“Someday” is a dangerous word

At the beginning of the movie Knight and Day (a fun and mindless favorite of mine), Cameron Diaz’s character is chatting with Tom Cruise’s character, describing her plans to finish restoring her deceased father’s ‘66 GTO and give it to her sister as a wedding present. Then, she shares this:

“I used to think that, someday, when the last part went in, I would just climb into that GTO and start it up. Just drive and drive and drive, and just keep driving until I got to the tip of South America.”

“Yeah, ‘someday,’ Tom replies. “That’s a dangerous word. It’s really just code for ‘never.’”

This line often pops into my head when I hear people talk about their “someday” dreams and goals. And it’s not because I’m cynical — it’s because I’m realistic. 

I’m a big believer in acknowledging my finite existence and the reality that I won’t get to do all of the things I want to do before I die. I’ve even gone so far as to advocate for “anti-bucket” lists as a way to eliminate dreams and goals you don’t want to prioritize. 

However.

For the few things that you really, desperately want to do “someday,” I recommend making them happen as soon as possible.

If you mentally file your goals and dreams in a folder marked “after retirement,” there’s no guarantee you’ll ever be able to do them. Life may bring life-changing illness or injury to you or someone close to you. Or you may die young. 

There is also a huge, hidden benefit of having big, bucket-list experiences earlier in your life. In his book Die With Zero, writer and businessman Bill Perkins calls it “memory dividends” — an eyeroll-inducing bit of jargon that I actually sort of love.

Memory dividends are essentially the ROI we receive from creating memories. In the same way that early and consistent contributions to a 401k will (hopefully) grow to support us in retirement, early and consistent memory-making grows into a lifetime of joy to remember and reflect on.

To be honest, how you proceed with prioritizing your goals depends heavily on your list. If “raise a family” is one of your big dreams, you might shelve “go skydiving” for the foreseeable future. If “visit all 50 states in an RV” is on your list, you might need to save up for a sabbatical or find a flexible, remote job. 

The point is that your biggest goals deserve thoughtful consideration and planning right now, not in 20 or 30 years.

My husband had a bucket list experience this week: riding in a hot air balloon. He’s been thinking about it for a few years, but it escalated into a sort of hyperfixation this spring. 

So he just… booked a flight. 

(Since I know people will ask: I opted to document the experience from the ground this time, but I would consider joining in the future. 😂)

This morning, he received an email from the balloon company with his “Certificate of Ascension” (I love that). He already wants to ascend again. He’s even talking about training to become a balloon pilot 🫣

Not all dreams come true for as little as $300 and a few hours, but some require even less. 

My own bucket list, which lives in my Notes app, lists 60+ experiences and goals. Some are expensive (Pay off student loans, Design and build a custom home) and some are not (Paint a mural, Officiate a wedding). Some are already checked off! (Visit Ireland, See the Northern Lights, Sew a dress.)

I’m going to spend some time on my list, deciding which goals are closest to my heart and the next steps to take toward them.

Are you?

If you need some inspiration, here are a few common bucket list items. Pick your favorite!

See you next week,

Kara

Out of Office

What I’m doing when I’m not working

• While Dawson was up in the hot air balloon, I hopped in the chase vehicle with the crew! We followed the balloon through Saskatoon and picked it up after it landed in a hay field.

• I recently finished a really good book: The Correspondent by Virginia Evans. It’s a novel in letters, and the audiobook featured a full cast. The performances were stunning, and the story was really moving and lovely. What are you reading?

• I watched Happy Gilmore for the first time because everyone’s been talking about the sequel. I can see why it’s beloved, but I think once is enough for me. ⛳

P.S. Got a question about self-employment, anti-hustle culture, business books, or something else?

Kara Detwiller is a writer and creative based in small-town Saskatchewan. She specializes in long-form content writing for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. To connect, reply to this email or find Kara on LinkedIn. To support her work on Wishful Working, share this email with someone or buy her a “coffee.”

Why Wishful Working? I write this newsletter because I want to see more people enjoy a life not centered around work. For some, the path to freedom and flexibility is through self-employment, but we also need to challenge cultural norms and champion healthier working conditions and work/life balance for all types of workers.