Design Your Business · 2026-06-01 · 10 min
Key moments - from our scoring
Substance score
27 / 100
Five dimensions, 20 points each
Jen Taylor, a certified operational expert and former luxury wedding planner, cuts through the myth that hiring is only for big businesses. She identifies four clear signs you're ready to hire: turning away revenue because you're maxed out, doing tasks someone else could handle at 80% proficiency, feeling exhausted despite stagnant revenue growth, and avoiding growth due to capacity fears. Taylor reframes hiring as a profit decision, not an expense - if a $25/hour hire frees you to sell $5,000 in packages, that's leverage. She covers multiple entry points: virtual assistants, social media managers, online business managers, and wedding day assistants, sharing her own experience starting with a bookkeeper because she disliked numbers. The episode addresses common fears ("it's easier to do it myself," payment concerns) and offers practical structures: start small with contract-based, per-event, or project-based arrangements before expanding. Taylor emphasizes the CEO work required upfront - writing job descriptions, creating flowcharts, and documenting standard operating procedures - so hires have clear direction from day one.
Turning away revenue because you're maxed out; doing tasks someone else could handle at 80% proficiency instead of your 60%; feeling exhausted while revenue stagnates; and avoiding growth because you fear capacity constraints.
Yes - Jen Taylor considers outsourcing and offboarding work (bookkeeping, social media, email, admin tasks) as hiring because someone else is doing work you don't want to do or don't excel at, freeing you to focus on higher-value activities.
Start small with contract-based, per-event, or project-based arrangements rather than full-time roles. Taylor recommends getting paid monthly so you can pay staff from those deposits, and suggests talking to your bookkeeper or accountant to find a structure that works for your cash cycle.
Write job descriptions, create organizational flowcharts showing where each person fits, and document standard operating procedures and workflows so new hires understand what success looks like in their role and know where to turn with questions.
It's a profit decision - if paying someone $25/hour frees you to sell $5,000 worth of packages, that's leverage and you're making money on the hire, not just spending money.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode cycles through well-worn small-business hiring basics (signs of overload, first hire types, fear of payroll) with very little non-obvious content. The one modestly useful frame - treating a hire as a revenue-leverage decision rather than a cost - is underdeveloped and presented in passing.
it's a profit decision, not an expense decision. So if hiring somebody at $25 an hour frees you up to sell $5,000 worth of packages, that's leverage
You're doing tasks someone else could do at 80% proficiency versus 60%
Every idea here - delegate what you're bad at, start with a VA or bookkeeper, contract before committing to salary - is standard small-business advice repeated endlessly across the genre. There is no contrarian framing, no first-principles thinking, and no fresh angle on the hiring question.
you don't want to do the stuff that you suck at
Start small. Make it a contract base, make it per event, make it project based
This is a solo episode from a host who is a former luxury wedding planner turned business coach - a relevant practitioner for the niche but not at notable scale. Her hiring story is told as an organic, unplanned accident rather than a repeatable system, which limits the instructional value of her credential.
it kind of happened organically and very. It wasn't intentional, but it was lovely
I did a wedding, it was in November. And I realized at that moment that I needed to have somebody with me
There are a couple of concrete numbers ($25/hour, $5,000 package, paying by the 5th of the month) that anchor the advice slightly, but the overall episode is dominated by vague personal anecdote and abstract encouragement rather than named companies, verified data, or measurable outcomes.
if hiring somebody at $25 an hour frees you up to sell $5,000 worth of packages
they got a percentage of the wedding. So if they did the wedding and we get paid on the first of the month, I'm able to by the fifth, give them a check
This is an unstructured solo monologue with no interviewer, no external challenge, and no follow-up pressure. The host frequently trails off, contradicts herself mid-sentence, and acknowledges she 'did it by the seat of her pants,' leaving most claims unchallenged and underdeveloped.
I'm probably not the one to talk to about this because it kind of happened organically
I kind of, I won't kind of. I did it by the seat of my pants
Computed from the transcript - who did the talking, and the words that came up most.
In this episode, I’m diving into one of the biggest mindset and growth hurdles business owners face: hiring before you feel completely ready. I’m sharing the real signs that it’s time to outsource, what tasks you should stop doing first, and how hiring can actually become a profit decision instead of an expense. We talk through the fears that keep so many entrepreneurs stuck, from worrying no one will do it like you to wondering if you’ll consistently be able to pay someone. Topics covered in this episode include: The hidden sign that proves you may already be overdue for help Why “doing it yourself” could actually be costing you money The surprising first hire that changed everything for me How to know which tasks you should stop touching immediately I would love to connect on Facebook: & Instagram: ! Resources Mentioned: Small Business Task Appendix: Show notes available at:
Transcribed and scored by The B2B Podcast Index.
Narrator: Feeling overwhelmed every time you sit down at your desk or pull that pile of papers onto the couch to work on your business, Are you drained of the energy because you hate managing the operational details? You are the visionary, the creator, the
Jen Taylor: heart and soul behind your passion.
Narrator: You thrive on doing what you love, and that's why you started this journey. You're great at envisioning the big picture, but get, uh, bogged down by the nitty gritty can be a drag. Right? Here's where I can step in. Imagine having someone who can be that steady voice and steady force in your life, keeping you accountable and aligned with your vision to ensure those big dreams get attained. That's exactly why I'm offering a free operational audit. Let's spend an hour together where I can help you gain crystal clear clarity on the results that you want to achieve in your business and your life. Let's turn your dreams into into plans and your plans into reality. Join me on this journey.
Jen Taylor: Welcome to the Design youn Wedding Business Podcast. The podcast for wedding professionals and creative entrepreneurs ready to build a business that is as intentional as the experiences they create. I'm Jen Taylor, business coach, system strategist,
Jen Taylor: and former luxury wedding planner turned certified operational expert.
Jen Taylor: I help business owners like you get
Jen Taylor: out of the weeds, own your CEO
Jen Taylor: role, and build a business that supports
Jen Taylor: your life, not the other way around.
Jen Taylor: Each episode, we'll dive into strategies, systems, and mindset shifts that bring clarity, momentum, and sustainable success.
Jen Taylor: So grab your favorite beverage, get comfy,
Jen Taylor: and let's design a business that you're excited to wake up to.
Jen Taylor: Hello, Jen Taylor, Design your Wedding Business Podcast. I am your host. If you ever thought I can't afford help, why simultaneously drowning in work. This episode is for you. Hiring isn't about being big. It's about being sustainable. So let's talk about when to hire, who to hire, and how to do it without panic. So signs you're ready to hire.
Narrator: 1.
Jen Taylor: You're turning away revenue because you're maxed out. 3. You're doing tasks someone else could do at 80% proficiency versus 60%. 3. You're exhausted, but revenue isn't growing. 4. You avoid growth because you fear capacity. And higher is also like you're looking at hiring somebody do the books. You're hiring somebody to help you with social media. You're hiring somebody to take some of the admin tasks off of your daily to do list. This is also hiring. It's offboarding. You're outsourcing. Outsourcing is a better term, but there's somebody that is doing the work for you. And I consider that hiring as well, because you don't want to do the stuff that you suck at. Like, that was the first thing I hired was somebody to do the books, because I don't like doing books. I'm one to avoid numbers, but it forced me to. To do that. I'm somebody who is off and on. On social media. I'd like to have somebody do it, but then I get concerned that it's not my voice, and then I get all weird. But I know I can do some of my own and have somebody else do some of it as well and be okay with that because they have better ideas. This is what they do. This is what they're proficient at. I am not. You have somebody do your email or write your newsletters or you're using AI to help you with things. Those are all okay. And those are things that can help alleviate. But when you start talking about hiring an assistant or hiring somebody, uh, to help plan, like, I'm. I'm probably not the one to talk to about this because it kind of happened organically and very. It wasn't intentional, but it was lovely. My senior planner moved over from other part of the state, and everybody told her to come talk to me. I'm like, she met me at a networking event and we talked and we chatted and I said, let's meet up after, you know, after this. Not necessarily right after, but a couple days later. And we talked about it, you know, like, she had the chops to do her own, you know, but she wanted to work for somebody and then slowly get out of her day job. Okay, let's figure out how this works. So I did. So it's a profit decision, not an expense decision. So if hiring somebody at, uh, $25 an hour frees you up to sell $5,000 worth of packages, that's leverage. You're making money on that. So look at it that way. And I, you know, and I was creative on how I paid them and
Narrator: what they, you know, what they did.
Jen Taylor: And looking back, I probably still would have done some of it the same, and some of it I would have done differently. But, you know, it was that. And then the rest of them just came on in different roles at different times. And all of a sudden I had a great team. So it's going to work differently for everybody. But your first hire options. I talked about it. Virtual assistant, social media manager, an online business manager, a wedding day assistant. That was the first hire. I mean, she wasn't it was one of. I was doing everything on the wedding day. I had no assistant, I had no nothing. And I went to, I did a wedding, it was in November. And I realized at that moment that I needed to have somebody with me on the day because I cannot do it all. And so bringing somebody on just for the day, just for the assistance, and that was great. And then, you know, I already had the bookkeeper. I had, as I said, social media person, off and on. I've never had a virtual assistant. I'm pretty organized with that. So then eventually I hired an, uh, associate planner, or she was my senior planner and I had associates under her. So just start thinking that, start creating that. Where, you know, you see your job where everybody is who you are in the flow of the jobs. But the fears are, no one will like you. What if I can't pay them? It's easier to do it myself. Number three is probably the biggest one. It's easier to do it myself. And then the second one is, what if I can't pay them? And that's a big fear. I mean, I, believe me, I had a big fear around that. So this is where getting paid monthly helps, because they got, you know, they got a percentage of the wedding. So if they did the wedding and we get paid on the first of the month, I'm able to by the fifth, give them a check for their weddings and do all the things around it. So, you know, you find a way. Talk to your bookkeeper, talk to your accountant. They're going to help as well. I kind of, I won't kind of. I did it by the seat of my pants. So start small. Make it a contract base, make it per event, make it project based. That's what I, I made it per event. And then if they did something extra and things like that, it was a project base. So you figure out what that looks like and you're testing it before you're expanding out. So really sit down and write down. I would actually go back and look at your CEO day and write down the three tasks in each of these areas that you don't want to be doing anymore. So look at the lead tracking or reviewing the pipeline or your marketing or your calendar audit. Look at those things. Look at what you're doing every day that you don't want to do. Do you want to expand your business? Then what does that look like? How does that look? And write those things down. Start writing down job descriptions to really get going. You write down the job description of the person you want to hire, do you want to hire that virtual assistant or that social media or that business manager? And then if you want to bring on a day of assistant, what does that look like? What does that look like for the wedding weekend? Is that person there on Friday and Saturday and Sunday, or are they just there on the day of the wedding or the day of the event? So start thinking a bit about it in the things that you don't want to do, the things that you suck at, and go from there, because that's the easiest way to start thinking. So think about, you know, how you want the business, how do you want your business structured? You're the CEO or you're the business owner. Do you want, you know, and then start doing the flowchart of who's working where and really start creating that and then the job descriptions for those people. And this is part of your CEO time too. So think about it. Like, if you want to start doing this, you have to start thinking about the CEO time because that's they're going to be looking towards you for questions. And your CEO time better be creating that standard operating procedure, that workflow. What do they need to do for their business for their job to be successful? And you have to have all that in place before you start hiring. So your call to action is write down three tasks you should not be doing anymore as a business owner. Okay, Have a good day.
Jen Taylor: Bye. If today's episode sparked an idea or gave you a nudge you needed, I'd love to hear about it. DM me on Instagram En Taylor Consulting or leave a review to help more wedding pros find this show. And if you're ready for the next level clarity and support, head over to jenntaylorconsulting.com to book your free business on it. Until next time, stay focused, stay intentional, and keep designing a business that works for you.
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