-3-1.
Kelsey: 1-3-1. So if you have a problem, trying to think… okay, hey, we need a CRM. Or no, we have a CRM, we don't really like our CRM. We need to get a new one. Go look into it. Perfect. You meet with them, you talk about all the things you want your CRM to do. You need to have, you're nice to have, I don't want to deal with this. Give them the definition of the project, the scope of the work, your wish list, want list. The definition of done: I want you to come to me with maybe three recommendations.
They build that for you. They take what they think, and they have, okay, these are the options we have here. Which one would you go with based off of our conversation, our budget, whatever you guys discussed? Let's talk about that. Let's start implementing that. Again, that's really a project implementer system setup, but you can apply that to so many things. Like, hey, our communication stinks, we're all texting and using WhatsApp and email and Slack, we're all over the place. Come together with a solution, one item, and let's test it. Let's go, and let them own it.
FUTURE VISION: ADVISORY, PODCAST, AND COMMUNITY
AJ: I want to switch gears a little bit and do some future thinking. Where do you want your business to be in 3 to 5 years?
Kelsey: Three to five years. What year is it? 2025? So is that 2028? That's crazy. Three years from now, I want to be at the point where my operations clients—I have a little and mighty team that help run their show. So I'm not as heavily involved. I'm at a higher level, strategic level with them.
I see myself having, I want to say, about 10 clients within my advisory, which is my—I call it coaching with your sleeves rolled up kind of thing. It's advisory because I'm working with the owner and with the team, helping them make moves in the business because everything just can't fall on the owner. So helping their leadership team push things through. Having about 10 people in there, and then, honestly, I've been thinking about podcasts and a group program.
The group program would be similar—I have a coach, Dan Martell, I love him, and I love his setup where he has four calls a month and many people that join his program. He does a teaching for the first 30 minutes and the last hour is answering questions. You learn by listening, but you also learn by listening to other people and what their challenges are and how they're leveraging his expertise and their expertise. What's caught, not taught, is what he always says. What you're catching in these calls are your takeaways.
I love that idea of having something like that for people that are thinking, hey, I need to get my operations together, I really just need a small and mighty community where we can talk operations, change management, leadership, and just general Q&A. Maybe guest speakers, like having an attorney because people can get scared about having to do that stuff. Just really opening it up and having these weekly sessions with people.
AJ: So a membership program.
Kelsey: Yep, it would be a membership program, at least a call a week, about one hour to 90 minutes, if not every other week, depending on my bandwidth too. Really having that sounding board for people where they can come, and it's not just me talking. I may even say, hey, AJ, you know, this is your area of expertise, what do you think? Helping build that community for people.
AJ: It's a great vision. How far out in the future is that?
Kelsey: I'm going to go with a year because I want to do the podcast first. This one I've been pushing off—no, I'm not ready, I'm not ready. But instead, I'm thinking, okay, let's just rip off the Band-Aid because whatever I do for my first episode, it's going to be different at episode 50, so might as well just rip off the Band-Aid and do it now and just start.
AJ: Yeah. So a group membership coaching program and a podcast. What stands in the way? What obstacles do you anticipate you're going to run into?
Kelsey: My own over-analyzing situation, for sure. I'm working through it. That, and not knowing how to do it yet. I kind of put together an outline based off of what I'm aware of, but I'm thinking, okay, cool, how do I get something that's on Riverside out there? How do I do these things? This is not my area of expertise. I don't need to know everything, but I need to know the how so that when I bring on somebody, I can ask the right questions too.
I'm just kind of chipping away at that because it's the end of Q3, holidays are coming. This would be cool to launch in the new year and just start building it now.
RAPID-FIRE QUESTIONS
AJ: Now I want to end with a couple—I call them the rapid-fire wrap-up questions. First question: what book, resource, or podcast has been the most valuable to you in your consulting career?
Kelsey: That's a good one. Podcast, I use Dan Martell's extensively. I really enjoy his. Oh, you know what? Book! I just almost forgot. The book that actually kind of helped me reposition my approach was Who Not How.
AJ: Who Not How?
Kelsey: Who Not How. Because I'm very much, how am I going to do it? What are the steps? I'm a list maker, I know what goes in the bags, I'm organized. I very quickly will go to, okay, how are we going to do that? What's that going to look like? How's this timeline going to work? Let's work backwards.
But it's helped me shift—not how, but who? Who do we know that can maybe help us make our starting point a little bit better? Who do we know that can help us do this instead of me trying to go figure out how to build a website?
AJ: Oh, I love it. That sounds like good advice for me because I tend to be the dig in and I'll figure it out myself. But there are a lot of other people that could help.
Kelsey: So Dan Martell's Podcast and Who Not How.
AJ: Second question: what's one piece of advice that you wish you'd had at the beginning?
Kelsey: Overthinking it. Yeah, just stop overthinking it. Do it scared. It's going to be okay. Everything works out the way it's supposed to. Sometimes you just have to go for it.
It took me a little while to get there, and it was very much like, hey, if business fails tomorrow, I'm still going to be ahead because I have all these learnings that I've already gone through. You're not starting from zero. I think reminding yourself of that. I can always go back to corporate. It's there. It's not going away.
AJ: Yeah, takes the fear away.
Kelsey: It does. It's like, hey, there are options. People may make you think, no, you should be scared, oh, the economy's tanking, or whatever's happening. But you're going to be okay. If you trust yourself, you're going to be okay.
AJ: Excellent. And now this is the most important question. How do people find out about you and your work?
Kelsey: I'm on Instagram, so it's at KelseyDaingerfield.com, or Kelsey Daingerfield. Daingerfield is D-A-I-N, so there is an I in there. But that's where you can find me, that's where I hang out the most. I find the other ones, I just kind of get sidetracked. I have a 3-year-old and a 7-year-old, so I'm not always on anything else besides maybe Instagram. So that's where you can find me.
AJ: Okay, wonderful. Well, Kelsey, thank you so much for being my guest today. I really loved our interview, and you came up with some great tidbits that I know the listeners will be able to apply in their businesses and lives. So thank you so much.
Kelsey: Thank you!
