Tackling the Big Challenges: Case Study with Timing

by Katie Joll

Have you ever reached a point in your business where things are going smoothly, but you feel that it’s time to take the next big step or upgrade?

These are often the daunting things, the tasks that will challenge or stretch you, but you know that you can’t just sit comfortably at the status quo. You need to tackle that challenge so that your business reaches the next stage of growth.

On a recent podcast, we spoke with Timing founder, Daniel Alm about how his business has grown up and what he has done to fuel that growth. One theme that came up was taking on those big, perhaps scary challenges.

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The big challenge…

Daniel, like many other tech founders, started Timing from scratch as a way to resolve his own challenges with tracking how he spent his time. This began in his university days back in 2011, growing to the point Daniel was able to work full time on Timing from 2016.

After launching Timing 2, a new and improved version of the app in 2017, Daniel realized his next step to continue the growth of the app: 

“Many customers had inquired about the ability to sync their time-tracking data across their Macs, for example, between desktop and laptop,” says Daniel. In addition, I knew that I would want to do a web app, a Zapier integration, and maybe even an iPhone app later on, and all of those would need a working sync system as a prerequisite.”

As Daniel explains it, a sync might sound like a relatively simple solution, however the building of it is a complex challenge. “Building a sync is very challenging,” he says. “There are so many different things you need to get right. For example, you don’t want to lose user data and you want to make sure you create a consistent experience for your users. This is a lot more complex to build than it sounds.”

Daniel adds; “Building the sync stretched me out of my comfort zone, but it was something that I knew I had to do to help grow Timing. The sync itself was valuable to users, and it built the foundation to enable the web app and API.”

Screenshot from Timing

Tackling the challenge

Timing is self-built and self-funded by Daniel, so building the sync was a task that he was going to have to take on too. Given that it was stretching him so far out of his comfort zone and that Timing was already successful, how did he stay focused and stick with this task?

It turns out that meticulous planning was the “secret” behind what kept Daniel going. “Before writing any code, I wrote a document outlining exactly how the whole sync process would function,” he says. “That served as a great reference for the function, and ensured that I would not accidentally change the behavior during the implementation, which could have caused incompatibilities and problems later on.”

Daniel also subscribes to the idea of breaking big goals down into bite-sized chunks, enabling a stepped approach. “I also created an outline, listing all the individual steps I would need to build for the sync system to work,” he says. “That amounted to possibly hundreds of steps, but it also greatly helped me stay on track and measure my progress.”

According to scientific analysis, breaking goals down into smaller steps is exactly what we should be doing if we want a better chance of succeeding. There are a few reasons for this, such as:

  1. Our working memory, the part used to complete mental tasks, can only cope with three to five items at once. If you were to rely on memory alone to get through everything, you’d be pausing frequently to ask yourself what the next step is. At any time that you pause, it’s an opportunity for distractions or going off-task.
  2. Breaking tasks down gives you more regular gratification. If you’ve ever experienced a “rush” at being able to check something off your to-do list, this is the brain chemical dopamine at work, which is connected to pleasure and motivation.

    As humans, we’re programmed to want more of that, so we’re more likely to keep going when we get those regular feelings of gratification. It’s an important part of what scientists call “self-directed learning,”, where dopamine triggers you to try and repeat the success that leads to the rush. 
  3. Breaking down tasks helps you to be very specific about your goals. It explains your goals in micro-terms which helps to increase your focus. Researchers have found correlations between goal specificity and level of performance.

In all, the sync took around six months from start to finish. Daniel consulted with a developer friend for parts of it, and carried his stepped approach through the sync project, including for testing; “I wrote a lot of tests while implementing the sync system,” he says. “That enabled me to essentially build the entire client-side sync system (and verify that it would work in practice) before I even started work on the sync server. That worked great; the first sync worked almost immediately right after putting all the work of the previous five months together, without needing adjustments.

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Lessons to take forward

As Daniel describes it, one of his biggest lessons was in learning about his own capabilities. “Given enough time and with a methodical approach, I can tackle almost any engineering problem for Timing. It might take a while, but eventually if I chip at it, I can build it,” he says.

The result of Daniel’s planning and effort to build the sync was a very reliable feature and some extra-happy users. Daniel says that leaping that hurdle and building a robust sync unlocked new opportunities for Timing, such as the building of a web app that is now available. “Building the sync gave me confidence that other problems are not too difficult to solve,” he says.

Taking that step has also opened up Timing to a broader audience, which is not always easy to do. “The product needs to be there,” Daniel says. “It needs to be suitable for your new audience, while still being valuable for your current customers. You may need to adjust your positioning a bit, but that doesn’t mean you abandon your current audience.”

To any founders who may be weighing up whether to tackle a daunting task for their business, Daniel says; “just think it through really well and make sure that you have a good plan. You don’t want to be caught unprepared in the middle of such a daunting task.”

Sometimes the planning will take you more time than the actual execution, but having those steps broken down can make the difference between initial success, or having to do a lot of rework. You know that old saying, “proper planning prevents poor performance!”

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Final thoughts

Sometimes, even when your business is running comfortably, it’s time to up the ante and take the next step for growth. 

While this can be a daunting challenge, taking the time to break it down into steps is a great way for anyone to tackle the big tasks. We often want to do things as quickly as possible once we’ve decided they need to be done, but Daniel’s experience highlights the benefits of taking a methodical approach.

Importantly, once you’ve successfully completed that challenging task, you often come away with a blueprint for next time. As Daniel said; “I’m confident I can use this process to work through the next big task for Timing.”