I’m feeling sentimental as I record this because today marks my business birthday—eight years in business! It feels absolutely wild to say that out loud. So, to celebrate, I want to share eight overarching business lessons I’ve learned along the way. Some are things I’m glad I did early on, some are things I’d absolutely do differently, and others are simply key takeaways from my journey.
But first—what a ride it has been! I can’t believe I’m in year eight. When I say I started my wedding business on February 2, 2017, it’s because that’s when I officially launched. However, I don’t have a firm start date for The Kara Report because it started as a COVID pivot. When destination weddings were put on pause, I shifted my focus—and I ended up loving it so much that I never looked back.
I don’t talk about this often, but I truly loved planning weddings. I loved traveling to Mexico, working with brides, and creating unforgettable experiences. But it was also incredibly stressful. I don’t think I even realized how much stress I was under until I stepped away from it. The unpredictability—changing airline schedules, lost luggage, missed connections—so much of it was out of my control. And yet, people would still be upset, even when there was nothing I could do.
To everyone in the wedding industry listening: You are amazing. Truly. It’s a high-pressure job, and wedding professionals don’t get nearly enough credit for the incredible work they do. I will always believe that.
So, back to The Kara Report. Since it started as a pivot, it never really felt like I was starting from scratch. When I first launched my wedding business eight years ago, I simply made a post on Facebook announcing I was open for business—and from that moment on, my life changed.
Now, let’s dive into the eight biggest lessons I’ve learned.
Listen on Apple | Listen on Spotify
Table of Contents
I have to be honest—I’m not a big birthday person. My birthday is in October, and I barely talk about it. I don’t even know if I’ve ever made an Instagram post about it. Maybe I have, but it’s just not something I really celebrate in a big way. I might have cake with family or friends, but that’s about it.
That said, I do always make a point to celebrate my business birthday—at least I did in the first few years. Then, of course, life happened. Between COVID, having a baby, and everything else, things got in the way, and I wasn’t always able to mark the occasion the way I wanted to. But this year, I really wanted to take a moment to acknowledge it because it has been a lot—in the best and craziest ways.
Anyone who owns a business (which, I assume, is most of you listening—otherwise, why would you be here?) knows how important it is to celebrate wins whenever you can. So, I would love it if you sent me a DM with your business birthday so I can celebrate you when the time comes, too!
Now, let’s dive into the first lesson. These aren’t in any particular order—it’s not about importance or the timeline of when I learned them. Just eight key themes that have stood out to me over the years.
1. I Would Prioritize Systems Sooner
If I could do it all over again, one of the first things I would prioritize sooner is systems. I can’t even tell you how long I spent manually answering the same emails over and over again. I would literally go into my sent folder to see how I responded the last time—and since my wedding business ran on Outlook (which has the worst search function ever), it was a nightmare. I honestly can’t believe I operated like that for so long.
If you’re still doing that, let me tell you—you need a CRM, like HoneyBook or Dubsado. I’m a Dubsado person now, and I can’t recommend it enough. You also need a project management tool. Before I had one, I would manually track every single wedding and client task. And when I transitioned into this business, I still didn’t prioritize systems for way too long.
When I first started, I was just winging it. It was the middle of COVID, and I figured, Well, I do this for myself—why not for other people, too? And sometimes, you do have to just dive in. But looking back, I wish I had set up systems from the start.
I actually talked about this in Episode 39 of the podcast when I interviewed Colie about her five-minute booking process. I remember realizing during that conversation that I didn’t even have my Dubsado automated to handle proposals, contracts, and invoices in one streamlined process. So between the time I interviewed her and the episode aired, I made it a goal to finally set that up—and it was a game changer.
Beyond using a CRM and email templates, another major step was creating SOPs (Standard Operating Procedures). I did this at the end of the year, and let me tell you—it was not fun. I wish I had done it sooner, bit by bit, rather than backtracking and trying to document everything all at once.
If you don’t have a team yet and everything is just floating around in your head, trust me—take the extra time to document things now. It will save your sanity and create a more consistent experience for your clients.
Looking back at Love at First Travel, I know that while all of our clients had great experiences (just look at the reviews!), things weren’t always consistent. Couples who booked me when I was less busy got more attention than those who booked me during peak times. And while everyone was happy, I know the experience wasn’t as standardized as it should have been. That’s something I’m still working on in this business, but I’ve come a long way.
2. I Would Have Looked At The Data More Often
The second thing I would do differently—and this is a big lesson—is that I would have looked at the data way more often.
I actually talked about this in Episode 1 of the podcast because, as a marketer now, I’m constantly analyzing data. In fact, as I’m recording this on my business birthday (February 2nd), I just had a KPI day yesterday, where I reviewed key performance indicators and entered my numbers. Shoutout to Tayler from Enji for popularizing this idea—it was so fun. And honestly, I think everyone should look at their data at least monthly, if not more often.
One thing I don’t think I’ve talked about much is how, when the pandemic hit, I lost a significant amount of expected income. Even money that was contractually owed to me disappeared when weddings were canceled. I had this moment of Oh my gosh, what am I going to do for cash? So, I sat down and listed out all the possible ways I could make money, along with what it would take to get there.
I don’t remember every detail of that list, but it probably included things like:
- Web design → Would need to learn web design.
- Monetizing my blog → Would need to figure out X, Y, and Z.
- Marketing services → People constantly asked me how I marketed my travel business—how I, as a brand-new travel agent, booked only destination weddings and hit over a million dollars in sales per year. The answer? Great marketing.
So marketing became a natural next step for me. But when I started looking at the data (which, honestly, I hadn’t done much of in my wedding business because I was just so busy), I had a major realization:
💡 All of my clients were coming from my blog and Pinterest—the things I spent the least time on.
Meanwhile, I was pouring days into perfecting Instagram content… which wasn’t bringing in clients. It might have felt good, but it wasn’t driving bookings. That was a huge wake-up call.
So if I could do it again, I would have looked at the data from the very beginning and made strategic decisions based on it. And that’s the second part of this lesson—you can’t just look at the data. You have to actually use it to change your strategy.
For example, Taylor from Enji has an amazing video on how she built her 2025 marketing strategy based on 2024 data. She analyzed her biggest months and asked:
- What were we doing when we had our best months?
- Which campaigns or marketing efforts drove those results?
- How do we do more of what’s actually working?
It’s such a simple yet brilliant concept. And I think it also shows that marketing takes time. You need to be intentional, track your efforts, and then analyze the results before making adjustments.
Let’s say you’re listening to this in mid-February. If you decide that in March, you’re going to go all-in on one marketing message—let’s say you’re a Pinterest and blogging strategist, and your message for the first half of March is:
📢 You can’t hustle on Instagram forever. You’re burning out. You need a long-term content strategy like Pinterest and blogging.
Then, in the second half of March, you shift slightly:
📢 Pinterest and blogging are long-term investments. If you start now, by the end of the year, you’ll have 48 blog posts working for you, compounding traffic over time.
Instead of making Instagram the “villain,” you focus on the benefits of long-term content marketing. Then in April, you can analyze:
- Which message resonated more?
- Which one led to more client inquiries, link clicks, impressions, and engagement?
It’s not just about looking at one Instagram post. It’s about testing, tracking, and refining your messaging based on what actually moves people.
At the end of the day, we all want to take a course and learn the “perfect” way to market our business. But the truth is, the only thing that really works is trying things, tracking the data, and adjusting accordingly.
And trust me, I love a good course—I’ve bought so many. Send me a DM and tell me a course you’re considering, and I bet I’ve already tried it.
3. Outsourcing Needs To Be Intentional
The third key lesson I’ve learned is that outsourcing needs to be intentional—and honestly, this could be an entire episode on its own. Managing finances as a business owner is a huge learning curve, and to be honest, I still feel like I need to learn it better in my personal life too.
Looking back, I spent so much money on courses when, in hindsight, I probably should have invested more in outsourcing. If I could do it again, I would have outsourced sooner but also differently.
Learning to Lead
When I started Love at First Travel, I really wanted a collaborative team—I did not want to be “the boss.” And in retrospect, I think that was a mistake. A pretty big one, actually.
I should have prioritized the sanctity of the brand and taken more of a leadership role from the beginning. I should have had SOPs (Standard Operating Procedures) in place and a clear structure for how things were done under the Love at First Travel brand. Instead, I wanted everything to feel collaborative and equal, and while that sounds nice, it didn’t work out the way I envisioned.
Here’s the reality: people want leadership and structure. They want clear standards. And if they don’t, they sometimes end up taking on leadership roles themselves in ways that aren’t always beneficial to the business. That was a big lesson for me.
With Love at First Travel, the way outsourcing worked was that I hired independent contractors and took a percentage of the booking commission. My role was to provide the brand, the leads, and the business infrastructure (like the website). The agents got to keep the majority of their commission, and I took a cut in exchange for the backend support and marketing.
At the start, though, no one was making anything because commission payments only come after travel is completed. So in 2017, I was booking weddings for 2018 and 2019—which meant I didn’t actually get paid until those weddings happened. That also meant I felt like I couldn’t be too pushy or choosy about how I wanted things done. But looking back, I wish I had taken more ownership.
If I could do it over, I would have been more intentional about leadership. I would have set clear expectations, values, and goals for the team. Because at the end of the day, having a strong vision and shared values is so important when building a business.
Bad Investments & Financial Lessons
This ties into another lesson: I made some bad investments because I didn’t have much money, and I wasn’t always making the most strategic financial decisions.
For example, investing in The Knot and WeddingWire? Personally, I didn’t see a return on investment. I don’t want to be too bold, but I would not do that again. It just wasn’t worth it for me.
And because of the way travel commissions work, I was essentially in “fake it till you make it” mode for those first few years. I had zero money coming in while trusting that everything would eventually pay off. Then, when the pandemic hit, I had been working on weddings since 2018 and 2019—and suddenly, I wasn’t getting paid for any of them. That was rough because I had made spending decisions assuming that money was “guaranteed.” Life is funny that way.
The Pitfalls of Over-Investing in Coaching & Courses
When it comes to outsourcing and investing in your business, I’ve also learned that sometimes we spend money on the wrong things at the wrong time.
I’ve talked about this before, but a lot of business owners (myself included) fall into the trap of investing in coaching when we actually need to invest in team members or service providers. Sometimes we already know what to do—we just don’t have the time or capacity to execute it.
Now, don’t get me wrong—I believe in coaching. In fact, I can credit a lot of my success to amazing coaches I’ve worked with, like Candice Coppola (shoutout to Episode 11!). I wouldn’t have built my wedding business without her guidance. And I love my current coach.
But sometimes, coaching and courses are just shiny objects. We convince ourselves that they’ll be the magic solution to help us reach the next level, when really, we just need to execute what we already know.
Worse, we invest all our money in coaching and then don’t have the funds to actually implement the strategies being taught. This can lead to a scarcity mindset spiral, where we feel financially stressed, overbook ourselves, and end up too busy to even benefit from our investment.
So, my biggest takeaway? Outsourcing should always be intentional.
4. I Would Have Invested in One Main Mentor or Course
If I could do it all over again, another thing I would do differently is invest in one main course or mentor from the start.
I love my tenacity—I’m a roll-up-my-sleeves, figure-it-out kind of person, and I love that about myself. But I think I kept myself stuck in overconsumption mode for too long.
I bought so many $50, $100, $200, $300 courses that, let’s be honest, mostly taught me the same thing. Maybe the first couple of courses were mind-blowing because I was new to business. But after that, I was just chasing the feeling that I was “missing something” instead of actually executing.
Instead of spending thousands of dollars on small courses, I wish I had just put that money toward one high-quality course (like a $1,000 or $2,000 program) that walked me through everything start to finish.
But again, this ties back to financial decision-making. I didn’t have $1,000 to invest in a course, so I justified buying lower-ticket ones instead. And while I learned a lot, it wasn’t the best financial strategy.
I also think there’s this narrative that you can start a business for free, and while technically true, the reality is that starting and growing a business usually costs money. And that’s okay! We just need to be realistic about the investment it takes and properly value our time.
Now, in year eight, I definitely value my time more—and I can see just how much of it I wasted early on.
5. You Should “Try All The Things” When It Comes To Marketing
Number five is something I did back then, and I would absolutely do again: I would try all the things when it comes to marketing.
This is a recurring theme on the podcast, but I truly believe in taking action and experimenting. At this stage in my career, I’m all about prioritizing Pinterest and blogging—people are actively searching for your content, it’s long-lasting, and it’s relatively low effort compared to other platforms. You don’t have to be a professional video editor, and it’s easy to outsource because it doesn’t require showing your face. I could go on and on about why I think Pinterest and blogging are the best, but here’s the thing:
If you’re a new business owner, I don’t want you to just take my word for it—I want you to try things for yourself.
There are people who feel just as passionate about Instagram, TikTok, email marketing, or other platforms—and that’s great! The reality is, you will always get better at the platforms you actually enjoy using.
That’s why, in the beginning, I believe you should experiment. Try different marketing channels, see what works best for you and your business, and then narrow it down to focus on two to three core strategies.
One Quick & One Long-Term Strategy
There’s a lot of talk about diversifying your marketing (and yes, I’m part of that noise). I do believe you need to diversify, but in the very beginning, I think it’s best to start smaller and build from there.
Instead of spreading yourself too thin, start with:
- One quick-working platform → Something like Instagram or TikTok that gets immediate engagement.
- One long-term platform → A strategy like blogging or Pinterest that builds over time and keeps working for you.
Otherwise, you’ll get stuck in the never-ending hamster wheel of social media, constantly churning out content with no long-term payoff.
And let’s not forget—Google prioritizes blogs that have been around for a long time. So while you don’t need to dive into blogging right away, I wouldn’t put it off for too long either.
Experiment First, Then Layer In More
I fully believe in trying all the things at first. See what you enjoy, figure out what works, and then hone in on two to three core marketing channels that are bringing in the best results.
From there, you can start layering in additional strategies. I talked about this in Episode 59, where I shared content ideas. Once you’ve established a couple of platforms, it becomes so much easier to repurpose content and expand your marketing.
For example, I recently worked with a client where we:
- Took old blog posts and updated them.
- Turned those updated blogs into YouTube videos.
So, in summary: Try everything. Find what works. Focus on two to three key platforms. Then, repurpose and expand strategically. That’s the way to grow your marketing without burning out.
6. You Need To Be “OK” Not Having a Life For The First 2-4 Years
Number six—and I wonder if this is going to be a hot take. I hope not.
Before I dive in, I just want to preface this by saying: I understand that everyone’s situation is different. I started my business before having a baby, so I honestly don’t know if I would stand by this if I had been balancing motherhood from the very beginning.
But here’s my take: You need to be okay with not having much of a life for the first two to four years of your business.
I know that sounds extreme. But I think people underestimate what it actually takes to start and grow a successful business.
For those first three to four years, I did not have a life. I made a lot of sacrifices. It was hard. I hustled constantly. And honestly? I didn’t prioritize friendships or relationships as much as I probably should have.
I’m lucky to have a few close friends—some I’ve known since kindergarten and one who started as a “business bestie” but became a real-life friend. But beyond that? I don’t have a huge friend group. And if I’m being completely honest, that’s probably because I went all-in on my business.
The Reality of Prioritizing Business Growth
Before starting my business, I had a corporate job and worked in restaurants. I had a much bigger social circle. But as I shifted my focus, I wasn’t maintaining those relationships in the same way. Instead, I channeled all my energy into building my business—because that’s what I truly think it takes.
Now, I’m not saying you should have no friends or no social life. But if you think you can maintain a super active social life while growing a business from the ground up? It’s going to be really hard. Maybe it’s possible, but I don’t think it’s the norm.
The “Soft Life CEO” Trend vs. The Reality of Starting a Business
Lately, I see a lot of this whole “soft life CEO” or “cozy business growth” messaging online, and honestly? I love that idea. But here’s the thing:
Most of the people who actually get to live that lifestyle?
✅ They already have their business set up.
✅ They already have social proof.
✅ They already have automated systems, email funnels, and a built-in audience that refers them and spreads their message.
They’re not starting from zero.
So if you’re seeing that content and thinking, Oh, I’m just going to start a business and it’ll be easy and flowy and effortless—I don’t think that’s realistic.
Again, I’m not saying it’s impossible. I’m just saying that from what I’ve seen (and lived), it’s rare.
Starting and growing a business takes a lot of work. Obviously, I believe it’s worth it—otherwise, I wouldn’t be here, eight years in, recording this episode. But I also think it’s important to be realistic about what the journey actually looks like.
7. Everybody is Faking It
Okay, the seventh lesson is another hot take—and that is that everybody is faking it.
If there’s one thing I could tell my past self, it’s this: You never know the whole story.
No matter how much someone shares on Instagram or Stories, even if they seem super authentic and transparent, you don’t really know what’s going on behind the scenes.
- You don’t know who’s actually making money and who isn’t.
- You don’t know who still has a full-time job or who quit after 30 days but has a financially supportive partner.
- You don’t know if someone actually works 10 to 2 every day just because they say they do.
Just because people say things doesn’t mean they’re true. And I mean, hopefully, most people aren’t outright lying, though I know some definitely are. But for most people, it’s not about lying—it’s about how we all present ourselves in a way that makes us look good.
Even if someone isn’t intentionally curating their life, we all build a narrative for ourselves, and we naturally share things that confirm that narrative.
The Reality of Online Perception
I always say that I’m a private person, and I really believe that about myself. But I also know that there are people who probably think they know me really well. And in some ways, they do. But in other ways? There are probably things that would surprise them.
Because at the end of the day, we all choose how much of ourselves to share. There are things you don’t advertise on social media, and that’s normal. It’s not lying—it’s just how storytelling works.
And I want to be clear: I’m not talking about the business coaches selling a dream of making $10K in two days. I mean normal people—the competitors you compare yourself to, the high school friend whose business seems to be thriving.
We all assume we know more about other people’s success than we actually do. But we don’t. And honestly? I’m constantly surprised by what I learn.
Two Eye-Opening Moments
1️⃣ A client of mine had a full-time job the entire time I worked with them, and I had no idea. I worked with them for a year before I found out. I wasn’t mad or anything—I was just shocked.
2️⃣ I had a competitor I thought was absolutely crushing it. I used to compare myself to them all the time, thinking, Wow, they’re amazing. Then, I saw them post in a Facebook group saying, Has anyone else had a really slow month? I’m having my worst month in business ever.
I was floored. Their marketing never reflected that struggle at all.
These moments were a reminder that you truly never know what’s going on behind the scenes. And that’s why comparison is a waste of energy.
I don’t care if someone has a full-time job or is having a slow month—everyone has different business and life priorities. But it’s important to remember that the assumptions you make about people may not be true.
We create stories in our heads based on what we see, and when something doesn’t fit that narrative, our brains just tune it out. We literally filter out information that contradicts our perception of someone.
Fun fact: I have a psychology degree from the University of Alberta, and if there’s one thing I learned, it’s this—you can’t trust your brain.
8. Relationships Are Everything
Last but not least, if I had to sum up my biggest takeaway from the last eight years, it is this: relationships are everything.
I have been really focused on prioritizing relationships this year, but I will be honest—it is not always easy for me. I am an introvert, and putting myself out there can be difficult.
I actually talked about this in Episode 3, where I shared how I market my business as an introvert. I still believe that about myself, but I also think I have let that belief shape my actions.
Because I have not needed to put myself out there, I have not practiced it as much. Over time, I feel like my capacity for building relationships has weakened.
When I first started my business, I was willing to do whatever it took—endless Zoom calls, networking, and any opportunity to connect. Now, I avoid calls as much as possible.
But the downside is that I have let my relationship-building skills weaken. That is why I am making it a priority this year, because relationships drive everything in business.
How Relationships Directly Impact Business Growth
I often talk about how Pinterest and blogging are my biggest lead generators for Love at First Travel, and that is true.
However, in this business, referrals are the number one source of leads by a significant margin.
Here is a real-life example:
- A client booked me for blogging.
- That client referred someone.
- That person referred another person.
- That person referred another person.
- And that person referred another person.
One client turned into five new clients, all from referrals (starting with just one business).
Then, that original client recommended me to their mastermind group, which led to even more business.
Relationships are not just about business or money, but when you focus on genuinely building connections, your business benefits far more than it would from any single marketing tactic.
Relationships do not require a financial investment, but they do require a time investment. That is something I truly believe is worth prioritizing.
Final Thoughts: Eight Business Lessons in Eight Years in Business
So that is all I have for you. Those are my eight core lessons, themes, or whatever you want to call them, because they are not all necessarily lessons—just things I have been thinking about and reflecting on over the last eight years, which still feels so surreal.
I can’t even believe it. I am not going to do a long, sentimental outro, even though I would love to, but I just want to say thank you for being here. Whether you have been following along for eight days, eight years, or anywhere in between, I truly appreciate it.
This journey has been a mix of highs and lows, just like any business owner’s path. But I am so excited to see what the next eight years bring. It is wild to look back at how different my business looks now compared to eight years ago, or even just five years ago.
To be honest, I feel like this is the first year I have truly started to feel like I know what I am doing. If you are not at year eight yet and still feel like you are figuring things out, I would say that for me, it was probably around year seven—maybe halfway through last year—when I finally started feeling like I had clarity. I knew where I needed to go, what I needed to focus on, and what was just a distraction.
That realization is still relatively new for me. And of course, my business had a pivot, so maybe you will reach this point sooner than I did.
That is all for me. I will talk to you next week. Thank you, truly.
LINKS MENTIONED
- Watch Enji’s Video on Making Decisions Based on Data
- Hire us to write SEO-driven blog posts for you
- Learn more about our Pinterest management services
- Join Blogging for Bingeable Brands (Use Code PODCAST10 for 10% Off!)
- Learn more about working with our marketing agency here
- Follow me on Instagram
