BTS: My rebrand to Out of Office Entrepreneur

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why i rebranded my business

OMG, another rebrand?!

If you’ve been here for a while, you know that I just rebranded from my name (Erin Flynn) to Successfully Simple two years ago.

So you might be wondering WHY another change in name? What the heck is going on? Let’s dive into the why and how of my rebrand to Out of Office Entrepreneur!

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Successfully Simple isn’t working out with my audience

While I like the name, Successfully Simple, it’s been a little too broad and vague. What does it mean? Who is it for? It’s not clear.

While clarity could of course come from the brand itself, messaging, etc. Successfully Simple just didn’t seem to be clicking with my audience.

In fact, everyone was constantly messing it up. Simply Successful? Success Made Simple? Or some other variation.

While the name isn’t everything, it isn’t a good thing when it’s confusing.

Successfully Simple is blocked!

For 8-10 months I’ve been trying to get Successfully Simple un-blocked on social media.

What would happen is that as soon as I would add a domain email (meaning to a social media account, the account would be shut down. This happens on Instagram, Facebook, and Twitter.

I have spent months, and lots of money, trying to get this fixed. But no one can tell me WHY the domain is being blocked (and trying to get an answer out of a social media platform is impossible). It’s not blacklisted or anything, but when using the Successfully Simple domain on social, I get a message that I’ve violated the platform’s terms.

Which BTW, I personally haven’t done anything that could have gotten me blocked as I was blocked the first time I tried to use the domain email on these platforms, and have other accounts with absolutely no violations using other email addresses.

So whoever had the domain before me must have been a spammy jerk.

With this domain issue, I didn’t feel like it was worth trying to get the Successfully Simple brand to click with my audience.

So after a lot of consideration, wasted money, and wasted time, I decided I needed to move on from the Successfully Simple name as a brand (I am still going to use it for one of my programs, since it is a good fit there!).

Why Out of Office Entrepreneur?

Knowing I wanted to move away from Successfully Simple as my brand name, I started brainstorming other names I could use.

The problem? All the really good ones where taken.

Then, one day, as I was driving home from the grocery store, “Out of Office Entrepreneur” popped into my head.

And I loved it.

It perfectly describes what I do and teach!

It’s much more specific about what it is and who it’s for, and when I ran the idea by multiple entrepreneur friends, it was an immediate, “Oooh, I love that!” with everyone.

To be fair, the domain is a little long, and I hate the double ee in it, but overall, the name is spot-on. Besides, who actually types in domain names? 90% of the time people will be visiting by clicking a link, so an ugly domain isn’t the end of the world,

(I also got oooentrepreneur,com, but since I am trademarking the name, I decided to go with the whole thing spelled out.)

The Rebrand

I was already heading this way with Successfully Simple, but now with the new name of Out of Office Entrepreneur I feel like the messaging and branding is much clearer.

I help creative entrepreneurs spend more time out of office without hiring a team.

Boom. Clear and concise.

While I didn’t need to rebrand for this messaging, something about the new name just made everything fall into place.

And then, I decided I wanted to launch the rebrand for the 10th anniversary of my business. Because, of course. It just seemed so perfect.

It was mid-November, and my anniversary is January 1, so that gave me about six weeks to make it happen.

Brand and website design

If I’d had more time, I probably would have hired out my brand design. While it’s something I can kinda do and understand  (as a web designer) it’s not my strongest talent.

But with a six-week timeline for the entire rebrand, and holidays during this time, I knew I’d need to tackle the job myself.

I wanted to keep the minimalist style of Successfully Simple, but add in a little more personality and get the vacation vibes flowing. You’ll see more palm fronds and beachy touches, since that’s what most people think of when they think vacation!


Although I’d just had a brand photoshoot with Amy Riordan at the beginning of November, since I didn’t know at that time that I was going forward with the rebrand, (although I love the photos) the vibe isn’t quite right in most of them, and the theme/shots is more work-y and less vacation-y.

A collage of photos of Erin Flynn

And despite the fact I’ve personally gone on some really cool vacations while running my business (places like the Amazon rainforest, Galapagos islands, safaris in Zimbabwe, Zambia, South Africa, etc.), I don’t travel with a professional photographer, so most of my photos from these trips are not website-worthy.

So I tapped into some stock photos from Haute Stock and Pixistock, mixed them in with photos from my shoot, and it’ll do for now!

Tools used

The brand and website came together in about six (half) days spread over two weeks. I designed both the brand and website in-browser using Beaver Builder and Canva.

I know, past snotty-designer-me would have been appalled!

But time was a big factor, and I still had a ton of copy to write and tech things to change.

When you only work 10 hours a week, you don’t get caught up in finding the “perfect” shade of green that you’ll still change five times. You take action and get things done. Improvement can come later.

Tech changes

Changing domains is always a PITA. And a lot of things can’t be changed until after the new brand is launched, or my audience and customers will be too confused.

I’m talking things like:

  • The name of my Teachable school (which also shows up on recurring billing payments)
  • The email I send newsletters from
  • The URL you go to to login to your accounts or read my blog
  • My social media handles

If you know me, I don’t like to wait to do things. The faster I can get something off my to-do list, the happier I am. So waiting to make these changes is something that I find very annoying, but by the time you are reading this, everything should hopefully be done!

The future of Out of Office Entrepreneur

So what’s next? Well, a lot! I’m growing OOOE beyond just me, so the future will include guest bloggers on a variety of topics and lots more content for you!

The two biggest changes right now are…

Retirement from web design

I am officially retiring from web design to focus on OOOE. It’s something I’ve been wanting to do for several years now, but always kept my toe in because… well, it’s hard to quit when people want to hand you thousands of dollars.

But, honestly, I’m just not that into web design anymore. I’ve been doing web design professionally for 10 years now, and making websites for another 13 years before that, and… I’m bored.

It’s been a struggle for me to want to stay on top of all the new cool things in the world of web design when I’ve been feeling this way, and now that I’ve expanded my courses beyond just ones for web designers, I don’t feel obligated to always be up to date.

I’m much more excited about implementing and teaching systems to help myself and others spend more time out of office, so I’m excited to finally be going all-in with teaching!


I rebranded from Successfully Simple to Out of Office Entrepreneur which is a much better fit for my business!

I’ll be putting a lot of effort into my courses so if you want to save time in your business and spend more time out of office, join us!