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When Do You Shut It Down and When Do You Keep Going?

Wandering Aimfully Through Failure

When Do You Shut It Down and When Do You Keep Going?

And how do you navigate the murky waters of having your identity tied to your work?
Jason ZookJason Zook Jason ZookJason Zook

Written by

Jason Zook

Is there a project or idea you’re working on right now that you feel you’re at a crossroads with?

A few years ago I loved the idea of creating small software products. In fact, I remember when I started thinking about leaving the 9-5 world in 2005 and dreamed of being a “software startup founder.” The stories of successful venture-funded startups and crazy monthly revenue seemed otherworldly to me.

Fast forward to 2013 and I started working on my first web application (I am going to interchangeably call them web applications, software products, web apps, whatever… it’s all the same to me!) Then in 2015, I had a second web app. In 2016 a third. In 2017 a fourth and a fifth.

Uh oh, you can probably see where this might be headed?

Truthfully, I don’t have any regrets about starting too many software products. I was able to partner with great, talented co-founders, and I enjoyed working on each project.

But here’s the real-talk for you…

Starting anything from scratch, no matter how much experience you have in another area (or in that same field) is always going to be its own unique uphill climb.

Take ofCourseBooks, for example. It was (and still is) a very simple embeddable workbook product.

The idea was to mesh Typeform and note-taking together and to help online course owners give their students a more effective way to consume their teachings.


My co-founder Paul Jarvis and I had a combined audience of over 100,000 people between our email lists and social media followings. We also had a popular podcast (3,000 downloads per episode) where we publicly built the app and found our technical co-founder (hi, Zack!) Paul and I have had solid success selling online courses and other products over the years.

Yet, the best we could do was get ofCourseBooks to around $2,000 monthly recurring revenue (MRR). And we pushed it pretty hard for a few months.

While we were happy to have a side project that didn’t take a ton of continuous effort on our parts, we had certainly hoped it would generate more revenue. We didn’t even have wildly ambitious financial goals, we simply hoped we’d get to $10,000 MRR.

This is a similar story for me with almost every software product I’ve built. They are able to generate some monthly revenue but it’s never enough for one of them to earn the majority of my focus. And there’s another problem…

I’m not sure I’m cut-out to only work on ONE product for an extended period of time. I’m tired of beating myself up about that.

I understand the blueprint of how to make a software product successful. The issue is that I know it’s not the type of work I want to be doing all the time:

There are probably 20 more bullet points I could list out and that’s precisely why I don’t think I’ll ever run a software company as my sole gig.


What Happens When Your Identity Is Tied To Your Work?

It gets even more challenging to shut down a project or keep going when your identity is tied to it in some way.

If you’re reading this article then your work is probably tied to your identity in some way. Your name is associated with your product or you ARE the product (hello designers, artists, developers, any freelancers).

It’s especially tough to make a decision about moving forward or shutting down an idea when you feel a strong connection to it.

There’s a certain amount of fear that comes along with shutting down a project that isn’t serving us. Kristen Yates, a member of our Wandering Aimfully community talked about it like this:

When I tap into this fear of letting go of a project there’s often something around an identity I’ve attached myself with around it in addition to the time/resources/energy sunk in. It makes me curious to explore what that fear is about? What it means to let go of something that we may have attached with beyond it simply being an income source or even a passion project? What about when it becomes a part of who we are?

Kristen is totally right and brings up some really valid questions. This has been a struggle for me with many of my projects over the years.

What happens when a project becomes part of who we are?

If you quit something that’s fundamentally tied to who you position yourself as to the outside world you can feel trapped. If you say you’re a designer, but stop being a designer, will everything think you’re a fraud? Will they question what you “pivot” to next because it’s unfamiliar and different?

There’s no easy answer when it comes to dealing with the fear and the identity crisis that can come with pouring ourselves so deeply into our work.

I’m not willing to stay trapped working on one thing or one idea for the fear of what other people might think of me. I don’t think you should stay trapped either.

If people don’t respect change and don’t see it as necessary, they’re not people I want to surround myself with. And sure, we can’t control what people say or think about us, but we shouldn’t be focusing on that anyway. You have to focus on what you can control and if that’s making a big change in your life or business, then that’s a perfectly acceptable decision.


Do You Always Feel Like You’re On The Edge Of Success Or Failure?

No matter what type of product or idea you’re building, it can feel like you’re always on the edge of success or failure.

The Edge of Business

Does this edge feel like success or failure to you right now?

We, as business owners, have this thing when it comes to our creations. They always feel like they might be on the cusp of taking off and therefore it’s so much harder to let go of them.

And then there’s the other side. Things could crumble at any moment. Yet, we’ll hang on for too long due to sunk cost bias. You know, spending countless hours, days, weeks, months, and even years on an idea and not wanting to throw all of that away for fear of “failing.”

We need to quit projects that aren’t serving us any longer to create space for new things.

Or, you know, just create space and NOT IMMEDIATELY FILL IT. (That’s as much a note to you, dear reader, as it is to future Jason).

For me, and maybe for you, it’s important to sit down and really weigh the options with whatever you’re currently working on that isn’t bringing you the value you’d hoped.

Value = Revenue + Enjoyment

During the past year, I’ve decided that I’m not going to keep dragging projects along if they aren’t bringing me value. The revenue isn’t the most important indicator, in fact, it’s probably a dead-tie with enjoyment.

And let’s be honest, we all probably have a project or two that sucks our time and attention away, while not returning much value back.

Where do you REALLY want to be spending your (work) time?

That’s the question I keep coming back to. I love the thrill of creating a new software product. I love working with talented people and bringing an idea to life. I enjoy a little bit, the challenge of getting people to make the initial purchase. But things start to fall short for me when I feel I’m constantly chasing after growth, even a small amount of it.

I’m in my “zone of genius” when I’m doing weird things. When I’m creating projects that make people tilt their heads and sharing ideas that feel completely unique to me. The problem is, not all of those weird projects can pay the bills on a consistent basis.

So how do you find the balance? What’s the answer?

I’m sorry to be the bearer of bad news, but it feels like there is no ONE answer (to rule them all). It feels more like we all need to understand working for ourselves is an ongoing and ever-changing process.

You might be reading this and have found your ONE thing and you’re kicking major ass with it. Awesome! If working on your idea brings you value and you don’t feel trapped by it, you should absolutely keep going. You should acknowledge the path to success will be a winding one and you may never reach an actual finish line. Enjoy the bumps along the way, they’re only going to provide invaluable lessons and moments where you can improve and get better.

However, for a lot of us, the answer may not be to keep going, it may be time to shut a project down.

Give yourself permission to gracefully exit a project (whether that means making some money or $0.00).

A special thank you to Reed and J.P. who are the owners of two web apps I co-founded.

Slowly but surely I’ve realized that I can’t manage and run five different software companies.

It’s actually not even the marketing and time investment that’s the issue, it’s the mental toll it takes to keep track of all of them (shocker, I know).

I’ve started giving myself permission to sell-off or shut down projects that aren’t bringing me value.

I had two successful “exits,” as they say in this business. Those exit amounts won’t impress you, and truthfully, that’s not really the point of this article. I do want to acknowledge that I’m grateful to have a community around me that believes in the products I’ve built and are willing to invest their money and continue working on those ideas.

Removing projects from my virtual plate is not only creating more time for new ideas (or existing neglected ideas) but shutting down projects is also helping to create mental space I didn’t even know I was missing.

There’s an underlying layer of stress when we continue to carry projects along and not make a decision to move on from them.

My hope is that this article helps you move on from an idea you may feel stuck with. Some app or thing that you feel you can’t stop working on because it was so close to finally being worth all the time and energy.

So, what will it be for you? Are you shutting down or pushing forward?

When Do You Shut It Down and When Do You Keep Going?

(Big Fat Takeaway)

Chasing your big idea or dream is difficult but it's important to understand when you should keep going or when you should be okay with moving onto something else.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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