Hi! We're Jason and Caroline, a husband and wife creative team taking you behind-the-scenes of building our new business from scratch. Poke around and watch us figure it out as we go!

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Day 107, An Update On All The Thangs!

Day 107, An Update On All The Thangs!


We wrote this post to give you a general update of where things stand with Wandering Aimfully, along with a few lessons we’ve learned thus far. Ready to dive in? Let’s do it!

During the first few weeks (waaayyy back in March) we had a tidal wave of momentum building Wandering Aimfully, but things have slowed down quite a bit. Maybe you’re feeling it too? Fear not though, we’re still cranking along behind the scenes! When time gets short and there's work to be done, some things just have to give, and for us that usually means posts on this under construction site. But we hope this update post will give you an idea of everything we've been up to on the days we haven't been posting.



This project started publicly in late March with a very aggressive goal of launching on May 1. That didn’t happen. We pushed the launch date back to late June, but as that date approached, it became clear it just wasn't going to happen either. Womp womp.

These delays were partially due to unrealistic expectations of ourselves, but mostly due to unforeseen challenges with building our customer dashboard and website. When faced with the choice between sacrificing quality/our vision or pushing our launch back, we chose to push the timeline.

If you’ve followed our work at all over the years you know that deadlines are important to us, so it’s been particularly rough to have our launch date be a bit of a moving target. But...

Wandering Aimfully WILL launch on August 22.

No ifs, ands, or buts. Whatever it takes, we have to get our new site up otherwise we might have a mental breakdown and throw our laptops out our windows 😂. 

Lesson learned: We believe in constraints and see them as valuable parts of the creation process. However, if things are out of your control, be flexible enough to move your own arbitrary deadlines. 



There is no sugarcoating it, working with developers has been the toughest part of building Wandering Aimfully. Now, let us be clear, we’re working with really talented people, it’s just that working with anyone outside of yourself will inevitably bring some bumps and bruises. Communicating your vision and expectations—especially for a project with this kind of scope—is bound to be difficult.

Even as recently as two weeks ago, we had to switch up our front-end developer and that has brought about a bunch of unique challenges we were hoping to not to have to deal with. The past few weeks have been focused on moving the Wandering Aimfully project to a whole new set of proverbial train tracks and writing a bunch of documentation for a new front-end developer to help bring our website designs to life.

To get real with you guys: This part of the process has not been fun. At all. 

But, it is what is and we realize we have no choice but to move forward and come up with solutions if we want this vision to come to life. We have to do what it takes to get Wandering Aimfully built and out into the world, so we'll dodge whatever curveballs get hurled our way. 

Lesson learned: Do your best to understand the work capacity of the freelancers you choose, but even the best ones may have life issues come up, so always be prepared with a plan B (from the start!).



We recorded an unedited meeting where we checked in our on content migration (we'll share that video next week). Caroline and I have easily spent 100+ hours updating our previous 407 articles and optimizing them for the new Wandering Aimfully article layouts. 

The articles flagged with a status of "Not Started" are the scary big ones 

The articles flagged with a status of "Not Started" are the scary big ones 

In the meeting, we talk about changing up our content migration strategy, especially as it relates to our larger in-depth guides (which combine 5-20 articles into 1 bigger article). We have 5 in-depth guides left to create and approximately 60 articles to clean up and format. 

Lesson learned: Content migrations are tedious and simply take a ton of hours if you want to do them right. Know this and keep reminding yourself you’re investing in the future of your content, and, ultimately, your business. 



You may already know the sales strategy we’re going to use, but we thought we’d remind you just in case. Once a month we’ll be opening up the doors to add 30 new Wandering Aimfully (WAIM) members. Memberships will cost $100 per month or $1000 per year. Here are the exact steps we’ll be using to sell memberships:

  • Flip a switch on the backend of our site to turn sales “ON” (this is important because it actually swaps out certain sections of content on various pages to let visitors know the membership window is open)
  • Email subscribers that have joined our list since the last sales window ended will get the full sales email sequence outlined here:
    • On a Monday, send an email to our list announcing memberships are open
    • On the next day, Tuesday, send a sales email explaining more about WAIM
    • On Wednesday, send another sales email
    • On Friday, send another sales email
    • On Monday, send the final sales email
  • Email subscribers that have already been through our sales window once will just get the Monday announcement email in our newsletter and a reminder the following Monday when the membership closes

(Those steps are very simplified, but there's a bit more complexity behind the scenes which we'll share in the coming weeks. Also, our "sales emails" will not be boring standard sales emails.)

One thing that will be interesting to watch, especially during our first sales window in August, is if the 30 membership spots fill up quickly. If we get 30 new members in the first couple days, we don’t have to continue to send additional sales emails and can simply go back to our helpful weekly email content. We also have a goal of 300 total paying members inside Wandering Aimfully. This is what we call our "enough number" (so we don't have to keep chasing more and more money and members) and we're going to share the journey to reach that goal publicly on the new WAIM website. 

As a reminder, we’re only selling 30 membership spots each month because we want to give a hands-on experience to our new members. We also think this is the best way to avoid having the existing community get inundated with too many new faces.

Oh, and we still need to write our sales emails and the copy for the sales page. 😬😝😬

Lesson learned: No lesson to be learned here yet, but sooo many lessons to be learned once we start using this sales strategy and see how it goes!



For years we’ve used a pretty simple strategy when it comes to onboarding new email subscribers. We email them! Haha. Truthfully, with exception to email lists dedicated to our online courses (Caroline’s Better Branding Course or my How To Get Sponsorships course), we didn’t ever do much with email onboarding. That’s going to change with Wandering Aimfully. 

We want our email list to be full of passionate and action-taking people. We aren’t interested in having a large email list of passive readers. I’ve personally been down that road, and having more passive subscribers does not equal a healthy email list. Instead, we’re going to put ALL new subscribers into a 5-day series of emails where we share our Working To Live framework and try to immediately help people make a change in their lives. Sure, this 5-day email sequence can be skipped, but we really want to try to weed out passive subscribers and have a list of folks who want to make change in their lives and are willing to do the work. 

Lesson learned: The main lesson here is that I’m very grateful to have Caroline’s email workflow automation skills at our disposal! She’s doing some pretty tricky stuff with Drip (our email provider) and we’ll learn a bunch once we have things setup and new subscribers going through our onboarding automation



If you didn’t get a chance to watch the unedited meeting where we fully explained (and did a trial run of) Wandering Aimfully The Show, we recommend giving it a watch: 

The show will be the two of us sitting at opposing mics, exploring topics that we find interesting and possibly share differing viewpoints on. We’ll record video of the show and share it weekly on YouTube and through all the podcasting apps. We see the show as an opportunity to share our ideas, while also trying to be helpful and entertaining (it is a “show” after all). 

Our goal is to get 8-10 show episodes recorded and ready to share starting in September. There’s a crap-load of video editing in my future! 

Lesson learned: Our kitchen counter is not a comfortable recording environment, so we purchased a foldable $35 round table to record from. Fancy! 😆



We aren’t creative entrepreneur robots and we do have lives outside our laptops (I think??). 

Vacay: As of posting this update, we’re heading on a 5-day vacation with friends. We thought WAIM would be launched before this trip (so it was supposed to be a bit of a celebration), but alas it wasn’t, so, yay for another trip amidst building our future biz! Can’t complain though, we’re ready for a little break. 

Shopping: Caroline and I have recently come up with a bi-annual shopping plan. Essentially we give ourselves permission to buy a few new clothing items twice a year, usually in the Spring and Fall. Because we have a pretty minimalist wardrobe (we own about 100 total items between us, all seasons, including undies, workout gear, etc) we wear through stuff very quickly. We set a budget and go through our closets pulling out items we’re going to donate and replace. We always try to use a 1-in-1-out rule. FWIW, we grabbed most of our stuff from Marine Layer this time around. 

Exercise: We finished up our first-month doing OrangeTheory workouts. I thought I was going to hate it, but quite the contrary! We did 12 workouts in our first month, I burned nearly 11,000 calories, and Caroline burned 7,500 calories. It’s definitely not the cheapest workout, but we are happy to invest in our health, especially when we can find a workout program we genuinely enjoy doing together (and that takes little mental effort to commit to!).

Orangetheory workouts: No joke.

Orangetheory workouts: No joke.

Tesla: Speaking of milestones, we just hit the 2-month mark of owning our Tesla Model 3 and we could not be happier with it! We had to take FILAM3NT (yes, we gave our Tesla a nerdy name) in for a quick service appointment a few weeks ago, but the experience was smooth and quicker than we expected. Otherwise, owning a 100% electric car has been a blast and we cannot recommend the Model 3 enough. We plan on filming a weekly-ish video talking about living with a Tesla, but that will have to wait until we get our WAIM-biz-ducks in a row. 



Alrighty, we hope you enjoyed this update and appreciate you greatly! It really does mean a ton to hear from you via email, Twitter, Instagram, and in the YouTube comments of our videos. We’ll be launching Wandering Aimfully before you know it, and we hope it brings you a ton of value!

Thanks, friend! 

Content Migration Status Update: An Unedited Meeting

Content Migration Status Update: An Unedited Meeting

Our Strategy Session for Wandering Aimfully: The Show (YouTube + Podcast Plans)

Our Strategy Session for Wandering Aimfully: The Show (YouTube + Podcast Plans)