Maybe the scariest outcome isn’t taking the risk. Maybe it’s waiting forever to feel safe enough to take it.
It can never feel like the right time to take risks and pursue the life you desire. What if you’re not waiting for the right time? What if you’re waiting for certainty?
The struggle between perfection and progress doesn’t just show up in my notebooks. It’s there every time I consider my creative career, too. Is it possible to leap toward a dream without having every detail secured? And what if waiting for the “right time” is actually holding me back?
In my last reflection, I wrote about moving from a rigid structure to a freedom approach in my bullet journal. But what happens when those same lessons about control, risk, and imperfection are applied to the way I approach my creative career and life goals?
The Psychology of Playing It Safe
It’s not just in my journaling that I’ve wrestled with structure and risk. In building a life and career in a creative space like film, I often wonder: is it even possible for someone like me? Someone without connections, expendable income, or easy access to key locations like NYC, LA, or London? I’ve been thinking a lot about the idea of pushing dreams back for the sake of responsibility.
I’m reminded of a ‘60 Minutes’ segment about women postponing childbirth to build stable income and careers. Their desire to be responsible parents is wise and deeply important. And there are real reasons to wait, and, of course, no one should leap into such a huge decision if it’s financially, emotionally, or physically unsafe. But what struck me was how society often frames there being a single “right” way or perfect time for everything. And how that narrative can make us afraid to ever take a step forward.
(p.s. This is not a comment on women’s reproductive choice, only an example of how I see this idea showing up in the world around me.)
The truth is there is ALSO risk in waiting.
How to Choose Progress Over Certainty
Sometimes, holding out for perfect conditions leaves more time for more problems and complications to arise. The same tension shows up with creative ambitions. I’m not condoning recklessness or ignoring real limitations, but I do want to challenge the idea that waiting for the “right” moment is always the safer or wiser choice.
What if the “safe” way is just as risky as pursuing your dreams now? Can pushing forward and taking calculated risks, even when the timing isn’t perfect, be safer in the end?
This is a delicate balance. No one can tell the future or avoid uncertainty, but questioning the rules about when and how we’re “supposed” to act can open up new possibilities.
As I wrote in my last reflection on control and fear, I feel the pressure to make responsible, cautious choices because I don’t have a safety net to fall back on. But I also wonder: what if leaping forward is exactly what leads to growth?
Although I’m still wrestling with these questions myself, I have found a few strategies that help me navigate the tension between responsible planning and taking action. If you’re facing similar doubts, here are some practical ideas that might help you move forward:
1. Start before you’re ready.
If you’re someone who finds comfort in structure (like I do), starting before you feel ready can be especially intimidating. The fear of making mistakes, or of veering off your carefully crafted plan, can make you hesitate. But the truth is, mistakes are how you discover what actually works for you. Think of your goal as a North Star, a direction, not a fixed destination. (This is a concept I stole from Ryder Carroll’s YouTube Video on setting meaningful goals.) With a perfectionist mindset, it’s easy to get caught up in striving for an ideal outcome or to interpret any misstep as a failure. But in reality, every imperfect action is a step closer.
It’s progress. And progress builds a life you actually enjoy, not perfect action.
Perfection is an illusion, and the “right time” rarely arrives. Take the next small step, even if you don’t feel fully prepared to make it.
2. Take calculated risks (the worst-case scenario is usually not that bad).
More often than not, the risks you imagine are less catastrophic than they feel in the moment. Other times, you’ll realize there are smaller, more manageable steps you can take that still move you forward. You’re likely overthinking it. When I catch myself overthinking, remember that progress doesn’t require certainty, only a willingness to try with my whole heart.
But small steps forward are much harder to take when you’re rigidly attached to a specific end result. It’s great to be ambitious, but you don’t have to plan every detail before you move. Leave some space for detours and surprises.
Interstitial journaling has really helped me here. It lets me notice where I get stuck or hesitate and spot the next small step I can take, even without a perfect plan. Sometimes, that’s all you need to keep the momentum going.
3. Build a flexible structure.
Create routines or systems that support you without boxing you in. Honestly, this has been (and continues to be) one of my toughest challenges. I love outlining a beautiful routine, but following it is another story. The routines I build tend to get restrictive and rigid fast, which can end up holding me back from real progress.
As I mentioned in my last blog post, sometimes strict structures can stifle creativity rather than help it flourish. I’m learning to design systems for myself that leave space for a little messiness and creative chaos.
What kind of scaffolding do you ACTUALLY need to move forward on what matters most? Give yourself permission to experiment, make mistakes, and pivot when things don’t go as planned.
A flexible system is key to being able to do this.
And afterward, pause to reflect. What worked? What didn’t? Use those insights to guide your next move.
Ultimately, the pursuit of the “responsible” path can lead to missed opportunities; sometimes you have to leap before all the details are in place. The balance isn’t about being reckless, but about giving yourself permission to move forward even when the path isn’t perfectly paved. If you’re waiting for everything to be certain, consider: what might you gain by starting now, imperfectly?
The Blank Thought
Creativity has never asked us to predict the future. It asks us to be present enough to notice, and brave enough to respond. Every creative act begins the same way: Not with certainty, but with a decision to begin anyway.
— Ryn Elizabeth
This is part of a series on letting go of perfection and embracing creative risk. The next post is coming next Monday!
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