One of the hardest lessons I learned in my early years wasn’t about planning — it was about investing wisely.

I know how overwhelming it can feel to decide where to put your money when you’re growing your wedding planning business.

And looking back, there are choices I’m so grateful I made early, and a few I wish I could redo.

So today, I want to share the truth about both the best investments and worst investments I made in my early days.

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Welcome back to The Planner’s Edit. I’m Desirée Adams — wedding planner, designer, business owner, creative strategist, and your guide to building a more intentional, elevated, and fulfilling business in this industry we love.

In our last episode, we talked about the things I wish I had done sooner in my planning business — the support, clarity, and structure that would have changed everything had I implemented them way earlier.

But today, I want to zoom in even closer.

Because while hindsight shows you what you should have done sooner, it also shows you something else: the best investments that truly moved the needle… and the ones that didn’t. And when you’re building a wedding business, knowing the difference can save you years of frustration, and thousands of dollars.

So in this episode, I’m sharing the honest truth about the best investments I made early that paid off, the ones that accelerated my growth, and the ones that, if I could go back, I’d rethink entirely.

Let’s dive in.

1: Joined A Wedding Planner Intensive To Map Out All My Planning Systems

One of the very first investments I made in my business — and one of the earliest investments that actually paid off — was joining a wedding planner intensive specifically focused on mapping out my systems.

And I’ll be honest: at the time, it felt huge. It felt scary. And I asked myself way too many times, “Who am I to spend money on something like this?”

But looking back, this was one of the smartest decisions I ever made. Not because I didn’t know how to plan a wedding — I did. But because I didn’t yet understand how to turn what I knew into a repeatable, scalable, client-ready process.

What that intensive gave me was structure. It gave me a blueprint, and a way to turn the chaos in my head into a smooth, polished client experience.

And here’s why that mattered so much:

It Forced Me to Work On My Business, Not Just In It

When you’re new — and honestly, even when you’re seasoned — it is so easy to operate in reaction mode. You answer emails as they come in, you update timelines as needed, you create documents only when a client asks for something.

But that intensive pulled me out of survival mode.

It required me to step back, zoom out, and actually build the workflows, documents, and processes that would carry me forward. Instead of reinventing the wheel every time, I finally had a foundation under me.

It Helped Me See My Business as a System — Not Just a Service

Before joining an intensive, my processes lived entirely in my head. I “knew” what to do… but nothing was written out. Nothing was templated or automated.

Which meant:

• I couldn’t delegate.
• I couldn’t scale.
• I couldn’t lead.
• And I definitely couldn’t maintain consistency across clients.

The intensive showed me how to turn planning into a system — from inquiry to final walkthrough. And once I had a system, everything felt easier, clearer, and way more professional.

It Helped Me Elevate My Client Experience Long Before I Felt ‘Ready’

This was one of the biggest surprises.

I walked into that intensive thinking I would learn “backend business stuff,” but what I learned was how to create a client experience that truly felt luxury… even before I had booked luxury clients.

It helped me understand how to:

• communicate proactively
• create polished touchpoints
• build trust early
• guide clients confidently
• And stay organized without feeling overwhelmed

I didn’t know it then, but this is what future clients would hire me for.

It Fast-Tracked My Growth by Years

Could I have figured out my systems eventually? Yes.
Would it have taken me three times longer and a lot more stress? Also yes.

We don’t talk enough about the cost of not investing.
The cost of doing everything manually, of looking unpolished, of being inconsistent, and the cost of burnout.

That intensive gave me a foundation that allowed every future investment — my VA, my assistants, my content creator, my brand designer — to work better, because they had something structured to plug into.

It paid off not just in time saved, but in confidence gained, clients booked, and clarity created.

Once I saw what having structured systems could do for my business, it completely shifted how I thought about support and growth. And that brings me to another one of the best investments that changed everything for me early on: hiring a coach.

2: Hired a Coach

To be clear, I did not hire a coach because I didn’t know how to plan weddings. I hired a coach because I didn’t know how to grow a business.

There’s a massive difference.

When you’re building a wedding business, you are making decisions you’ve never made before. Decisions around: 

• Pricing.
• Boundaries. 
• Branding. 
• Services. 
• Systems. 
• Client experience. 
• Marketing. 
• Scaling. 
• Leadership. 

It’s a lot.

And for a long time, I tried to navigate all of it alone. I pieced together advice, searched for answers late at night, and second-guessed myself constantly.

But hiring a coach changed that instantly.

A Coach Gives You Clarity Much Faster Than Trial and Error Ever Will

One of the most valuable things a coach gave me was clarity — clarity on what matters, what doesn’t, what I should focus on, and what I needed to let go of.

Instead of spending months wondering:

• “Is my pricing right?”
• “Should I offer this service?”
• “Why am I attracting the wrong clients?”
• “Is this boundary reasonable?”

…I had someone who could look at my business objectively and say: “This is the next right step.”

That clarity alone accelerated my growth.

A Coach Helps You Build the Business You Want

Without guidance, it’s easy to build a business based on what you think you’re supposed to do. You replicate offers you’ve seen, you follow trends, and you mimic what other planners are doing.

A coach helped me define my way of doing things.
My strengths, values, long-term vision, and ideal clients.

And once I understood those pieces, everything about my business became more aligned, and more successful.

A Coach You Accountable to the Version of You That You’re Becoming

There’s something powerful about having someone in your corner who refuses to let you play small.

Someone who will say:

• “You have to raise your prices.”
• “Protect your boundaries.”
• “Stop discounting your expertise.”
• “Quit offering services you hate.”
• “You are ready for this.”

The accountability piece alone made this one of my best investments.

By Hiring a Coach Early, I Was Able to Avoid Years of Mistakes

So many of the decisions planners struggle with for years — I moved through them much faster because I had guidance. I didn’t waste time on misaligned clients. I didn’t cling to outdated services. And I didn’t underprice myself into burnout.

Hiring a coach helped me grow more confidently, more strategically, and with far less chaos.

And it’s one of the investments I would make again and again, without question.

Which brings me to another early investment that had a big impact on my growth and visibility — paying someone to blog for me.

3: Paid Someone to Blog For Me

Now, could I write? Yes.
But did I want to spend hours writing blog posts every month? Absolutely not.

And more importantly, blogging wasn’t something I did particularly well at that stage in my business. I could write captions, emails, timelines — but writing keyword-rich, strategic blog posts that actually ranked on Google? That was not my zone of genius.

But here’s what I did know: If I wanted to attract my ideal clients — clients who were planning thoughtfully, researching thoroughly, looking for something elevated — they were going to find me through search.

Blogging is one of the few marketing channels that works 24/7.

It doesn’t rely on an algorithm. They don’t disappear after 24 hours. It does build authority. And it brought in clients who were already aligned.

Hiring someone to blog for me meant the work actually got done — consistently, strategically, and at a level I wasn’t able to produce on my own while juggling clients.

And the payoff was huge. Blogs I had written years earlier continue to bring in inquiries, boost my SEO, and position me as a trusted expert in my market. Some of them performed better than anything I had posted on social media.

But the biggest ROI wasn’t just visibility — it was time. The hours I wasn’t spending researching keywords or writing long-form content became hours I could invest in serving clients, refining my process, designing better events, or focusing on higher-level CEO tasks.

It also taught me an important lesson early on: Just because you can do something doesn’t mean you should be the one doing it.

Blogging was a perfect example of a task that was essential to my business growth — but not essential for me to personally own. And outsourcing it early freed up space for me to build the parts of my business that truly needed my voice, my creativity, and my leadership.

And that same mindset carried into the next investment I made: bringing a virtual assistant into my business long before I felt fully ready.

4: Hired a VA

Now, you’ve heard me talk about this before, but in the context of the best investments, it deserves its own moment. Because this wasn’t just about “getting help.” It was the first time I realized that buying back my time was one of the smartest financial decisions I could make.

At that stage in my business, I was still doing everything myself: inbox, scheduling, follow-ups, checking contracts, updating client documents, posting to social media, fielding vendor questions… all while planning multiple events.

And even though I could handle it, it was costing me in ways I didn’t fully understand yet — costing me energy, costing me creativity, costing me the ability to take on more aligned clients.

Hiring a VA changed that almost immediately.

What surprised me wasn’t just the time savings. It was how much mental space I got back.

Suddenly the little tasks — the ones that pile up, distract you, and interrupt your workflow — weren’t on my plate anymore. And that gave me room to think bigger. To plan strategically. To show up more fully for my clients and my business.

It also made me more consistent. Emails went out in a timely manner. Onboarding was smoother. Follow-ups didn’t get buried during event weeks. Posting on social media wasn’t an afterthought.

All the invisible, unglamorous parts of running a wedding planning business… became easier. And because I wasn’t spending my days doing admin work, I actually had the energy to grow.

And here’s the other piece no one told me early on: Hiring support increases your confidence.

When you have someone backing you up, helping you stay organized, helping you maintain a polished client experience, you start showing up like the CEO of your business — not the bottleneck of it.

That confidence translated into better client calls, clearer boundaries, higher prices, and a stronger brand presence.

Hiring a VA wasn’t just a practical investment. It was a transformational one.

And it laid the groundwork for the next investment that dramatically elevated both my client experience and my capacity: hiring staff to help plan and support me on the wedding day.

5: Hired Staff to Help Plan / Day-Of Staff

Hiring day-of staff and planning support was another investment that paid off in ways I never could have predicted — not just financially, but in the quality of my events, the way I showed up as a leader, and the level of service my clients received.

And just like hiring a virtual assistant, this is something I wish I had done much, much earlier.

Support on the Wedding Day Makes Every Detail Smoother

When you don’t have staff, you end up wearing every hat — designer, coordinator, problem solver, stylist, therapist, timekeeper, setup crew… all at once. And the truth is, no planner can physically (or mentally) hold that level of responsibility without something slipping.

Bringing on day-of assistants transformed my weddings. Suddenly, the things I had been juggling alone were shared. Setup moved faster. Transitions were smoother. Vendors had someone else to communicate with. And I had the mental space to stay focused on the big picture instead of constantly putting out fires.

Clients may not always understand why their wedding felt seamless — but they absolutely feel the difference a team makes.

Having a Team Allows You to Finally Be the Lead Planner, Not the Labor

When you’re operating alone, you spend so much of your wedding day doing — lifting, moving, checking, running, troubleshooting — that you never actually get to lead.

But once I started bringing staff with me, everything changed.

I wasn’t the one tracking down missing boutonnieres, lighting 90 candles at the last minute, or adjusting chairs or fixing escort cards.

I was able to guide the event, direct vendors, focus on design execution, and be fully present for my couple. That shift doesn’t just elevate your events, it elevates your experience of executing them.

A Team Makes You More Professional in the Eyes of Clients and Vendors

One of the unexpected benefits of hiring support was how it changed the way people saw my business.

Clients saw that I had a team, which instantly communicated preparedness, organization, and professionalism.
Vendors saw that I wasn’t trying to do everything alone, which made collaborations smoother and built trust faster.

And I felt more confident walking into a wedding day knowing I wasn’t doing it all myself. That confidence translates into leadership. And leadership translates into better events.

Freeing Up Capacity for More and Better Clients

The biggest ROI wasn’t even necessarily “help on the wedding day.” It was the capacity it created.

Because once you’re not exhausted by every event…
Once you’re not recovering for three days afterward…
Once you’re not scrambling behind the scenes…

…you actually have room to take on more aligned clients, raise your prices, and scale sustainably.

Hiring help isn’t just about the wedding day. It’s about protecting your energy, your creativity, and your longevity in this industry.

Hiring Staff Helped Me Step Into the Business I Was Trying to Build

When I finally brought on assistants, I realized something important: I had been operating like a “one-woman show” long after my business had outgrown that model.

Having a team allowed me to step into the planner I was becoming — not the one I used to be.

And that shift in identity was foundational to elevating my brand, my client experience, and my future growth.

Which brings me to the next investment that made a massive difference in my business — and one that often gets overlooked: hiring a content creator.

6: Hired a Content Creator

Hiring a content creator was one of those investments I resisted for far too long — and looking back, it’s something I wish I had done much earlier. Not because I didn’t understand the importance of content (trust me, I did), but because I didn’t understand how much easier and more effective my marketing could be with someone supporting that side of my business.

Content Was Always Important — but Never My Priority

I knew social media mattered, and showing up consistently mattered. And I knew my ideal clients were watching.

But between planning, designing, emailing, managing vendors, managing clients, and everything else that fills a planner’s day… content was always the first thing to fall off my plate.

I would go weeks without posting. I had beautiful events, just no time to share them. Which made me get into a viscous cycle of starting strong and then disappearing during busy season. It wasn’t for lack of effort — it was for lack of bandwidth.

But, hiring a content creator changed that instantly.

They Helped Me Show Up Even When I Didn’t Have Time

The biggest gift a content creator gave me was consistency.

They helped me:

• repurpose content I already had
• turn galleries into reels, carousels, and story highlights
• They captured behind-the-scenes moments I never would’ve remembered to film
• And helped create a strategy instead of spur-of-the-moment posts

Suddenly my marketing wasn’t reactive, it was intentional.

I wasn’t showing up only when I had time. Finally, I was showing up regularly, in a polished, strategic way that reflected the level of service I offered.

I Was Able To Tell My Story in a Way I Couldn’t on My Own

Great content creators don’t just “post.” They translate your voice, your values, your creativity, and your client experience into visuals and messaging that resonate.

Because here’s the truth:Many planners are incredible at storytelling through events…
…but struggle to tell the story of their own business.

A content creator helped bridge that gap for me.
They helped me show clients:

• what makes my process different
• what I value
• what it feels like to work with me
• what kind of couples I’m best aligned with

And that clarity brought in better inquiries.

The ROI Was Measurable — In Bookings, Not Just Likes

This wasn’t an “Instagram experiment.” It was a strategic business investment.

Because once my content became consistent and aligned:

• my inquiries improved
• my booked clients improved
• my brand elevated
• my prices increased
• And my confidence grew

People weren’t finding me by accident anymore. They were finding me because my online presence reflected the work I was actually doing.

Hiring a Content Creator Gave Me Permission to Step Fully Into My Role as CEO

This was the part I didn’t expect.

Outsourcing content freed me from the pressure of “performing” online while juggling everything else behind the scenes. I could finally focus on planning, designing, leading, and delivering an exceptional client experience — while someone else helped amplify that experience.

It wasn’t just about content It was about alignment.
It was about showing up in a way that matched the business I was building.

And once I invested in a content creator, I finally felt like my brand and my reality were telling the same story.

Which brings me to another one of the best investments that supported that story — hiring a brand designer.

7: Hired a Brand Designer

Hiring a brand designer was one of the earliest investments that completely transformed how I showed up in my business — long before my business “felt big enough” to justify it. And I’ll be honest: at the time, it felt like a luxury. Something I could wait on. Something I’d “do later.”

But looking back, getting clear on my visual identity early on paid off in ways I didn’t expect.

A Cohesive Brand Helped Me Attract the Clients I Actually Wanted

Before working with a brand designer, my business looked like every other new planning business — Canva templates, trendy colors, and whatever fonts I thought were “pretty” at the moment.

And because of that,I attracted anyone and everyone.

But a brand designer helped me visually communicate:

• the level of service I offered
• the style of weddings I wanted
• the type of couples I aligned with
• the kind of experience I created

My brand finally matched the quality of my work. And that alignment changed the kind of inquiries I received almost immediately.

Your Visual Identity Shapes the Way People Experience Your Business

A brand isn’t just a logo or a color palette. It’s the tone, the feeling, the story your business communicates before you ever say a word.

When I invested in professional branding, I noticed:

• my website converted more inquiries
• my pricing conversations felt easier
• clients trusted me faster
• my proposals felt more elevated
• my social media presence felt consistent

My brand wasn’t just “pretty” anymore — it was strategic.

It supported my sales process.
It strengthened my positioning.
And it helped clients understand who I was before they ever met me.

And that clarity led to better, more aligned bookings.

The ROI Was Confidence — And Confidence Changes Everything

One of the most surprising benefits of hiring a brand designer was the way I started showing up differently.

Before branding, I was hesitant.
I downplayed my value.
I didn’t always feel like a “real” business.

But once my brand reflected the level of quality I was committed to, it helped me step into the planner I wanted to become.

It’s amazing how much easier it is to own your expertise when your brand supports it visually and emotionally.

Branding Is Not an Expense — It’s an Accelerator

When new planners hear “brand design,” they often think it’s a finishing touch. Something you do when everything else is in place.

But in reality, branding is a great starting point.

It influences:

• your messaging
• your website
• your portfolio
• your content
• your sales
• your systems
• your confidence
• your leadership

It touches every part of your business.

And it’s one of the investments that, in hindsight, I’m most grateful I made early — because it made every other investment work harder.

Which brings us to something important: not every investment pays off.
Some do. Some don’t.
And some… are just expensive lessons.

Let’s talk about the ones that didn’t pay off the way I hoped.

8: Investments That Didn’t Pay Off

Even if we don’t talk about them publicly every planner has investments that were a flop. And honestly, these are just as valuable as the investments that worked, because they teach you what not to repeat.

And for me, a few patterns showed up clearly.

I Bought Courses I Never Looked At

Listen… we’ve all done this.

I purchased bundles, summits, masterclasses, and massive digital libraries thinking, “This is going to change everything.”

But here’s what actually happened:

• The content was overwhelming.
• None of it was tailored to my business model.
• I didn’t have the time to implement any of it.
• And because it wasn’t personalized, I didn’t know where to start.

Most of those courses sat untouched.

Education only works when it’s aligned with your goals, your stage of business, and your capacity to implement — not when it’s a giant bundle that looks shiny and will “fix all your problems” in the moment.

I Also Bought Tools and Software I Didn’t Need Yet

Another mistake: buying platforms and tools because other planners swore by them… but I didn’t actually need them at the stage of business I was in.

I bought:

• softwares I didn’t have the clients to justify
• subscriptions I barely used
• tools I thought would “fix” my workflow
• systems that were too advanced for where I was

And while none of them were bad tools, they weren’t right for me at the time.

The biggest lesson here? Just because something works for another planner doesn’t mean it’s the right investment for your business right now.

I Bought Things I Thought I Needed to “Look” Professional

I bought things that made me feel like a planner — not things that actually made me a better planner. Things like:

• props for styled shoots
• décor items I thought I’d use one day
• gear I didn’t need
• supplies I imagined clients would expect

Most of them collected dust. You have to remember, professionalism doesn’t come from stuff. It comes from systems, communication, consistency, and leadership.

Making Purchases I Thought Would Be a Shortcut 

Some of my early investments didn’t pay off because I was buying things to fix problems I hadn’t actually defined yet. I was solving symptoms — not the root of my issues.

Buying tools won’t replace knowing your niche.
Purchasing courses won’t replace building your unique processes.
Investing in equipment won’t replace having a strategy.

The investments that didn’t work were the ones I made from fear, comparison, or scarcity — not from intention.

Before We Close

I want to leave you with this: building a successful wedding business isn’t about making perfect investments. It’s about learning which ones actually move you forward. The decisions that paid off for me early on weren’t the flashy ones — they were the ones that gave me structure, clarity, support, and space to grow.

And the investments that didn’t work weren’t failures. They were feedback. They helped me understand what I really needed, what I didn’t, and where my time and energy were better spent.

When you invest from intention — not comparison, fear, or scarcity — your business starts to feel lighter, more aligned, and far more sustainable. And your growth becomes so much faster because every decision is rooted in who you’re becoming.

If anything in today’s episode resonated with you, or if you’re rethinking the way you invest in your business moving forward, I’d love to hear what stood out. Come share your thoughts with me over on Instagram @plannersedit.

Turn Your Next Steps Into the Best Investments You’ve Ever Made

If listening today made you rethink how you invest in your wedding planning business — or helped you see where support, clarity, and structure could make a huge difference — I’d love to help you take those next steps with intention.

My mentorship and coaching program, Full-Service Foundations, is now open for enrollment with limited spots available for January 2026. I created this program because so many planners are working hard… but not always on the things that actually move their business forward. When you invest in the right systems, the right support, and the right strategy, everything changes — your confidence, your client experience, your pricing, and your long-term growth.

Inside the program, I walk you step by step through building a luxury-level full-service planning and design package, refining your process, and creating a business model that supports the kind of work you want to do and the kind of life you want to live. If you’re ready to invest in your business with clarity, not guesswork, and finally build the foundation that elevates everything you do, I’d love to support you.

You can enroll now at desireeadams.co/education.

Thank you, as always, for listening to The Planner’s Edit.

If you enjoyed today’s episode, please follow the show and leave a quick review — it helps other planners and creatives find us.Until next time, I’m Desirée Adams — and this is The Planner’s Edit.