The Digital Update: Making Progress in an Endless Game
May 19, 2026
It’s easy to feel lost in the endless game that is entrepreneurship, but with the right mindset and tools to help you track your progress, you may find that you’re farther along in your journey than you think…
It's your weekly dose of clarity and insight on all things tech & business from Dream in Digital! Each week, I'm here to share my thoughts to help you make the most of today's technology and build a business that genuinely supports the life you want to live.
This Week’s Core Focus:
Understanding the Entrepreneurial Journey
Lately, I’ve been reflecting on and really feeling a core truth that every entrepreneur eventually hits: this path is incredibly messy. Especially for a recovering perfectionist like myself, this realization is heavy. I’m proud of putting myself out there and making the progress that I have for Dream in Digital over the last few months, but if I’m being completely transparent, it still feels crazy, unpredictable, and frankly somewhat exhausting & defeating at times…
We look around and it’s like everyone is selling some kind of “cheat code,” playbook, or 20-step map to success, but the reality is that there really isn’t a game plan that guarantees success. It’s simply a matter of showing up every single day, giving it the best you have, and adapting as you go to hopefully figure out the next stage — while simultaneously “winning” the stage you’re currently in.
I’ve always had a love for sports, so hopefully this repeating, 4 step analogy can help us gain a better understanding of the journey that is being an entrepreneur…
Practice: A team doesn't just practice in the pre-season; they practice every single week to stay sharp, and to correct their mistakes. In business, this is the continuous prospecting, client out-reach/management, and other internal operations you need to be doing to keep your business running and growing “behind the scenes.”
Preparation: Before every game, teams scout their opponents and create a plan for success. In business, this more so becomes about understanding your ideal customer, and helping your clients study & understand their unique value to their customers. When your business can continually solve people’s problems, that’s how you “win.”
Execution: No matter how good your game plan is, the game is often fluid and unpredictable. You have to make adjustments on the fly. The same can be said in business. You must show up and continually deliver for your clients and your own company, regardless of the circumstances. Adaptability is paramount to success!
Recovery: You can’t keep going at 100% all the time. Every good coach manages their bench, and even elite athletes prioritize rest so that they don’t burn out mid-season, or even mid-game! You need to treat yourself the same way. Do good work, respect your boundaries and get good rest, and then come back and repeat the cycle — shift after shift.
Tech Tip of the Week:
Your Task List As Your Track Record
The Problem: Unlike a sports game with a clock, a score, and even standings for the team to look at throughout the season, business is an endless game. So, how do we keep track of our progress while playing a never ending game?
The Solution: One of the core ways to do this is through reflection and goal setting. I’ve talked a few times before about big-picture planning and reflection, along with longer-term goal setting, so I want to dive more into the “game within the game” and how you can use your Google Task List to track your Weekly Goal Progress and maybe even more importantly, your Overall Output.
Log: Use Google Tasks to log all of your work tasks across all your clients & business divisions.
Schedule: Schedule the top tasks you need to complete throughout the week.
Star: Before you begin each day, star the top tasks you need to complete for that day.
Complete: When you’re done with a task, do NOT delete it! Simply check the task off as “Completed.”
Review: At the end of the week, look back at your “Completed” tasks to see how much you were actually able to accomplish.
How This Helps: By having a clear log of what you were able to accomplish throughout the week, you allow yourself to see the tangible, detailed, progress that you’re making on your journey. This also allows you to make any needed adjustments to how you work, or simply just avoid the “I’m not working hard enough” trap that often plagues entrepreneurs.