v3 Stuck? Let’s Unstuck!

Sometimes, the hardest part of the journey isn’t making decisions or solving problems — it’s that moment when you feel completely stuck. Like a turtle flipped onto its back, legs flailing, desperate for a nudge to get moving again. It’s frustrating, disorienting, and downright exhausting.

I know this feeling all too well. In the past few weeks, I’ve faced it twice: once in my role as Chief of Staff and once while testing my business idea on the side. Both times, I felt trapped in uncertainty, paralyzed by inaction. But I found a way to get unstuck — by trusting my gut, talking it out, and taking action, even when the path wasn’t clear.

If you’re feeling stuck, let’s explore how you (and I) can get moving again.

Stuck in Ambiguity: Crafting a Plan Without a Roadmap

At work, I was tasked with drafting the 2025 operational plan for our pre-product-market-fit company. In my previous roles, I had worked on annual plans for P&L with $20M to $250M in revenue. There were baselines to lean on, historical data to analyze, and benchmarks to guide the way. This time? I was staring at a blank slate. No metrics, no clear path — just potential and a lot of unknowns.

The questions felt overwhelming: How do we set goals when we’re still testing product-market fit? How do we allocate resources when we don’t know what “success” will look like six months from now? I tried gathering input from individual functional leaders, but their answers were fragments of a bigger picture that didn’t exist yet. What we needed was collective clarity — and that meant getting the entire ELT aligned.

But the ELT was stretched thin. Everyone was feeling the pressure to move fast, deliver results, and avoid overcommitting. The tension between urgency and realism was palpable. The ambiguity was suffocating, and each day without progress made the weight on my shoulders feel heavier.

Then my gut whispered: You can’t solve this alone. Bring the team together. So I did. We held a working session where we laid out the uncertainties and wrestled through them. We debated, disagreed, and sat in the discomfort of not knowing. Slowly, we started shaping a vision and defined milestones we could commit to, even if the details were still fuzzy.

The outcome out of the discussion wasn’t perfect, but it was enough to get us moving. I realized that in ambiguity, clarity doesn’t just appear — it’s something you create together, step by step. Even when the path forward isn’t crystal clear, taking action is better than waiting for the “right” answer to show up.

Stuck in Inaction: A Developer Holding Back Progress

While testing my business idea on the side, we were racing to launch our pilot. Our Shopify developer was responsible for setting up the subscription payment system — a core feature of our store. But progress was painfully slow. Out of four weekly meetings, three were rescheduled. One was canceled at the last minute.

Each delay chipped away at my confidence. Instead of discussing how to refine the subscription flow, we were stuck at square one. The urgency of the deadline was building, but our momentum was slipping away. I felt trapped between two bad options: keep pushing him or find someone new and risk delaying the launch further. My gut knew the truth: This isn’t working.

Letting him go wasn’t simple. I needed to align with my team, prepare the firing message, and deliver it over Zoom. My heart pounded during the conversation, but once it was done, the weight lifted. Briefly. Then came the follow-up emails, managing the awkward back-and-forth, and scrambling to find a new developer — all while juggling my full-time job and being a mom of two.

I reached out to the founder community for advice, interviewed new candidates, and asked sharper questions this time. We were able to found a better fit. The difference was immediate: clearer timelines, proactive communication, and steady progress. Instead of me pushing for scraps of effort, I finally had someone who pulled the vision forward.

I learned that getting unstuck often means making the call you’ve been avoiding. And when you’re stretched thin, capable partners aren’t optional — they’re essential. Talking it out and leaning on others can turn a paralyzing situation into forward momentum.

5 Practical Tips to Get You Moving Again

Reflecting on what helped me move forward in both situation, here are the 5 Practical Tips to get you moving again if you've ever get stuck.

1. Talk It Out 🗣️

When you’re stuck, your thoughts can get tangled like headphones in a pocket. Talking it out with someone else — whether it’s a colleague, mentor, friend, or fellow founder — helps untangle the knots. Saying things out loud brings clarity that endless internal thinking can’t. In both my work and side business, the moment I started sharing my uncertainty, new ideas and paths forward emerged.

2. Take the Smallest Next Step 🐾

Sometimes, being stuck feels like staring at a mountain, unsure where to begin. The solution? Don’t try to climb the whole mountain — just take the next tiny step. Break the challenge into the smallest, most manageable action. When I was drafting the operational plan, instead of aiming for the perfect strategy, I focused on scheduling the first working session. That small step led to momentum.

3. Trust Your Gut 🔍

Your gut often knows what needs to happen before your brain does. It’s that quiet voice whispering, “This isn’t working,” or “Try this instead.” When I was dealing with a non-committed developer, my gut kept nudging me to move on. It wasn’t until I listened and took action that things started to shift. Trusting your instinct is sometimes the nudge you need to get moving again.

4. Reframe the Problem 🔄

When you’re stuck, it might be because you’re looking at the problem from the wrong angle. Reframing can help. Instead of asking, “Why can’t I solve this?” ask, “What’s one way to make progress?” When ambiguity weighed me down while drafting the plan, I stopped asking, “What’s the perfect plan?” and started asking, “What’s a plan we can start with?” That shift in perspective made all the difference.

5. Take a Break, Then Reassess ☕

Sometimes, the best way to get unstuck is to step away for a bit. A change of scenery, a short walk, or even a night’s sleep can reset your mind. After the firing decision in my side business, I felt drained. Taking a short break helped me come back with fresh eyes, ready to find a new developer. Distance helps you see what you couldn’t before.

Stuck? Let’s Unstuck!

If you’re feeling stuck right now, remember: it’s temporary. Your gut probably already knows the next step, even if your brain is resisting it. And if the weight feels too heavy to carry alone, talk it out. Sometimes, the clarity you need is just one conversation away.

So, are you stuck? Let’s unstuck! I’d love to hear your stories, your struggles, or just offer a listening ear if you need one. Because getting unstuck is easier — and a lot less lonely — when we do it together. Feel free to reach out to me at JourneyWithSwings@gmail.com. Thank you for stopping by!

And for a little entertainment, here’s a video of a actual Tortoise stuck on its back on the beach then get itself unstuck. At 1:42, Tortoise made it! It's unstuck! 🐢✨ Maybe it's a reminder that sometimes all the efforts might seem pointless and not moving us anywhere at first, but then at THAT magic moment, you made it! Try out these tips. Let's unstuck!