There’s something undeniably appealing about a fresh start. We feel it at the beginning of a new year, but also in many other moments: a new week, a birthday, the first day back after time away, or any other marker that lets us believe some previous period has closed. Researchers have described this as the fresh start effect, the tendency for temporal landmarks to make our aspirations feel a little more available to us. In those moments, the clean slate feels real, and beginning again can feel energizing.
Psychology Today’s recent cover story, “The Best Ways to Begin Again,” explored this tension beautifully, making the case that beginning again can be good for us precisely because it asks us to enter the vulnerable state of being new at something. Novelty can wake us up. Beginnerhood can stretch us. First attempts can remind us that we are still capable of change. But the same qualities that make a beginning powerful also make it fragile. Being new at something usually means tolerating mistakes, awkwardness, and uncertainty long enough for the experience to become meaningful. When the novelty wears off, the pursuit is not quite what we expected, or life interrupts the way we imagined things would unfold, often our initial plan can break down.
The Part After the Plan Breaks
I was recently fortunate enough to sit down with Steve Kamb, author of How to Try Again and founder of Nerd Fitness, to discuss this topic. Kamb has spent years thinking about behavior change in the place where most advice tends to get thin: after our best intentions meet real life. One of the things I most appreciate about Kamb’s ideas is that he doesn’t treat failure as a character flaw. He’s much more interested in what happens next: how we talk to ourselves after a missed day, how we decide whether something still matters, and how we make it easier to come back without turning the whole experience into a referendum on who we are.
In our conversation, Kamb described a day so busy that you miss the opportunity to shower. Almost no one in this situation would convince themselves they’re “bad at showering.” You don’t go buy a shower journal, hire a shower coach, and promise to reinvent yourself next month. You just take a shower the next day.
It’s illuminating because it highlights how punitive we can be with ourselves when our plans get messy. We miss a workout, and we make the missed workout evidence of failure. We cannot write for a week, and the pause becomes a character flaw. We drift away from a favorite hobby, and abandoning it starts to feel easier than returning to it.
A useful design question, then, is whether the thing we are trying to sustain has a desirable path to reentry. A plan’s path is not only logistical; it is often emotional. Even when we know what to do next, the activity becomes harder to approach when it is attached to a real or perceived shortcoming.
Enjoyment as Part of the Design
Unfortunately, when it comes to motivation, fun is often treated as an afterthought. We focus on discipline, tell ourselves or our clients and patients to trust the process, and assume the eventual outcome will be enough to keep us going. But if the only thing pulling us back is obligation or a future benefit, trying again becomes harder than it needs to be. When the process itself is enjoyable, returning becomes more likely.
What does that look like in practice? It might be the infectious social energy of a group fitness class; the satisfaction of small, visible wins early in the process; or the creation of an enjoyable ritual (e.g., listening to a favorite audiobook while you do the work). These are small design choices, but science informs us they matter because they increase the desirability of the activity.
Finding enjoyment early matters because many worthwhile pursuits are not especially rewarding at first. Early progress is often uneven. Our first attempts can feel clumsy. And if the only reward is months away, the first disruption holds a lot of power. In this context, a little immediate enjoyment doesn’t make our pursuits shallow; it simply gives them a better chance of surviving contact with real life.
Fun Is Not the Opposite of Effort
This is an important distinction because fun is sometimes misunderstood as the opposite of effort. Many of the most meaningful forms of enjoyment actually require effort. Learning a skill, getting stronger, or taking on an activity that stretches us can be deeply enjoyable, even when it isn’t easy. In my own work, I think of these as living activities: high-effort, high-reward pursuits that help us feel more engaged.
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The problem is not that these activities ask something from us. In fact, that’s often part of what makes them satisfying. The problem comes when we strip away everything that made the activity feel alive and then expect discipline to carry the whole load. A hike we used to enjoy becomes something we now do only for the steps. A creative practice we used to love becomes something we now do only for output or acclaim. The activity may still be “good for us,” but the inner enjoyment and intrinsic motivation start to disappear. Once that happens, returning after a break becomes harder because we’re no longer returning to an experience. We’re returning to a standard.
Contrary to what some believe, designing for enjoyment is not the same as making things easy. It is about preserving enough pleasure, curiosity, connection, and/or play within the pursuit so that it remains psychologically approachable. The enjoyment doesn’t have to be grand. It just has to be present enough that the activity gives something back before the long-term payoff arrives.
Fun Brings Us Back
When we’re already fighting the inertia of starting again, the last thing we need is more unpleasantness. Sometimes that means returning to the part of the activity we genuinely like. Sometimes it means making the experience social again. Sometimes it means allowing the first return to be imperfect enough to be enjoyable.
Our reentry into something meaningful is unlikely to be its best version. It may be awkward, slower, rustier, or less satisfying than we remember. But if the goal is to return rather than to perform, that isn’t a failure of the process. It is the process. Fresh starts help us imagine a better version of ourselves, and that’s part of their appeal. But if we need a fresh start every time life interrupts us, the system is too fragile. A more durable approach is to build pursuits that don’t require a clean slate to resume.
That may be one of the most practical uses of designing for fun: Fun gives us a reason to return before we feel fully ready. The goal is not to design a life where nothing ever gets interrupted. The goal is to design a life in which the things that matter to us have effective mechanisms for drawing us back.