From Collecting Trophies to Capturing Time + 🎉Roundy Roundup🙌

Words of wisdom from a Roundy Award recipient on how being a marketing exec isn't the be-all and end-all.

Jun 13, 2023

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The Roundy Award has launched!

This award celebrates well-rounded lives, beyond the career hustle.

I recently wrote about how our most prestigious awards encourage narrowly focused lives. More so, that public recognition for self-care and care for others shows up only in obituaries.

So, I created The Roundy Award to showcase people who fill their life with meaningful work, self-care and care for others.

With all the confetti and high-fives, I’m excited to share two things here:

The first 27 Roundy Award recipients!!
Sean’s Roundy Story that shares how he gave up collecting professional trophies and prioritizes time instead

🙌🎊 The Inaugural Roundy Award Recipients 🙌🎊

Mike, Canada
Amanda, Canada
Gui, Canada
Alia, Canada
Valerie, Canada
Ben, Canada
Nitya, United States
Amanda, Canada
Rahul, Canada
Bosky, Canada
Sharon, Ireland
Sonia, India
Aalia, Canada
Rebecca, Australia
Peggy, Canada
Elia, Germany
Brandon, Canada
Sean, Canada
Kata, Spain
Hailey, Canada
Tyler, Canada
Brian, Canada
Sonam, Canada
Ashley, Canada
Porter, United States
Madison, Canada
Julia, Canada

Kudos to you all for following your own personal path and creating a life full of work, self-care and care for others. We see you and appreciate you. 🫶

Know someone that deserves a Roundy Award for their well-rounded life? Recognize them for all they do.

Nominate for a Roundy Award

Sean’s Roundy Story

In a world all about money and success, Sean's story reminds us: time is what truly counts.

He went from chasing trophies and burning out to cherishing time with loved ones. It's a common tale, often overshadowed by flashy success stories.

So to counteract the hustle hype, here's Sean's story. In our interview, he shares how he found stability and fulfillment through fractional work, while admitting he's still working on getting enough sleep (because hey, no one's perfect!).

Note: Our discussion is slightly redacted and edited because, like, you don’t want to read, like, how we… um… actually talk - oh look a butterfly! - when we were in a free flowing conversation.

What is important to you in life?

Time.

Time is the most important thing in my life. It became clear to me in the last couple of years. Throughout my career in the tech startup world, I worked excessively, around 60 to 100 hours per week, constantly burning out. I believed that working more would lead to progress, more money, better titles. I was accumulating shiny trophies.

However, I neglected my relationships with family and friends. I didn't give them enough time and attention. When I evaluated my happiness and the effectiveness of my time, I realized that despite making a lot of money and achieving career success, I wasn't satisfied.

Now, I'm focusing on working less and optimizing my time. I've set boundaries, like not working on Fridays. That is my day for myself to bike, to do longer trips, to go see family, whatever it is.

I feel like a better person in my loved one's lives. I actually feel more present now. Previously, people would say “oh that’s Sean. He’s always busy”. They perceived me as successful and without any time for them. But I now realize that isn't as important to me. I’m glad I’m not continuing down that path.

Now that you prioritize time, how is life different for you? What have you figured out that others are still struggling with?

For me, fractional work has been the answer to getting more time.

I get asked a lot how to move away from full-time work. They want to pursue something akin to what I'm doing with fractional CMO kind of work and I genuinely believe it's achievable.

For example, I position myself as a fractional CMO, enabling me to maintain a good income because now I know my hours, I know the highest impact things to do with my time.

A lot of time is spent on low-impact tasks. This is the reality for many individuals. I often ask people, especially in marketing, to evaluate their calendars and consider how easily they can connect their last hour's work to its impact on the business. If the connection isn't clear, chances are it's not the highest-impact task.

I realized that I spent a substantial amount of time on tasks that weren't effective. Now that I do contract work as a fractional CMO, I can use my time for high impact work and then all the other things like biking (with Georgia!), traveling and being with my loved ones.

This transition to four days a week, fractional work sounds blissful. What’s been hard about it?

When deciding to work four days a week I also decided to only take on two clients at a time. That meant I was going to earn less and the hardest part for me was reminding myself that I am still skilled at what I do.

This realization has been particularly challenging in the past six months. Honestly, I'm earning significantly less this year. I questioned whether I was still good at my job and if I was worthy. Why wasn't I trying to make more money when that's what I had always done?

My entire professional life was focused on increasing my salary. Now, intentionally taking on fewer clients and engaging in unpaid activities, along with adopting a nomadic lifestyle, has brought more balance into my life. However, I worry about becoming out of touch.

I genuinely love working, especially in areas that bring me intrinsic value, like coaching, problem-solving, and data literacy. The internal struggle is real. Is it okay to work only two days a week while still covering my financial needs, leaving three days for other pursuits? Am I being lazy? Will I forget my professional skills? Will people take me seriously if I don't work crazy hours?

It's difficult to transition from a mindset of startup growth at any cost, backed by venture capital, constantly building and laying off teams. Stepping away, I've come to realize that the system is somewhat rigged. I've learned how to make money while working fewer hours.

Now I have a lifestyle where I can be nomadic, spend three days cycling, and not be constantly tied up in calls. The calls I do have are high-impact, where an hour of my time can save someone half a million dollars. So why do I feel the need to justify working the remaining 39 hours of the week? I don't. But, intentionally making less money so I have more time for other things is a challenging mindset to maintain.

So basically every professional should switch to fractional work?

No, no, I don't think everybody should quit their full-time job. I think that people could have a better relationships with their work. They can say to their manager, “Hey, this is what you need from the role. I can do that in three days a week. If you don't get what you need, we'll revisit. But I don't need to work five days a week to do this.”

And I think that's key. Valuing time makes work more about the outcomes, less about the inputs.

Your self-worth isn't correlated to how much money you make. How has that unlocked a new way of living?

I think that we've built our careers to make our family, parents and partner happy. It was a big celebration if I got a raise, a promotion, or a new job. For me, those things don't really matter anymore.

Another good example of this is a product designer who I’ve known for a while. She was ten years into her career and asked me about going fractional. She and her husband wanted to be in the woods more. So she packaged up her experience, figured out what to charge from a billing standpoint and she's been doing it for a year now. Now, when I try ping her on a Thursday or Friday I get her out of office response saying “I'm in the woods. I'll talk to you next week”. She has the balance that she's looking for and loves it.

This story and for me having the time to do the things that fill my day is so much more meaningful than any other big number that I've posted on a board.

Switching topics, where are you imperfect? What have you let drop?

It's only recently that I started taking my sleep more seriously. For a significant portion of my adult life, I struggled with sleep due to past trauma from my college years and I let it get the best of me and it really messed up my sleep.

To make it worse, once I started working and couldn’t sleep, I would think to myself "Why waste this time lying in bed? I should start consulting and doing side gigs to make more money since I'm awake anyway." This mindset was a major mistake and had a detrimental impact on my physical health.

Now, I'm focused on building a sleep routine. I used to rely on melatonin, but it stopped being effective. I even went to a sleep clinic, and they told me that my problem was an inability to quiet my mind. I would lie in bed worrying and replaying my entire day.

So now, my goal is to let go of things more quickly. I tend to hold onto things for too long, and they affect me excessively. I struggle with anxiety related to these matters.

I've come to realize, especially as I approach 40, that I need to prioritize my health. Sleep is something I'm trying to take more seriously now. However, the difficult part is that if I sleep in, I immediately feel guilty, as if I've wasted my morning. There are people in my life who encourage me to sleep more, emphasizing that I deserve it and should enjoy it. Yet, when I wake up, I find myself thinking about what I could have done differently during that time. I feel like I should have gotten up, responded to messages, sent emails, or addressed feedback on presentations that someone has been waiting for.

I'm striving to set myself up for success by not booking early morning commitments and avoiding staying out too late. Sleep is an area where I'm actively working on improvement. I'm not where I should be yet, but I recognize the need to get better.

Instead of wealth or power, what value would you elevate on a pedestal for society?

I come back to the first question: time. I just don't know why we don't optimize more for time. With time you have more optionality in life. More money doesn't mean more optionality really. It means you can buy things and you have a bit more padding. But with time, I get to go hang out with my parents whenever I want. I get to go for walks. I get to do whatever I want.

Time is probably the most freeing currency that you can have. And it's the thing that we don't know how much we have, we undervalue it constantly and we're always running out of it.

I wish people understood how important time is right now. The thing that has been the biggest eye-opener for me is that we build our entire lives to retire at 60 or 65, and then we try to enjoy ourselves. Why? Why are we waiting so long to do that?

I get there's the pressures of financials we have all these things we've gotta work on, but I think there's an Option C here where we can figure out how to make the money we need to make, and actually enjoy ourselves when we're healthy and our parents are around, or our loved ones, or the people that we've built as our family.

I think the best thing I have done for myself is I have built a significantly bigger bank of time. My time is the thing I point to as my success.

All I'm doing now is trying to spend time with my parents - whether they enjoy it or they're like, “Sean, give us some space!”. I want to know that I made as much effort as possible while they're still alive. That's the part I get emotional about.

So there you have it folks, our first of many Roundy Stories to come!

Sean’s story shows me that a well-rounded life is not something to be achieved but rather something to be maintained.

A well-rounded life requires self-reflection of what’s important and constant improvement and shifting as life ebbs and flows. And that’s just as hard as a singular focus on professional success.

Sean’s definitely deserving of his Roundy Award (even if he did stop chasing trophies 🏆😉).

Till next time keep well,

🐶

P.S. I’m prioritizing shipping over perfection, so this post may not convey all my thoughts perfectly. I’d love comments or questions to keep the discovery going.