93: 5 Lessons I’ve Learned in 5 Years of Being a Full-Time Business Owner by Dolly DeLong

93: 5 Lessons I've Learned I've Learned in 5 Years of Being a Full-Time Business Owner

According to the U.S. Bureau of Labor Statistics, nearly half of all businesses fail in the first five years. That’s why I’m incredibly proud to be celebrating my fifth year in business in August 2023! To ring in this milestone anniversary, I’m looking back on my past five years in business and sharing five important lessons I’ve learned along the way. Thank you so much for your support and for being a part of my five-year business journey! Cheers to the next five years!

The Systems and Workflow Magic Podcast is brought to you by Dolly DeLong Education. This podcast is for creative business owners who want to learn tangible steps to automate their business through workflows, systems, tools, and strategies to go from scattered to streamlined with purpose because even muggles can become automated wizards.

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93: 5 Lessons I've Learned I've Learned in 5 Years of Being a Full-Time Business Owner


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Dolly DeLong: Hey, and welcome back to the Systems and Workflow Magic podcast. I am your Systems and Workflow BFF and guide, Dolly DeLong, and I am just so thrilled and honored that you are joining in today. You all, as I am recording this episode 93, I am gushing because this episode is a big one for me. Yes, I know it’s not Episode 100, but it is big in that this month, as in when this episode airs, is the month of August 2023, and that officially marks five years of me being a full-time business owner.

Now that is a huge deal to me. It’s a huge deal. I’m about to share a stat because according to the I’m reading this, okay, so this might sound weird, according to the U. S. Bureau of Labor Statistics, BLS data shows that approximately 20% of new businesses fail during the first two years of being open. And then 45% to 50% during the first five years, and then 65% during the first 10 years.

So only 25% of new businesses make it to 15 years or more. So currently, I have made it past the first 5 years. And because numbers don’t lie for my data, I know I have been slowly and steadily growing year after year and I am pumped. So yes, making it to year 5 is a big deal for me. And so I thought it would be fun to reflect back on the top 5 things I’ve learned from running my own business.

And some of these points are pretty humbling to me, and it still hurts my gut a little bit when I bring them up, but I know that transparency and honesty are really important to me. And I know that these moments, these past moments were stepping stones of learning for me. So that’s why I’m going to share all of this with you.

So let’s kick things off. So the first thing that comes to mind that has really shaped and transformed my business is this, knowing the numbers. So it may sound pretty oversimplified and straightforward, but oh boy, did I ever complicate this in the beginning years of my business? As a matter of fact, this is really embarrassing.

It wasn’t until 2021 that I actually started to look at the numbers of my business because my husband started asking me the question “Dolly, why aren’t you paying yourself?”

Or, Dolly, you are gone for all of these shoots, but there is no, no money coming in. I was really embarrassed. And that was also, it was not only embarrassing, but it was very humbling and it was eye-opening.

And it was a lot of hard conversations. The steps I took to get to know my numbers have been complicated due to my having a very rocky relationship with money. And to be quite honest, this year I feel like I finally took hold of another puzzle piece of understanding the money behind my business.

Let’s backtrack a little. I want to share some points of why it’s important to understand the numbers behind your business. Like what I’ve gleaned in the past five years. So for starters, it’s important to develop a system. So you all know I love systems and workflows, but it’s really important to develop a system of knowing the numbers behind your business because you need to have real data to back up the decisions you make based on the real numbers and not make decisions blindly and based on your feelings. Alright? Also, I’m going to share some systems that have really helped me tremendously Again, the numbers behind my business have been actually hiring out a CPA to help me out during tax season. That’s, that was actually my first hire within my business back in 2018.

And it wasn’t originally Jackie, it was somebody else, but I found Jackie later on and I’m so glad I hired her. And she’s been on my podcast and Hiring Jackie has been the best hire ever. She’s helped me understand the numbers, especially during tax season, because both my husband and I, work for a company and I work for myself. And so I overcomplicated everything, and so I just wanted to Uncomplicate, but I knew I needed guidance.

And so it was really helpful having her on our team and walking us through everything. And she’s helped me out in the past. I don’t know. I’m probably gonna, I’m going to say two or three years. All right I’m going to definitely say for the past two years, she has helped me out tremendously. And it’s getting better and easier for me to understand everything she’s communicating with me because it’s been repetition. 

Another financially fit decision I’ve made this year, as in 2023, was to hire out a bookkeeper. And Anna Marie Knapp, if you’re listening, hi. It has been so helpful having her really take a look at the back end of my business with QuickBooks. And she also works alongside Jackie to help me streamline the numbers behind my business.

And she gives me very informed reports and data to go off of. I say she always helps me on the straight and narrow of my money. That has been a wonderful financial decision. Yes, hiring a CPA and hiring a bookkeeper, yes, it does cost money. But, it has helped me develop a better system and a relationship with money.

And, I am so glad. And, I do want to say, in a couple of episodes, this fall, I’m not gonna, I don’t know specifically the episode number, so please forgive me, and there will be an episode about the difference between a CPA and a bookkeeper. I will have a systems and workflow magic episode all about that, because I know developing, again, a system for your numbers is really important.

Okay, so another financially wise decision I’ve made in the past two years was to hire a Profit First coach, and that is Kelly. And I will have every person, every resource in the show notes, so that way, If you’re the listener, you’re listening later on in the year or next year, whenever, then I want you to reach out to these specific people that I’m mentioning. Okay? Cause they’re amazing. 

Kelly was also on the podcast, and she helped me develop a system for figuring out how to pay myself and how to actually profit. Because Profit First is huge. So again, those three links, hiring a CPA for tax season, hiring a bookkeeper year-round to help me understand the numbers of my business, and also working with a Profit First coach have helped been pivotal for me to move the needle of my business.

Again, this has been a very long process, mostly because of my having a rocky relationship with money, and being scared of money. And learn from my mistake, really allow somebody to help guide you, somebody that you trust and who can break it down for you. And I’ll be sharing this at another point, but because of my type of personality, I like to figure things out on my own a lot.

Or I feel really dumb when I ask questions, and I want to come across as if I know everything, you all. I’m not God. And I’m sure God’s laughing at me because he’s like “Dolly, you can’t know everything. That’s my job.”

But, I struggled. This is one of the reasons why I struggled with asking for help because I wanted to do everything.

That ties into like just knowing the numbers behind my business. I didn’t know how to develop a system so I needed help with that. Those are the three components in point one that really helped me develop a system. 

Now, a second thing that comes to mind that has been really like business changing is this, learning that I should not do business alone.

Now, I don’t mean that I should let other people in my business with me. That is not what I’m saying. So what I’m saying is that I should not isolate myself as a solo business center and keep to myself all the time. Now, this may come as a surprise to many listeners, but I’m actually quite introverted. I know I can be shy.

I can get pretty tired easily and really drained easily. And I can also be comfortable just sitting in my house and working with no one around me. And so I know that doing business alone is not sustainable. Now keep in mind I’ve had some rough patches in branching out to participate in women’s networking events.

I actually This is so sad. I can’t believe I’m laughing about this, but this is how I cope with things, and people. I laugh when I get uncomfortable and upset. I just start laughing. It’s really scary. I actually was very scarred by one specific event involving another photographer who, I just, I still cannot believe happened to me.

This happened in the past, so it’s not like it happened recently, but this is what kept me from really networking myself. I went to a women’s networking event, there was another photographer there, I thought, it was okay for me, as another photographer, to be there. And yes, it’s okay. There can be more than one photographer in an area.

That’s totally fine. This photographer decided to whisper in my ear at the event that the people at that event were her clients and I better keep away from them. And, needless to say, I high-tailed it out of that vent because I heard, I was hearing the message, forward facing, women empowering women. I was hearing that, everywhere.

But then, to have that message whispered in my ear made me incredibly insecure, and I felt like I was going crazy. So I never returned, and I ended up going home and sobbing to my husband. And my husband Ty was like, What is this? Middle school? Dolly, you don’t. Don’t even go back there. This is not worth it.

You’re awesome. He was like, trying to do the nice husband encouragement. And he is always on my team, and he just thought it was ridiculous. And meanwhile, I, of course, felt guilt I don’t know why I felt guilty. It’s not like I was going in there full-on like everybody is my client.

I didn’t even say that I just wanted to meet people and that was a horrible experience. So that kept me away from women’s networking events. So it took me a long time to build the courage to branch out again and to actually want to network and to actually want to get to know other business owners.

Because of that one instance in 2019, I literally thought all women business owners were going to be cruel and kind and total hypocrites. And I wanted to figure, that’s why I wanted to do business on my own and figure everything out in my business and not branch out anymore. Thankfully, my attitude changed with some bravery when I decided to branch out and start pitching myself to online business owners when I got into education.

So I pivoted a little in 2020 to include systems and workflow education. So I started out as a family and branding photographer. I still am, but then I took on a third hat and I decided I’m going to teach other creatives about systems and workflow education. But that took me having to reach out to other business owners because you know why?

You may have heard about this bundle called the Systems and Workflow Magic Bundle. Yeah, I know I’m being funny, but I talk about it all the time, so I know if you were an OG listener, you’ve heard about it. But, that was an idea I had back in 2021 that came to me because I wanted to collaborate with other business owners to create a resource that would help creatives with the systems and workflows on the back end of their businesses.

But I knew I couldn’t do this alone. So I literally did the bravest thing I could think of and I started reaching out and developing online relationships. And guess what? Not all business owners are horrible. A lot of them are genuine, kind, and compassionate. Because you’re human. And some of my best relationships now are from the pitches I made several years ago.

So the lesson I learned from that is never do business alone and stop assuming that everyone will treat you like dirt based on one bad interaction. Keep on pushing through any insecurities you may have or just push through any insecurities that people push on you, okay? And continue to develop relationships both in person and online.

And I am preaching to the choir because I always have to remind myself when those bubbling feelings in my gut just start coming up. It’s going to be just like 2019 when this person says one thing and means another thing like not all people are like that all right.

 So lesson three has been a big one for me keeping my health needs to be my main priority and it is something I have struggled in the past five years committing to. Like making sure my body is well taken care of.

It’s sad because I grew up super healthy, y’all. I played basketball. I was an athlete. I ran cross country. And when I got older, I used to run half marathons and would even run for fun. And my favorite workouts were high-intensity workouts. Like I loved working out. Yeah, when I got pregnant with Blaze, that all went down the drain. Like in 2018 that literally all went down the drain.

Coupled with the fact that I was thrown into my business full-time. So if you haven’t heard my story yet, you should know. A quick answer to this is I was forced to start my business full-time. in 2018. I wanted to continue my job where I was working, but that did not work out.

So in 2018, I grew two babies. Okay, my business baby and Blaze. Which is the better baby because he’s human and he’s my son. So I had my head down in my business to try to make it successful. So because I had my head down so much to just work on my business, I neglected my health and wellness.

And that has been one of my biggest regrets for the past five years. And so now that I’ve had Jack, my brain is pretty clear from the newborn stage. And I’m actually taking, no pun intended, baby steps in incorporating health and wellness back into my life. And I know that it directly impacts the way I run my business now.

One of my goals is to run another half marathon by the time I turn 40, which, spoiler alert, is next year. And I want to be able to run and still have so much joy from running again, the way I did in my 20s. I want to run for fun, and I just… I just want to enjoy it again. I want to get that runner’s high again.

I miss that feeling and incorporating working out again has been incredibly hard for me while growing my business because I work in the crevices of motherhood and I honestly feel like every waking moment is dedicated to making my business grow in the past five years I know I have grown so much business-wise. I have made so many strides, but your comparison is a thief of joy, and I always feel like I am so far behind everyone else. So I have felt guilty for working out when I knew I could have been working on a funnel working on an email sequence or working on my inbox. And it all added up in the past five years and I knew it had added up because during my last pregnancy with Jack, I had a lot of health issues and I knew a lot of them stemmed from not leading a healthy lifestyle.

A lot of them were preventable on my end and I knew something had to change. So I gave myself a timeline in my head and I said, as soon as Jack is weaned off of me, I’m going to get back into consistent working out because, for me, I wanted to make sure I didn’t have to pump around the clock. And I also wanted more flexibility.

So around May or June of this year, specifically May, is when I started slowly incorporating walking back into my life. So it’s now July when I’m recording this, and instead of waking up every day at 4:30 to work, which I used to do, I now wake up at around 5 a.m. three days a week, and after feeding Jack, I go for a one-hour walk by myself.

And it’s very refreshing. It’s been so helpful for me. And it’s going to be a while before I can run a half marathon again, but I am taking baby steps. And you all as of this recording today I ran half a mile. I didn’t know it was half a mile. I actually asked my husband I told my husband hey I ran from the bank at the corner to our house and he confirmed it was a half mile and I was very proud of myself. So I am starting my running journey very slowly. Okay.

So I am, I’m really happy. I’m slowly coming back to myself. And so a huge lesson for me is even though I’m building a business, I can still take time for my health because my biggest why is my family. I want to have a successful business for my family, but if I’m constantly worried about my business and I’m not taking care of my health, then I’m not focusing on my why.

It’s like all these circular things. I’m about to get a little, I’m warning you, I’m going to share a Bible verse, okay? Mark 8:36, says, “What good is it for someone to gain the whole world yet forfeit their soul, forfeit their life?” And I’m sharing this because what good would it be if I just worked and worked and worked and lost out on the things that mattered the most?

And for me, that’s my health, that’s my family. And I, that is a huge reminder. That verse is a reminder to me. So I wanted to share that and I will always be happy to share my favorite Bible verses too. Okay, let’s go into the fourth lesson I’ve learned in the past five years since this. I am so happy that I’ve heavily leaned into content marketing.

And here’s what I mean by that. All right, there is so much power in long-form content marketing. Okay, so when I say long form, I’m talking about either blogging or audio format, such as a podcast or video format, such as YouTube, for example. And so many business owners actually don’t take advantage of these forms.

These long-form content marketing, like I call them hero pieces, because one, it may take up too much time to develop a system for content creation. And two, there’s just so much noise in this online space that you don’t know who to listen to and even where to begin. And I get that, but let me share some benefits I’ve experienced from long-form content marketing, specifically through my blog and through my podcast, okay?

One, I have great SEO, and that stands for search engine optimization. I am actually searchable for several key terms that I want to be known for, and I’ve had clients who have found me on Google and who continue to find me on Google, not just social media. Okay. And that’s huge. And two, because I have leaned heavily into content marketing, I can showcase my expertise on platforms I own and again, not depend on social media. 

I love social media. If you follow me on Instagram, you know this. I love it, but it’s very fickle and it’s draining. And it’s changing all the time, and you don’t own it. Okay? So in the past five years alone, I have seen the rise and fall of different social media platforms.

What has stayed consistent? Blogging, and also in the past years since I started it, podcasting. So for me, leaning heavily into long-form content marketing. I started these different types of content marketing through blogging first. Because I am a photographer that was the easiest way to get my content displayed for the world to see and to showcase my work.

I also took some great courses on SEO and blogging and how it applies to my service-based business. And I will be forever grateful for those investments. Those were really good investments. I also invested in a podcasting VIP day with Haley Gaffin in 2021. When I decided to take on another long hero content piece, long-form content marketing, which was, which is now, you’re listening to it, podcasting.

Now I made sure that I felt confident in blogging before I took on two main forms of hero content pieces. Just to be totally transparent. I am not saying that you should do all the things right out of the gate because I literally waited two years to start this podcast. I originally wanted to start it in 2019, but I actually purposely waited until the fall of 2021 when I had a system down pat for blogging under my belt.

So my encouragement to you, the listener is this, take baby steps develop a system for yourself, and make sure you are Incorporating some sort of long-form content marketing into your business. Because you don’t own social media you should be creating content that’s evergreen, that lives on platforms you own. And also so that you can build out authority in your field. Alright? 

Okay, let me share the fifth lesson I’ve learned in the past five years of owning a business.

The lesson is this, are you ready? I don’t have to know everything to be successful. This has been a hard pill and lesson to swallow, because I am the queen of wanting everything to be perfect, and I also want to know everything about a particular topic before I even think about educating others. But here’s the thing, Systems and workflows are constantly ebbing and flowing and changing.

Also, it’s a sign of a really good teacher if they’re also willing to be a lifelong learner. I believe that. I also believe that I’m not going to figure everything out. I can’t. I’m not like I shared this earlier, I am not God. I can’t know everything. That’s impossible. I’m not a robot. But I struggle with this because I want to be trusted and I want to be seen as everyone’s systems and workflow BFF.

And I want I know I said the word trusted, but I want to be a trusted voice, a reliable voice in this overcrowded online space. And since I struggle with this concept of perfection, it really drained me to the core. Because every time in the past when someone would hire me for a specific job, I always had this nagging feeling that I was going to mess up because I don’t know every facet of that type of service.

For example, I would get I was absolutely sick to my stomach when I would offer Dubsado setup services because even though I had been Dubsado certified, and I knew Dubsado, it was also changing every few months and it made me sick to my stomach because I felt so much pressure to memorize everything.

And that’s impossible. isn’t that so miserable? Like I’m just me talking about this. I’m like, that’s miserable. So I put myself through so much misery for years until this year. I decided to hone in on very specific services within my business. And I decided to take out Dubsado setup days because it was making me sick to my stomach that I only knew, this is laughable, I only knew 95% of the interface, like the app, and not 100%, like some crazy robot. Like I know I’m weird. So when I say I want to over-deliver, I mean it. I want to over-deliver and I want to be a good system and workflow guide.

And I never want to think, come across as this stupid idiot. I know. If you’re like, you’re allowed to laugh at me because like we all we all have to learn and ask questions. And that’s something I struggle with. Now, I do want to say I may reopen my Dubsado services again, but I had to take a step back this year and calm the heck down with my perfection tendencies and actually learn how to enjoy Dubsado and enjoy learning for the fun of it and not pressuring myself all the time. 

It was miserable, you all, and because now that I’ve taken it out of my services I’m having so much fun relearning more about the new facets of Dubsado and it’s making me so happy to have that zeal again within me.

So that has been a big lesson for me these past five years. I can still be an expert, but I can still learn at the same time. 

So I know I went a little longer in this episode, but I just wanted to share so much I have learned and am continuing to learn from owning my own business.

It’s definitely been wild and fun, like an emotional high, emotional low like a roller coaster of a ride, but I’m just I’m so happy I own my business. I’m grateful that God has blessed me with the season of life, and I pray that I can honor Him as I continue to grow in my business, on, my photography side, and in my systems and workflow education side. And I hope I can, I want to glorify Him in the lows, too, in the seasons where I’m like, I don’t know everything.

I’m miserable. I, nothing is going my way and I want to honor Him when I’m, like, shouting from the rooftops or shouting from the mountaintops. I want to honor Him every step of the way. So anyway, thank you so much for listening in. I’m, again, this has been, I know this is a very unique episode, but I just wanted to do something different.

And thank you so much for listening in. And, again, for links and resources and people mentioned in this episode, head on over to the show notes and to the blog associated with this episode. Alright? I’ll talk to you all next week, you amazing Muggle you! I hope you have a wonderful day. Bye! 


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