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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What Most Entrepreneurs Don't Want You To Know: This Sh*T Isn’t Easy

What Most Entrepreneurs Don't Want You To Know: This Sh*T Isn’t Easy


When you encounter the tough moments of a project, it’s important to remember that building your dream IS going to be difficult because no one's built exactly what you’re trying to build.

You may have noticed that things haven’t gone perfectly for us these past few weeks. Last week was a particularly rough week because the control of our member dashboard was no longer completely in our hands (because it was being completed by our developers.)

When we were in the thick if it, I decided to jot down some of the difficult things we’ve run up against (yet again, trying to share the truth about what it takes to build something like Wandering Aimfully). My goal in sharing this post isn't to sound all doom and gloom, it's to share the realness of what's going on behind the scenes.

When I told Caroline I was writing this post she mentioned something I wanted to include:

"People will tell you it’s easy, but when you run into tough situations, it’s important to remember those struggles shouldn’t be a reflection of your self worth."

She’s totally right. Sure, the things I’m about to share aren’t fun to deal with, but being an entrepreneur means learning how to deal with them in a way that doesn't get you down.

I should probably throw a caveat here that our intention isn’t just to dump all our problems on you.  Our intention with a post like this is simply to give you some perspective for the problems you might be running into with your business.

In our opinion, so few online business owners are willing to share the rocky moments in between getting to the shiny moments. There are some people who don't want you to see them sweat. We're not those people, though. We want you to know when it gets tough because it gets tough for all of us, no matter how long you've been doing it for. 

Okay, onto all the sh*t we’re currently stepping in (or, more tactfully speaking, the things we’re trying to tackle and overcome to bring Wandering Aimfully to life)...

Working together

We’ve been collaborating in some form for nearly 7 years, but we're still always learning things about each other and how to communicate more effectively in our work. It's not always a walk in the park. We argue from time to time. We don’t see eye to eye on everything. We need our own space now and again. But… we still always come back together, remind ourselves how much we both believe in what we’re building and reaffirm that it’s best done as a team. (Also, wine helps.)

Giving up control

We can’t build Wandering Aimfully—the full vision we have for it, at least—by ourselves. We need an awesome front-end developer who can take our designs and turn them into functioning pages in our upcoming WordPress site. We need an awesome PHP/WP developer who can make our completely custom member dashboard a (virtual) living and breathing thing.

And while we appreciate everything these guys are doing to help us, relying on their skillsets means we are giving up control of our dream and our vision to them. This is not easy. In fact, some days it feels downright like torture for control freaks like Caroline and myself. There are lots of little (and some big) sacrifices we’re having to make throughout the development process to make our vision a reality, and those sacrifices feel even more painful because we don't have the power to determine what can be completed and what can't. We simply don't have the technical ability. When things take longer than expected, it creates a ripple effect for our to-do list and our deadlines. That part is especially frustrating, but it's all part of creating something that is better and more functional than your run-of-the-mill membership site.

Migrating existing users

Did we mention that we're moving over 400+ existing customers from a completely different place (former BuyOurFuture website) to our new member dashboard? That sounds like the kind of thing where nothing could go wrong, right? Yeah... not so much.

 We have no idea yet if our users will have to sign up again for our member dashboard (thou we're hoping not). If they do, how do we let them do that without having to pay? If they don’t, do they get to use their existing login and passwords? Can they reset an existing password they’ve never used in our new backend? What about any straggler canceled members we should have deleted but missed, and now have access to our new member dashboard? Something WILL go wrong with our existing customer migration and we simply have to try and prepare for that.

Being GDPR compliant

Uggghhhhhh. Caroline gets ALLLL the extra homemade biscuits and glasses of wine this week for digging through GDPR compliance docs and making sure we have a plan going forward so we're compliant. I’m horrible at following the rules and felt physically allergic to figuring out the GDPR next steps, so she spent hours hunting down resources to help us. This means adding extra work to our plates to update our Terms of Use, content upgrade forms, etc., something that isn't fun to do when our workload already feels overwhelming. But, that's a perfect example of a curveball you have to be ready to tackle as a business owner. 

Moving over our existing content

We’re going to have an entire other post about this process, but let’s just say that thinking about moving 400+ articles (some from WordPress and some from Squarespace) is making us feel a bit queasy. We have an Airtable sheet going for this (obviously) and have started the mental gymnastics (our warmup, if you will) that will be required to pare down older articles and combine ones with cross-over that we’ve written separately. Then, of course, we have to make sure all 400+ existing previous URLs map correctly to the new site...and try to do all that without downtime for those links. So...that's fun! 

Keeping up with our other businesses

Oh yeah, you guys know we have a few other businesses currently running, right? Some of these are tiny, and some are a bit bigger and require more time each day/week. No matter the size, we’ve realized they all take up real mental bandwidth, and that's a variable we have to contend with. As much as we want to be “laser focused” on Wandering Aimfully, sometimes an email here, or a customer support message there, will pop up and distract (read: DERAIL) us for a day or two. 

Supporting our existing community

We are extremely thankful to have such a supportive existing community (both in our email lists and in our customers for our many projects—specifically BuyOurFuture, which is now becoming Wandering Aimfully). Even though these folks have been incredibly supportive throughout this transition, it still takes a mental toll on us that we can't be fully present in the way we want to for them. The entire reason for cultivating the Wandering Aimfully community is to help members reach their goals and design lives around their values, and this means being available to answer every message and question we possibly can. However, when you're in "build mode" and it's just two of you creating a better future experience, there's only so much time and mental attention you can give. Right now we're being there as best we can while we button up this last stretch of the Wandering Aimfully process, but we're looking forward to the next season once the site and dashboard are launched so we can be fully available again.

Turning our brains off

Have you ever been waist-deep working on a project and find yourself waking up at 2am with a bunch of ideas of how to solve a certain problem (or maybe you think of a new problem which creates a mid-slumber-mini-panic-attack)? Yeah, we’re there. I’ve been thinking non-stop about Wandering Aimfully since we started, and a lot of those thoughts happen at 2:05am when I should be enjoying some deliciously restful REM sleep. Curse you, brain! 

Continuing to create valuable content here

If we’re being honest (and you know there's basically no other way for us to be) our content calendar and content creation has kind of gone to sh*t. What started as a well-crafted plan, with specific topics and a schedule all set nicely in place, has become the Wild Wild West of, what do we want to say that's feasible to get out the door this week?? We absolutely love creating content for this under construction site, but there is definitely a part of us that sees it as a thorn in our side at times. Don’t mention our Instagram feed please, we know it’s gone a bit quiet with new updates. Documenting the build of something, while building it, is just not easy folks. You have to prioritize and press pause where you can so you can turn your attention to what really matters in that moment–the product.

And then there's other crap

Things like making sure we have our captcha and recaptcha setup for the new site (and added to our forms). Having a plan in place to redirect all URLs from three separate websites when we go live. How we’re going to handle failed monthly payments when those start to happen. A trip we wanted to take in July, but probably can’t do as we’d rather not dent our cashflow. And I’m sure we’re forgetting about 30 other things that are random outliers at this point. 

Wowzers. We sincerely hope that didn’t come off as a ton of complaining.

It's just that we want to illustrate how difficult juggling all of this stuff can be. We want you to really see how it affects us so you don't feel so alone if you run into a similar list of frustrating things when you’re chasing down a big dream too.


We’re not letting this list get us down or slow us down. We’re acknowledging it. We’re pushing through it (piece by piece). And we’re doing our best to stick together and stay positive through all the less-than-awesome parts of this process. 

We know that in order to create something we've never created before, we have to encounter situations and challenges that we've never tackled before. It's all part of the process, and it will all be a part of the story of Wandering Aimfully. 

Design Decisions Part 2: Tear Down of Our Article Layout, Including the Welcome Mat and Sidebar

Design Decisions Part 2: Tear Down of Our Article Layout, Including the Welcome Mat and Sidebar

Build Diary: Week Seven (We Had A Fight, Then Recorded This Video Right After)

Build Diary: Week Seven (We Had A Fight, Then Recorded This Video Right After)