Episode 002. My Business Journey and What I'd Do Differently If I Started from Scratch


They say hindsight's 20/20, so here's a good question for ya...

If you were warped back in time and had to start your business all over again from scratch, knowing what you know now, what would you do differently?

My answer? … Keep reading!

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Welcome to Episode 002 of the Content Boss podcast!

In this episode, I break down:

  • The 5 phases my online business has evolved through over the last 3.5 years, and where I’m at right now (hint: it involves the word “Content Boss-dom”)

  • The truth about what was really going on behind-the-scenes when I was travelling as a digital nomad back in 2017… spoiler alert: it wasn’t pretty

  • Exactly how I’d set up and grow my business if I had to start it all over again from scratch (spoiler alert—I’d do at least 80% of it differently!)

Whether your business is brand new and you want to get ahead of the curve or you’ve been at it for a while but something just isn’t clicking, this list of my 7 "do-overs" should help you get your biz on the fast track to success.

Check out Episode 2 on iTunes by clicking here or listen in below:

The 5 Phases of My Business Evolution

My business has been through a LOT over the last 3.5 years. I’ve been through a lot. Here’s a quick recap of the five different stages I’ve evolved through, from the very early stages of my business to where I’m at now.

Phase 1. Krista the Freelancer

I launched my website and business, which went by the name of “Blog Beautifully” at the time, on April 1, 2016. So nearly 3.5 years ago at the time I recorded this episode!

In the first phase of my business, I was offering 1:1 services both as a Blog Coach and a Pinterest Manager for entrepreneurs. True Story: I charged $30 for my first ever 60-minute 1:1 coaching session. I know, I know — what was I thinking!? But hey, live and learn!

By September 2016, my Pinterest services were pretty much booked out and I started looking into other avenues for reaching more people and making more money. This led to Phase 2 of my business evolution…

Phase 2. Krista the Course Creator

In October 2016, I launched a Pinterest course for bloggers called ‘Pageviews from Pinterest’. I had around 25 students enroll in my course, and it was my first glimpse into what might just be possible if I could focus more of my efforts on creating courses instead of 1:1 client work.

Over the next few years, I went on to launch 6 more programs for a total of 8 courses (I’d launched my very first course earlier that year in June 2016 – but more on that in Episode 4!).

Needless to say, I fell head-over-heels in LOVE with online courses as a business model, and they’re still my main source of income to this day.

Phase 3. Krista the Digital Nomad

My business was making pretty good money by the time summer 2017 rolled around, so in June of that year, my boyfriend quit his job, we bought a 24-foot RV, and we set off to travel around Canada and the US while living in the RV and working remotely.

I know, it sounds insane. And also super fun. And truly, it was a bit of both!

While we originally planned to travel for an entire year, we ended up cutting our trip short and coming back after just four months. This was due to a few different things, including:

  • My grandma passing away in September 2017 and me flying home for the funeral

  • A big hurricane in the southeastern United States right as we were about to head that direction with our RV (RV + hurricane = no bueno)

  • Something I haven’t talked about much online before: The summer we were travelling, I began experiencing some pretty debilitating mental health issues. Namely, depression. I went through a 6-month period of major depression for the second time in my life (I’m incredibly happy to say I haven’t experienced it since this second time).

Phase 4. Krista the Multiple Business Owner

In June 2018, I launched my second business, kristadickson.com.

Did you know that I have two businesses? Well, now ya do! ;)

Why did I branch out, you ask? Well, to be honest, I’d started slowly falling out of love with what I was doing and teaching my audience on blogbeautifully.com, and I was craving something new.

Over the course of a few months, kristadickson.com evolved into a business centered around what I’ve dubbed “soulful weight loss” — AKA: losing weight in a soulful, aligned, intuitive way.

I ended up closing down blogbeautifully.com for around six months in 2018 while I focused exclusively on growing kristadickson.com — but in the end, I missed it too much! So I decided to re-open Blog Beautifully in the Spring of 2019.

Running two businesses isn’t always easy, and I’m definitely not perfect at it. But with that said, it’s incredibly rewarding to be able to serve women in two completely different ways and get to share two of my biggest passions with the world.

Phase 5. Krista the Content Boss

And finally, we arrive at the stage I’m currently in: Content Boss-dom (is this a word? I’m 99% sure it’s not, but umm, can we make it one?).


In the summer of 2019, I rebranded my business and changed the name from “Blog Beautifully” to “The Content Boss”. I revamped my website and pivoted my niche juuuust slightly. Instead of talking solely about blogging and social media strategies, I wanted to focus on content marketing and copywriting for digital entrepreneurs — my biggest sweet spots and two of my absolute favorite things in the world to talk about. Like, EVER.

Fun fact: I actually had the idea for this rebrand almost TWO YEARS ago, at the end of 2017. when Scott and I had just come back from travelling.

But guess what? Imposter syndrome crept in, and with it came thoughts of, “I’m not a good enough writer”, “Who would listen to me?”, and “Why would anyone want to learn from me when there are so many other experts who are smarter and better than me?”

Have you been there before? Imposter syndrome is a nasty little bugger and in my opinion, one of the biggest dream killers of all.

So needless to say, although I had the idea almost two years ago, I didn’t pursue it. I went ahead and launched kristadickson.com. Which, looking back, I’m so glad I did — so I suppose it all worked out in the end!

And now that my Content Boss baby is out into the world, I’m 1,000,000% happier in my business than I’ve ever been before. When you land on that one magical thing that you’re just MEANT to do, it feels like nothing else, promise!

How I’d Build MY Business From Scratch

My business journey has been far from perfect, and I still struggle with a lot of things to this day. However, I thought it might be interesting if I shared the 7 big things I would do to build from business from the ground-up if, for some reason, I had to start all over.


1. I would HOST my website on Squarespace.

I was a WordPress girl through and through for YEARS. I mean, my first online course was all about WordPress for crying out loud! So why the change in tune?

After switching both of my websites from WordPress to Squarespace in the last 12 months, I can honestly say it’s a world of difference. Much easier to manage, and for someone like me (ahem, let’s just call it “design-challenged”), I’ve actually found it relatively easy to create a decent-looking website using Squarespace. ‘Nuff said!

2. I would buy design templates for everything.

Again, design-challenged entrepreneur over here. 🙋‍♀️

Instead of struggling like a mofo and ending up with crappy looking PDFs, workbooks, and course slide decks, I would simply head over to Creative Market, browse for some pretty templates, and use those templates to build a professional-looking brand while also on a budget.

3. I would focus on growing my email list.

I actually did this pretty well when I first started my business, so I can give myself a small pat on the back for this one. This was because all of my gurus at the time had drilled it into my head that the money was in the list.

And hey, it did pay off! Nowadays, things have come pretty much full circle and I actually teach a course all about list-building. Crazy, huh?

Pssst. Need some help with your list? Start here with my free in-depth guide: 50 Ways to Grow Your Email List Today.

4. I would focus on Pinterest and Instagram.

Pinterest is incredible for driving traffic to your website and Instagram is amazing for building connections and relationships. Together, they’re one lethal duo! Lethal as in: you’ll be SLAYING the game in no time.

Not following me on IG or Pinterest yet?!

Check out my Pinterest here!

And click the feed below to creep my Insta! (@thecontentboss)

5. I would focus on selling courses and group programs.

Offering 1:1 services is a great way to get started in online business but they just aren’t scalable like courses are. If I were starting all over again, I would do a mixture of both 1:1 services AND courses until I was making enough money to step away from client work and focus solely on my courses.

>> Been thinking about creating a course? I’d love to help you out! Grab my free 3-Phase Course Launch Checklist here.

6. I would learn and implement sales funnels sooner.

Here’s an update, cupcake:

You do NOT have to wait to start using sales funnels in your business.

You might be telling yourself things like, “Well, once I have a five-figure course launch I’ll set up a sales funnel,” or “I need to have a few more programs under my belt before I can create a funnel”, or “Sales funnels are so complicated. I’ll never figure it out!”

Trust me, sales funnels do NOT have to be crazy complicated or take a million years to set up. And you don’t have to wait!

I’ve been focusing a lot on my sales funnels this year (2019), and one of my biggest regrets is that I didn’t put more time into this sooner. It’s a game-changer, trust me!

7. Hire my Creative Assistant sooner.

If you know me, you know I’m aaaall about having a small-but-mighty team and using my WORDS to scale my business, not a dozen staff members. But truly, I can’t IMAGINE running my business without my incredible assistant Amanda. She’s only been helping me for just over three months and I’d already be lost without her.

I know everyone says that they wished they’d started outsourcing earlier in their business, and I hate to be a cliché, but it’s soooo true. I don’t think you need to go crazy and hire a bunch of people right away, but I do suggest figuring out what your biggest weakness is in business (design, tech, finances, marketing, etc.) and hiring someone to help you with at least that one thing.

How would you start your business all over again?

That’ll wrap up this episode of the Content Boss podcast! I’d love to know in a comment below: If you were to start your business all over again from scratch, would you do anything differently? What? What would you focus on in the early days to get up and running quickly?

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