With my own business I’ve experienced just about everything you’ve mentioned here. We are explicitly not seeking hyper growth, and we are fine with the “traditi

With my own business I’ve experienced just about everything you’ve mentioned here. We are explicitly not seeking hyper growth, and we are fine with the “traditional” approach that says “businesses take {three,five,seven} years to become profitable.” From a financial perspective my cofounders and I aren’t doing this to get the 45,000 square foot mansion in the hills overlooking Veil. We just want to use our skills to do something that helps other businesses as a means to building a tidy retirement nest egg. Several family members have done that same thing in each of our families in the past. And yet we’ve still fallen into some of the same traps any startup in technology falls into. We recently decided to exit the Atlassian ecosystem (prior to their recent issues) and have been doing so while we’re still under the grandfathered pricing for their cloud offerings. We didn’t want to wait until the last minute. We bought ourselves some time so we didn’t want to rush it either. Just deciding to step back and replace tooling can be difficult. It means you’re tying up a LOT of cycles in internal work, but sometimes that’s a good call to make. We had been using Jira for anything “taskable” but we have both internal/code work and external/billable work, and we weren’t managing either very well in Jira. It’s easy to say “we will lose a lot of history and velocity” but you can export data, and the velocity you lose continuously by not using tooling that works for you, can be much more harmful. It can be difficult to SEE that you need to step back and reevaluate something as big as your tasking or documentation management. For us, we decided to use this as an opportunity to look with fresh eyes at everything and ended up replacing virtually all of our tools and infrastructure. We even replaced all but one core AWS service in our application and moved everything else to Linode. We replaced our billing system too. We moved from Chargebee, which was vastly over complicated for our current needs to the point where we hated using it, to using pure Stripe and project management with ActiveCollab. We said no to some business while we did that, but from the inside perspective our lives are much easier, our revenue cycle is more consistent and manageable (and actually -happens-) now that our billables are in a revenue-aware tasking system (ActiveCollab) instead of a pure-task tracking system (Jira). We’re OK with taking our time because slowly we’ve been seeing just how to build this business effectively, and for us that’s far more important than scale or quarterly returns right now.