"How do I get my groove back?"

📨 Ask An Ex-Planner

Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.

Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.

Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #13. ✨

☀️ How was your week?

Evening views from our Airbnb

I spent last week in Vancouver with my dad and stepmom. We enjoyed a variety of Vancouver’s Greatest Hits: strolling the Stanley Park seawall while watching seaplanes take off, eating soup dumplings more days than not, and staring at the aquarium’s resident otters for hours on end. And we skipped town, too, for side trips to Squamish (an outdoorsy paradise) and Victoria (an extremely walkable city that feels distinctly European).

Scenery from the VanDusen Botanical Garden

It was my first time in British Columbia since the pandemic-era border closures lifted, and it felt so good to be back—especially because I got to share it with people I love.

On to today’s letter!

📨 Ask an Ex-Planner

Life is full of change, transition, and uncertainty—all things that are better navigated together. So in this column, I hand over the mic in order to address what you’re struggling with or curious about.

Want me to respond to your question? Make an anonymous submission right here—or just reply to this email.

Dear Maddie,

Do you have any advice when it comes to rebuilding your confidence after a setback?

I went through a hard time recently, and was surprised by how much of a hit my confidence took, in addition to dealing with the situation itself.

Dear reader,

I feel your pain acutely. Your question transports me to the beginning of my separation—a time when I felt more unsure of myself than ever before.

In my experience (and perhaps yours, too), it doesn’t matter what led to the end of a relationship: who played what role, the specifics of the breakdown, how either of you tried to fix it. A breakup can be full of kindness and compassion, and your confidence still takes a nosedive.

New fears slip into your consciousness: Am I unlovable? Is there something fundamentally wrong with me?

At the same time, I was navigating the early stages of a promotion. Transitioning from associate financial planner (a behind-the-scenes job with lots of detail-oriented, technical work) to lead financial planner (a client-facing role involving leadership and big-picture conversations) wasn’t a setback. On its face, it was a huge step forward in my career. But the nature of my work had fundamentally changed, requiring a skillset I hadn’t yet developed, which—at least in my case—was a recipe for impostor syndrome.

It felt like the perfect storm of confidence-killers.

At first, I tried to rebuild my confidence by reading about these particular life transitions. I devoured books that helped me better understand my relationship challenges, and taught me the skills I’d need to level up at work. I applied that new knowledge, put it into practice.

It was a profoundly useful approach for my education—for my personal and professional growth—and it did absolutely nothing for my confidence.

Amidst these moments of transition, I stumbled upon this profile of writer and strength-training evangelist Casey Johnston. For reasons that I don’t remember with perfect clarity—probably because I really needed a distraction—I developed a single-minded obsession with learning to lift weights.

I tore through her Couch to Barbell ebook in less than 24 hours, bought a pair of adjustable dumbbells, and learned the basic movement patterns. With each passing week, I found myself using progressively heavier weights.

Within a few months, it became clear that if I wanted to progress further, I’d need to start working with a barbell—an intimidating proposition.

Fortunately, it was a solvable problem. Once a week for the next six months, I paid a personal trainer to teach me the ropes.

I didn’t have the right shoes at first, had no clue how a squat rack or cable machine worked, and my form was shaky AF. I didn’t know how to structure my programming. Getting adequate protein and calories were new-to-me considerations. But with each passing week, I addressed one or more of these challenges, and my “Strength-Training Topics I Find Overwhelming!” list steadily grew shorter.

All the typical confidence-building how-tos (“Do power poses!” “Fake it till you make it!”) are attempts to address confidence deficits directly. None of them worked for me.

What worked? Something completely unrelated, something I hadn’t begun in order to build confidence at all, but something that did remind me of my power: learning how to squat, deadlift, and bench press.

Lifting weights had—mentally, more than physically—transformed me into the superhero-movie version of myself.

Here’s what I’ve learned about building confidence, primarily through trial and error.

✅ Direct confidence-building schemes don’t always work—and you might be surprised by the indirect ones that do.

I’m not suggesting that you take up powerlifting (although it might be worth a try!).

What I am saying is this: if you live long enough, you’ll experience setbacks in many, if not all, aspects of your life. It’s important to face those challenges head-on and make necessary improvements. For me, there was no substitute for going to therapy after my separation, or getting more professional education after being promoted.

The problem? Healing work and skill-building aren’t always direct lines to confidence. And even when they are in the long run, you’re probably looking for a confidence boost right now—because it feels good, and because it keeps your motivation high for the necessary longer-term work required of you.

✅ You’re an integrated system.

You’re not just a floating mind; you have (you are) a body. You’re a spiritual being, and a creative one. You’re a member of different relational systems that affect you profoundly: a family, various circles of friendship, maybe a romantic partnership, plus communities built around your profession, volunteer work, and hobbies.

A change in one part of the system impacts the others, in ways large and small. That can be used to your advantage: if you’re challenged, battered, or weakened in one arena, ask yourself what other aspects of your life can reasonably be attended to, healed, or strengthened.

✅ Perhaps your best bet? Pursuing an empowering task or project…in a totally separate arena.

A physical pursuit worked for me because my crises of confidence happened in the relational and professional realms. If your health is suffering, maybe it’s the perfect moment to lean into your mental prowess or spiritual life, or devote extra energy toward your most supportive friendships. 

Success in an arena that isn’t emotionally charged will probably make you feel like a badass, capable, accomplished, or lovable, all of which pave the road to confidence.

✅ Ask yourself: do I need a big challenge, an easy win, or something lighthearted?

Decide ahead of time what kind of effort is most likely to boost your confidence; you probably have a gut feeling, and that gut feeling is probably right.

Maybe it would be better to do something challenging: training for a race, keeping your garden alive (the struggle is quite real over here), or starting a Substack. Applying yourself to a high-stakes or long-term project is a reminder that you’re a capable person who can do hard things.

Or perhaps an easily-achievable task would be better if you’re feeling fragile—if the possibility of another setback in a new area would be demoralizing. Building confidence can look like taking on one easy win, then another, then another. It’s like baby-stepping your way back into feelings of self-efficacy.

And don’t forget to consider something that’s just plain fun (fostering kittens, anyone?) because lightheartedness leads to taking yourself less seriously—which feels strikingly similar to confidence.

✅ Sometimes, a prolonged lack of confidence is a signal that something’s amiss.

When you’ve addressed your challenges head-on, and tried all the suggestions above, an unabating lack of confidence might be a hint that you need to reevaluate things big-picture—that something is out of alignment, perhaps even calling you to proactively set your plans on fire.

One Sunday morning, at my local run club, I found myself jogging alongside someone who’d recently beaten breast cancer. She’d been a competitive triathlete; now, as we completed a fourteen-minute mile together, she was celebrating the fact that she had the lung capacity to run at all.

She told me about the leadership training that served as a lifeline during her recovery; it allowed her to grow in her career even as she waged a grueling physical battle.

She talked about her church community—the spiritual teachings, and the friends she’d leaned on there. One of those friends had prodded her to show up at run club for the first time that week.

As we jogged, we gazed out over the Puget Sound, and she expressed profound gratitude that we were there together that morning, enjoying the sound of the lapping waves, the colors of the sunrise, and the seals that periodically popped their heads above the waterline.

I was struck by the physical challenges she’d just experienced, as well as her confidence as she returned to physical activity.

I shouldn’t have been, though. She’d built scaffolding in so many other areas of her life, all of which buoyed her, carried her through.

💬 What do you think?

I’m curious to hear from you. What would you like to share with the reader who wrote in?

Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.

Warmly,
Maddie