"How can I give and get help during tough times?"

📨 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 #9. ✨

☀️ How was your week?

I watched the excellent Julia Louis-Dreyfus movie You Hurt My Feelings. I snort-laughed through the entire film, which I saw at the local nonprofit theater where I volunteer (a wonderful way to make friends in a new city, FWIW!). It sparked all sorts of interesting conversations about relationships and communication, art and taste, career choices and existential crises—topics I’ve continued to mull over long after the movie ended.

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,

I’d like to hear your take on how to offer and request help during hard times, and how to go about giving people what they need.

Dear reader,

I’m so glad you asked. I’ve written about the power of interdependence, but in addition to persuading others of its importance, I’d love to provide something more actionable—a kind of “User’s Guide to Interdependence,” if you will.

Because let’s be real: it’s one thing to appreciate the beauty of assisting and relying on others. It’s quite another to navigate the many nuances of trying to help someone, and letting others help you!

Below, I’ll try my hand at drafting that guide.

Thoughts on offering help during hard times

In no particular order, here are just some of the approaches that have worked in my experience:

✅ Ask what you can contribute.

Your loved one might not have a good answer; they either don’t know what would improve their situation, or are too overwhelmed to pinpoint a specific request. That’s normal. But there’s a chance they’ll offer something concrete: “I need you to drop off dinner on Tuesday night.” Asking directly is your best chance of finding out exactly what’s needed.

✅ Decide what you can offer consistently, and just keep doing it.

My friend Wendy gave this tip when asked for her secret as a Support System All-Star: identify a sustainable action, commit to repeating it, and with time, your loved one will learn they can rely on you. When my mom was sick, a friend called her each week from the grocery store to ask if she needed staples like milk or bananas. It was simple enough to repeat regularly, but a huge source of relief for my mom.

✅ Do something you’re awesome at, or well-positioned to do.

A friend interested in healing work donated an at-home sound bath experience to my mom. My coworkers made my daily work-plus-caregiving juggle possible. One family friend (a fabulous writer) penned a beautiful letter as consolation when my mom passed. My mom’s neighbors—a handyman and real estate agent—moved mountains helping with the sale of her house. Something about your individual skills, interests, expertise, and position in someone’s life will enable you to be of unique service.

✅ Think of life’s biggest challenges as a relay race.

When my mom was sick, my family worked together as a relay team; you’ll probably need a team to help your loved one, too. Someone will run a lap, then get exhausted from the effort. While they recuperate, they’ll need to hand off the baton. And you’ll need to communicate with each other so the next transition goes smoothly, no matter who’s taking the lead at any given moment.

✅ Remember that no effort is too small.

Little gestures aren’t afterthoughts to their recipient. Thoughtful Instagram DMs and “thinking of you” texts always felt like warm hugs to me. If you’re weighing whether or not to send a short and sweet message, worried that it might not be “enough,” just do it. A few caring sentences will remind your loved one that they’re not alone.

✅ Make a grand gesture or step into a leadership vacuum, if you’re able and inclined.

Before my mom got sick, I didn’t know her cousins well. That changed when she went into hospice care. One of them realized that our family needed extra support, and became indispensable: when the biggest medical and emotional crisis occurred, she got on a plane without being asked. She made end-of-life arrangements when nobody else could bear to. She intuitively understood when to charge forward, and when to step back—both crucial aspects of leadership.

✅ Do something at a less-obvious moment.

One wonderful friend would—among other shows of support—send me a few bucks via PayPal when I flew from Seattle to Chicago to be with my mom, noting “Safe travels. Treat yourself to coffee at the airport on me!” It was touching to know that, as I was schlepping an overstuffed suitcase halfway across the country, someone was out there trying to make my day just a little bit better.

✅ Don’t spend too much time trying to triangulate the ideal way to be supportive.

Sometimes, during a challenging experience, your friend’s fridge will be barren; other times, it’ll be bursting with food from other well-meaning friends. Some people find bouquets to be a source of unadulterated joy; others think it’s a pain to find a vase when they’re busy with countless other problems. Bring dinner anyway. Buy flowers anyway. Finding the perfect way to help isn’t the point.

✅ Realize that you might say the wrong thing, and that’s okay.

As I navigated death, divorce, and a layoff, the people who always knew the right thing to do and say were—you guessed it!—people who’d been through the exact same things. That said, it was equally touching to hear from people who didn’t know what to do, but tried their best anyway. Someday, with enough life experience and practice, you might learn the “correct” way to show up. Until then, your genuine, sincere intent is enough.

✅ Consider this an opportunity to make a new connection.

When I was helping my mom, her friends—some of whom I’d never met—took extra time to establish a relationship with (and check in on) me, in addition to spending quality time with her. If there’s someone connected to your loved one that could also use support—a significant other, kid, or parent—consider reaching out to them, too.

✅ Give your loved one a break from their own tragedy.

You know them best: they might actually want some comic relief! They might want to hear about your struggles, even if they’re small in comparison. They might want to reminisce about good times, debate current events, or gossip about Harry and Meghan’s latest. Support doesn’t always look like focusing relentlessly on the hard stuff.

✅ Check in after the acute stage of the challenge.

Your loved one might receive a flood of help as a trying event unfolds, only to find themselves with Big Emotions—and not much support—later on. Check back in after you think it’s necessary; it might be exactly the right time.

Thoughts on requesting help during hard times

I’ll be honest, this is hard for me. So while I can’t pretend to be a pro, I have learned a few things that might be useful:

✅ Let people know what’s going on in your life.

This is Step 1; if your crew isn’t aware, it’s impossible for them to help you. I wasn’t open with many people about my separation because I felt like a failure when my marriage ended. Even though those closest to me were total rock stars, remaining quiet meant I didn’t get enough support around this particular challenge.

✅ If someone asks how you’re doing, don’t sugarcoat things.

Even when asked directly, many of us paint too-rosy pictures about how things are going. We might be motivated by pride or shame, or we simply don’t want to worry others. As above: this is not helpful! When you hide the fact that you’re hurting or struggling, you’ve denied your loved ones the chance to step up proactively.

✅ Remember that everyone has a different capacity for helping.

Some people in your life will have emotional blockages around hard things. Maybe talking about illness and death makes them terrified about their own vulnerability and mortality, or talking about marital struggles reminds them of their own relationship problems. That’s okay; they may be amazing at something else, like pitching in with logistics or errands. Others will be in the midst of grappling with their own crises—ones that you may not even know about. That’s okay, too—and it’s why we talk about having support networks. Relying on one person as the single point of failure isn’t fair to them, and it doesn’t serve you.

✅ Figure out what concrete help you need, and who’s in the best position to give it.

When you’re exhausted, emotionally devastated, or panicking, this feels almost impossible to do. Make time for it anyway. People genuinely want to help, but many aren’t sure how; by identifying a couple of small, tangible tasks, and matching them with the right person for the job, it’s easier to ask—and easier for your loved ones to say yes.

✅ Know that if you create systems, it’s easier to hand off part of that system to someone else.

I noticed that my mom and her (totally heroic) health aides kept experiencing grocery crises: the right supplies weren’t available in the right quantities at the right times, Instacart orders were minor fire drills, and everyone was just a little bit cranky about it. Creating a grocery system together—in which each part of the ordering process was assigned to a single person with a specific weekly deadline—meant that everyone knew their role, and stepped up to meet it.

✅ When you ask for help, hope for “yes,” but be okay with “no.”

This is a tough pill to swallow for anyone who has a hard time requesting help, but if you’re going to fall apart if you hear “no,” then your “request” is actually a demand. This is a reason to practice asking for help when you’re not desperate, so you can get more comfortable with direct communication before a crisis hits—and with the idea that relying on others isn’t a sign of weakness. It’ll make your future asks matter-of-fact, rather than (unwittingly) manipulative.

✅ If you hear “no,” remember the kind of long-term relationship you want with this person.

For some reason, your loved one can’t help in the way you’d prefer. It’s time to have a serious conversation with yourself: is this the hill you want to die on? Will this interaction be the beginning of the end of your close relationship? Maybe the answer is yes, if the stakes are high enough and this situation is indicative of a bigger imbalance or rift. But maybe you don’t want your future relationship to be affected. If that’s the case, respond carefully, especially if your feelings are hurt.

✅ Consider professional support.

As the saying goes: from each according to his budget, to each according to his needs. Depending on your disposable income, your comfort level in asking loved ones for help, and the intractability of the problem, you might hire help early in the process, or only as a last resort. Either way, remember that it’s always an option to pay people to complete discrete tasks for you, to hop onboard as caregivers, or to facilitate therapy sessions when you need extra support (or are stuck in an negative thought loop—been there!).

💬 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