How did I end up wasting so much time and getting absolutely nothing done?
What should I even be working on?
Why is this so hard?
These are the questions I’ve been asking myself a lot since going off on my own. No two days are the same in the world of business. I used to imagine that making the leap would be a life-changing experience, that things would just start falling into place, and I’d know exactly what to focus on and how to spend my time.
But since starting my own ventures—Houndthem.com and DugDugStudios.com—I’ve had to get serious about planning. I’m trying to prioritize tasks that truly matter, the ones that move the needle toward generating revenue.
One reason for this shift is everything I’ve read about how 20% of the effort yields 80% of the results, so focusing on the right things really counts. Plus, I’ve never been the most organized person. I’m the type to forget little things like picking up groceries, scheduling a doctor’s appointment, or fixing the broken water dispenser on my fridge.
Up until now, this “organized chaos” approach worked fine. I reached a place that many would consider successful: a $200K+ salary, a home, a rental property, a paid-off car, no student loans (just saying for context, not to brag). I never questioned this method.
I’m not a natural planner, but they say, “To achieve things you’ve never achieved, you need to do things you’ve never done.” So I thought, maybe I should start being intentional with my energy and try planning.
That’s where the idea of focusing on big, impactful tasks came in. I began mapping out my major to-dos, working on only those for each day. If I wrapped up in three hours, I’d stop for the day.
But then, doubt would creep in. I’d think about the hundred other little things I could be working on and question if I was on the right track. I’d then feel anxious that what if everything I was working on ended up being a waste of time. This cycle would repeat, causing me to be the least productive I’d been in months.
This journey has led me to a few key takeaways about myself, planning, and entrepreneurship:
Get Comfortable Being Uncomfortable
If you constantly feel out of your depth, you’re probably headed in the right direction. It’s normal to feel imposter syndrome; the key is acknowledging that uncertainty and pushing forward rather than retreating to what feels safe.
Play to Your Strengths, but Improve Your Weaknesses
I know I’m not a natural planner, and that’s okay. When I over-plan, I’m less effective, and it feels more like a chore. However, I’ve started identifying small changes that help me improve as an organizer and planer, like automating tasks that make me feel overwhelmed.
Trust Your Gut
You won’t always know if you’re working on the “right” thing, so don’t overthink it. Deep down, you probably know what you need to focus on. Go with that instinct and keep moving forward.
Bonus: Brain Dump Method
One strategy that’s helped is doing a brain dump of everything I could work on for Houndthem.com and DugDugStudios.com, from landing pages and SEO to content, blogs, newsletters, and more. When I feel stuck, I pick something off that list, finish it, and use the momentum to keep going.
In the end, my biggest takeaway is this: Don’t overcomplicate things. Planning and structure will have their place, but it’s rarely crucial in the early days. Enjoy the process, and keep moving forward.
