Remotely Interesting

Work Style Profile: Steph Smith

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10 min read

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Welcome to the next profile in our Work Styles series! In each profile, we highlight one person's untraditional workday. You'll get an inside look at alternatives to the traditional 9-5, Monday-Friday schedule (and maybe pick up something new to try).

Today, we're featuring the amazing Steph Smith! Steph is the Director of Marketing at HubSpot and juggles multiple endeavors on the side, including her podcast, book, and blog. She's been working remotely for 5+ years and is an experienced digital nomad who has explored 50+ countries.

In this profile, we get an inside look at her approach to juggling multiple roles, how she went from finding remote work freedom confusing to embracing the potential, and how she's even more productive since saying goodbye to the traditional 9-5 workday. Let's dive in!

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Steph Smith on a beach with penguins

What does a day in your work life look like?

"Honestly, every single day looks different. Some days I wake up at 7AM and others I wake up at 10AM. Some days are filled with calls (hopefully not too often), while others I’ve completely time blocked. Some days are spent strategizing, while others are spent heads down getting sh** done.

This has to do with my job being pretty broad (leading a digital product), my varied interests and projects, and the fact that I’ve never been much of a regimented person -- even in university, I struggled to go to lectures because they didn’t adhere to when and how I learned best.

Although each day looks different, my weeks have some elements of consistency, including what I consider to be a few 80/20 things that have made my days better. The full list is covered in my course, Doing Time Right, which covers my entire productivity philosophy: Eliminate, Automate, Delegate, Iterate.

  1. Front-loading: Early on in my time working remotely, I realized that not every day needed to look the same. I also noticed that I would get unnecessarily stressed near the end of the week because I didn’t get everything that I wanted to be done. Over time, I found that working really hard on Mondays and then slowly easing up by Friday worked really well for me. For example, I prefer a 12, 12, 8, 6 2 spread of my week, compared to 8, 8, 8, 8, 8.
  2. Parkinson’s Law: Related to the idea of front-loading, I prefer to work like a lion, instead of a cow. In clearer terms, I prefer to sprint when I’m 'on' and relax when I’m 'off'. Especially with my personal projects, this manifests in setting ambitious (even if arbitrary) deadlines that I sprint towards and then recharge for months in between. I did this with both my book and my course, which were completed in 7 weeks and 3 weeks respectively.
  3. Meeting-free days: I try to ensure at least one full meeting-free day. As of late, this has been Wednesdays, so it gives me time to catch up on 'hump day' before the end of the week.
  4. Time blocking: Speaking of meeting-free days, I utilize weekly time blocking at the beginning of each week to make sure that I make progress across a few important items. Without these blocks, I’ve noticed that time will fly and I’ll have been 'busy', but not productive.
  5. Get outside: For a long-time, especially during peak pandemic, I forgot how important exercise and sunlight were. It sounds silly, but I know I’m not the only one. Lately, I’ve made sure that I get outside and move daily. I’ve found listening to the Huberman lab podcast a huge motivator in focusing on these parts of my life."

What approach did you take to optimize your work schedule for you?

"Even though I had only worked a 'desk job' for a year prior, the first few months of working completely remotely were surprisingly difficult.

I distinctly remember feeling this sense of confusion.

Was this a real job? Do I really not have to tell my boss about my dentist appointment at 2pm on Wednesday? Is he really okay with me moving to Europe or is he just saying that?

I was so used to having everything pre-defined for me that freedom was confusing. My slate was wiped clean, turning my schedule from something with rigid expectations, instructions, and hours to something considerably more ambiguous.

It took me a while to really get my head around all of this since every experience prior had taught me that this was not the way the world worked. To put it bluntly, I had never been given this level of trust and autonomy, and at first, I wasn’t prepared for it.

In particular, there was no one to set boundaries for me and it took me somewhere between 6-12 months to really design a work environment that was optimal. In other words, it really was a job to learn to become more effective, which meant isolating how to elevate my strengths and limit my weaknesses. Some people end up opting out of that pursuit and prefer to be told how to work. Although it’s an upfront investment, it has paid dividends for years to come.

The results of this testing include the examples in my prior answer. But in order to get to those answers, I needed to collect information.

This information ranged from what times of day I was most productive to whether I preferred to work from a cafe or from my bed. It also included tracking: something I started to take more seriously in 2018 when I learned to code. I sometimes refer to that year as my 'year of sponge', because that’s when I got serious about tracking daily progress towards my goals.

This was a fundamental shift for me because KPIs no longer were just for work -- they were for my personal life too.

Through that data, I was able to get an accurate reflection of how I worked, instead of just a perception through hindsight. Some people have an adverse reaction to this level of tracking, but I think that during the early stages of remote work, it gave me the feedback mechanisms I needed.

Finally, this attention towards how I was spending my time uncovered a clear distinction between 'busyness' and 'productivity' which I label as meta and absolute tasks, which I describe below through an excerpt from an article of mine. As I continue to evolve my schedule, I’m constantly asking the question, 'How can I make room for more absolute tasks?'

My definition of meta work is the following: 'If you did that activity continuously for a year, would your life be any different?'
If I answered emails every day for the next year, would my life have changed in any significant way? In other words, would I have moved from A to B? The answer is no.
The same thing is true for things like laundry or buying groceries or doing your nails. Oh yes, Netflix fits neatly in there too.
There’s a second type of task which I label as absolute tasks. If done consistently, you would likely see your skillset or life change in a material way.
For example: if you read every day for a year, your knowledge set, creativity, and reading speed would all likely improve. If you exercised every day, your health would undoubtedly improve. Similarly, if you dedicated 1 hour every day to learn to code, you would have an entirely new skillset by the end of the year.
While meta tasks are unavoidable in life, make sure that your goals in life are not meta — they need to be absolute. When you create your to-do list for the day, make sure at least one thing is absolute (remember: 1.01³⁶⁵ = 37.8). And of course, when you can: automate as many of the meta tasks as you can. Meta tasks in many ways can be synonymous with distractions unless they bring some sort of independent joy to your life."

Why did you choose to go against the standard 9-5 schedule?

"I’d like to flip this question on its head and encourage people to ask the question, 'Why do I feel the need to work the standard 9-5 schedule?'

I worked the standard 9-5 for around a year, commuting ~2 hours round trip daily. Throughout that entire period, I couldn’t understand why work needed to operate that way, because just as I do today, 99% of my work was done through the Internet.

The more I peeled back the layers, the more I realized that it was more tradition than optimization.

It’s pretty crazy when you stop to think about it:

twitter profile avatar
Steph Smith
Twitter Logo
September 3rd 2021

When I realized that the 40HWW was mostly a remnant of the past, it was pretty easy for me to choose an alternative. And since then, it’s been clear that I will never return.

There are so many traditions that exist all around us. Many of them exist for a reason, but in their passing from generation to generation, people forget to question them and whether their original impetus still makes sense.

Whether it’s the 40HWW, 3 meals a day, or marriage -- I would encourage people to learn about the traditions that they’ve so readily accepted, not because they’re terrible things, but so that they can understand whether it’s still applicable today or whether they can create something better."

What's one area you're still looking to improve?

"Saying no. I’ve found that learning to say no is a life-long lesson that forever keeps kicking me in the butt.

And its relevance grows the more control you have over your time; increased freedom simultaneously allows you to do more, but can also enable you to stretch yourself too thin.

It’s taken time for me to internalize that time is truly zero sum and that I need to start treating it as such. That means that I can’t continue to do all of the things that are 'nice to have', but instead need to focus on the few things that are essential.

I started from a place of little opportunity and a lot of time. Over time, that inverted, and I have much less time than opportunities available, but I have needed to retrain my brain to operate this way."

What is your top tip for someone wanting to transition away from the standard work schedule?

"Remote work (or similarly, autonomy or a flexible schedule) is not an 'end goal'.

Many people see the glamorized version of remote work and hope that it will solve their problems. But remote work is just an enabler… just an extension of normal work. It gives you more autonomy to design your life, but that still means that you need to actively do that. And it certainly will not bring you happiness on its own. You still need to invest in your skills, relationships, and goals because they will not develop without effort. Just like any challenge, you’ll be rewarded accordingly.

If you choose to work flexibly, expect challenges and roadblocks because they’re a part of life, remote or otherwise. And as you embark on this journey, remember not to sacrifice your integrity or personal goals. For example, don’t take a remote job that you hate, just because it’s more flexible. You still have to spend ~⅓ of your life there!

One universal downside of remote work is the social aspect that it can bring (or not bring).

Offices allow coworkers to experience hundreds of micro-interactions each day. Remote communication tends to be more transactional and therefore requires even more investment.

If relationships are built off of quality time, the answer is not necessarily more calls -- it’s more genuine interaction -- quality time. Interaction could be an office gym challenge. It could be a weekly hangout with no business talk. It could be quarterly retreats.

What I see so many companies do is treat every call the same: the first fraction allocated to 'small talk' and the rest to 'business'. Instead of diluting every call, set aside specific time for bonding. For example, instead of having 20 hours of mediocre calls through the week, most companies could reduce that to 5 hours (or less) of highly productive calls and 1-2 hours of calls dedicated to bonding, which from my experience, is a better formula for relationship building.

I will end this segment by bringing back the idea of narratives. We’ve grown to think that our coworkers should be some of our closest friends and there is absolutely nothing wrong with that. But it’s also important to remember that with a new way of work, you can have healthy work relationships and even healthier relationships with people physically around you. This is partially why pandemic remote work was so difficult -- you didn’t have the physical outlets for connection available."

Final thoughts?

"Remote work is whatever you want it to be. It wipes your slate clean, allowing you to build your own approach to work. In the same way that we don’t need to work 9-5 M-F, you don’t need to get up and travel the world, just because you may now have access to it.

In other words, having autonomy is not about having no rules, but ridding yourself of the rules forced upon you and developing your own set. Sometimes those rules end up quite similar to where you started. Sometimes they’re entirely new."

Big thank you to Steph Smith for giving us an inside look at her workday schedule!

Highly recommend checking out her podcast, the Shit You Don't Learn in School, if you're interested in learning more about remote work and getting more out of life (especially this episode on narratives: Does Marriage, Retirement, or the 40-Hour Work Week Still Make Sense?).

If you're interested in maximizing your time, check out her course, Doing Time Right. Also, follow her on Twitter or her blog, where she frequently writes about remote work.

I'd love to hear from you! What did you find interesting about Steph's workday? What could you potentially try out yourself?

Feel free to reply to this message or DM me on Twitter @mar15sa.

I truly appreciate you taking the time to read this. Hope you have a lovely day!


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