Most people use to-do lists to plan their days. To-do lists are great for prioritizing, tracking progress, and, most importantly – not missing out on something important.
Despite that, almost all of us miss out on including an insanely important task in our to-do lists. This task is called “leveling up.”
I was as ignorant of “leveling up” as anyone else until I heard it from Daniel Scrivner, the CEO of Flow. According to Daniel, putting a “level up!” task box on his daily to-do list reminds him to do something out of his comfort zone, something that’ll push him to go beyond his normal limits.
The next logical question is, when do you check this box? What do you actually need to do to say, “I leveled up today”?
Here’s what Daniel has to say on that, “I can only check that box if I feel I have gone above and beyond myself and done something great. For example, I tick off that box when I have a difficult conversation despite not wanting to do it as it's so hard. Other examples are days when I do something special for my wife or finding time to work out on a hectic day.
“Yesterday evening, I was thinking, ‘I'm not going to check off that box today.’ Then I went home and figured something out that I was grappling with for a couple of days. Then I was like, ‘yes, I did it!’. It’s always an incredible feeling to check off that box.”
This idea is brilliant because we are so closely attached to our to-do lists that anything that’s not on the list doesn’t get our attention. “Leveling up” ourselves is something we can’t afford to ignore, and there’s no better way of giving it more attention than by putting it on our daily to-do list.
So the next time you are making your to-do list, make sure to include a “level up!” box in your list.
In our entire conversation, Daniel talks about his experience at leading Flow, observing bubbles in our heads, using paper as the operating system of life, when and how to say ‘no,’ why it’s important to have difficult conversations, protecting the mornings for output and writing self-addressed memos.
You won’t stop getting amazed by Daniel’s ideas throughout the conversation; that’s a promise. Let’s dive straight in!
Daniel introduces himself
Hi, I’m Daniel Scrivner, the CEO of Flow and host of the Outliers podcast. I also manage BlackLetter, the venture through which I've done 100+ of my investments. I joined Flow two years ago, and it was my first stint in an operations role. My background is predominantly design-heavy. I have led many design teams at various companies and always wanted to see what it's like leading at companies. Flow felt like an opportunity to take my design and product experience to a very designed-centric tool. At this point, Flow takes up most of my time.
I have a variety of interests like investing, so I invest in early-stage and venture-backed companies. I also do a lot of advising work with different companies and venture capital funds. It may sound like a lot of stuff, but for me, all those things feed into one another. What I learn as an operator helps me become a better investor, what I understand by advising companies helps me become a better operator, so on.
Journey at Flow
The journey at Flow has been intense. Flow will be turning ten this year. I joined when the company was eight years old. The goal was to turn the business around. We were operating in a highly competitive market. I learned a lot about the business from the team that was already there, tried to refine what we offer and what differentiates us from competitors. Then in about 1.5 years of my joining, we launched a redesigned product called FlowX last year, and it's gone really well. Since then, we’re never done. We’re always trying to make it better.
Balancing between design & operations
It’s definitely challenging to balance my design interest with my operations role at Flow, but I’d say I have gotten better at that over time. I use my experience working at companies like Apple, Square, Disney, Nike to do good at operations.
I don’t indulge in design a lot now, although I’d love to do that. But having a massive design experience helps. Like at Flow, we’ve updated the company’s branding over the past couple of years, and I would be significantly handicapped if I had not done that for multiple companies multiple times in the past.
Besides that, I feel the design is a significant competitive advantage in the present business world.
Earn the right to take risks
I’ve learned in investing and business that you’ve to earn the right to take risks. What that means is, telling yourself that this isn’t supposed to be easy; you’ve to go and do the work.
If you do the work and build a solid foundation, then you get the right to take risks and have fun. You get the chance to spend the money, do advertising, write big cheques. But first you’ve to do the hard work to get that solid foundation in place on which you can build upon.
A typical day in the life of Daniel
At this point, we've got a 3-month-old. We're getting pretty good sleep – around 6-6.5 hours of sleep. At 5 AM, I hang out with my kid. Then I head out for the office by 8 or 8:30, and I'm in the office by around 9.
For the people who don't have kids, you're in an incredibly privileged position. You have 100% control over your time.
I plan my day on paper. I'll list all my meetings for the day and what are the absolutely important things on a piece of paper. Then I have a list of sprints. Sprints are a bucket of errands that I need to get done but aren’t very important. I put them all on a list and try to get them all done in one go within a set time frame. I call them sprints because I try to get through these as fast as possible. I literally put a clock in place to ensure that I complete them within the allotted time.
No two days of my days are alike, but my days always have some meetings, some deep work, and some work that's not deep but needs to get done. I do the “not-deep-but-needs-to-get-done” work in sprints.
I just make sure to have a good sense of my priorities, else it's very easy to go off-track. After finishing my day at work, I go home by around 5 PM and have dinner with family. We typically have dinner together with the family around 6 PM.
We put our kid to bed at around 7:30, and beyond that is what I call “my time.”
Observe the bubbles in your head
I’ve seen successful and curious people in general love taking on many things, but what comes along with those things is stress and anxiety. The way I’ve found to deal with that stress and anxiety is by observing the things that bubble up in my head and noting them down on my piece of paper.
After noting it down on paper, I ask myself, “why am I worried about this?”. It helps get a fair sense of the problem to deal with them the next day in office.
Once it’s down on paper, I essentially free up my mind from it to come back to it later and resolve it. If you’re working on many things, it’s normal for these bubbles to keep popping in your head, just write them down and deal with them later. That’s at least what I do.
When to say “no”?
It is one of those life meta-skills that you are never done mastering; there’s always scope for improvement. I do say ‘no’ quite often, especially in investing; if you’re not saying ‘no’ a lot, it means you’re investing in lower-quality companies.
So, how I go about making these decisions is by sitting and thinking where I’m headed and where I want to be in 2-3 months. Then I take it downstream, what I'll do in this quarter, in this month, in this week, and finally on this day to be on track to get there.
Even if it’s something really exciting comes up but it doesn’t align with where I want to go, it’ll be a ‘no’ from my side.
When to exit from a commitment?
The world is way more complex than we think it is. You can have perfect plans, and it might still not work out. The question then becomes when do you push through and when do you decide to draw a line in the sand. That is really really difficult.
For example, I run the Outliers podcast, and it's a lot of work. It isn't as easy as I'd like it to be, or anyone on the outside would think it is. But if you ask me if I'd stop doing that because of these reasons. The answer is no. I'd keep pushing through. The reason is as long as I enjoy doing it, I don't mind how much work it is.
The same thing with my investing. I just enjoy the process so much that I just keep pushing through on that. It is brutally difficult; there are very frustrating processes involved. But since I enjoy the process, I'd keep pushing through all that hard stuff.
These are always hard decisions whether to keep going with something or stop working on it, but if you look at it from your personal values perspective and what you enjoy doing, you'll be better positioned to make these decisions.
How to say ‘no’?
There's this quote that goes, "Easy decisions, hard life. Hard decisions, easy life."
It applies a lot here. Like I was advising a company, and two weeks in, it just didn't feel like a good fit. The first thing is you need to know what's the right thing to do. In my case, it was communicating that there wasn't a fitment. Next is to figure out how to communicate that in the most humane, warm way possible.
People often take the lowest energy way of opting out. What ends up happening is you burn that bridge in that relationship.
You have to make difficult decisions in life, and if you put yourself on the line by telephoning the other person or seeing them face to face, it’s insanely difficult, but I've never regretted doing that. When you do that, you acknowledge the other person. You give them empathy. You give them grace and treat them like a human.
You have to make difficult decisions in life, and if you put yourself on the line by telephoning the other person or seeing them face to face, it’s insanely difficult, but I've never regretted doing that.
The golden rule is highly applicable in this case. Whenever you're having a hard time figuring out what you should do, try to get in the other person's shoes and think about the way that I would want to be treated. With that, you'll make a better decision on dealing with such difficult situations and doing the right thing.
A daily task called "level up"
I've some daily habits that I make sure to do every day, like meditating, taking a walk, and some more health-related habits. But I've added this one box on my list every day called "level up," and I can only check that box if I feel I have gone above and beyond myself and done something great. For example, I tick off that box when I have a difficult conversation despite not wanting to do it as it's so hard.
Other examples are days when I do something special for my wife or finding time to work out on a really hectic day.
Keeping that box on my daily to-do list also gets in that gamification and competitiveness aspect into my days.
Favorite (and unusual) productivity tool
I just use paper for everything. Paper is like the operating system for my day. I do that for a couple of reasons. One thing that's been amazing over time is knowing when to close my computer. I think something that all of us struggle with is getting sucked into screens all day long, especially after Covid. We rarely get any time for reflection.
If everything you're going to do is on screens, you're never going to close your screen. So I start my day off in a calm place where all my screens are off, and I've some focus music playing (I use Endel for that). Then once I'm in the zone, I engage with that piece of paper for the day, and I keep going back to that paper throughout the day to ensure I'm on track and note down anything else that's bubbling in my head.
At the beginning of the day, I paint a picture of what the day should ideally look like. Besides, I let myself be flexible on when to pick what task on my to-do list. I can work on the 1st task and go directly to the 10th based on what I'm most excited to pick up on at that moment. That's just a great hack, especially if you have a lot of stuff to do.
We use Flow to work together as a team. So anything that's a team task goes there. All our product work is planned on Flow; it doesn't happen on my piece of paper. Later, I summarize all that's on Flow to my piece of paper, so I have a single source of truth.
Flow is excellent for anything that's team-related as all the details are there, all team conversations are there, you can see what the week looks like, you can see what the project work looks like. Then, I use many other tools, but the most important tool has to be paper and pencil.
Twitter is not a waste of time
I love Twitter. I follow a bunch of investors, entrepreneurs, and people that I feel are doing exciting things. People might look at it and say it's a total waste of time. In my view it's never a waste of time because I find new ideas, companies I should know more about, and interesting articles/books to read.
I timebox my time on Twitter. It's important to have constraints; else, it's hard to stop spending time there.
Protecting the mornings for output
I have my meetings in the afternoon. I'm generally more focused and sharp in the mornings, so I want to use that time to create output. In my view, meetings are more about inputs than outputs. That's why I let the morning be for deep work, and I start my meetings only in the afternoon.
Writing memos to self
If you told my 2-year past self that I'd be writing memos from myself, that person would think I've really gone off the deep end and taken this CEO thing too seriously. But the thing is, if you want to think about things deeply, you need to put away all the distractions and then try to organize your thoughts and emotions around a certain idea. I think the best way to do that is by writing.
Mohit's experience using pen and paper
Hi, this is Mohit, host of the Mailman podcast. I tried out Daniel’s idea of using pen and paper to organize my day and put my thoughts there. Here’s how it turned out for me.
It started with difficulty. Mostly because I don’t think linearly. I think in random points, scattered all across the place. Two days in, I realized, I do not have to use paper to make a linear list of things; the paper is all blank and wide, I can go nuts with it. And I went nuts!
My notes started looking something like this –
...and that’s when I realized the power of doing my thinking and planning on a paper instead of an app. I think I will continue doing my planning and thinking on a piece of paper more than on a screen. But I often wonder, how would I keep records of all these papers for historical reasons? That’s something I’m yet to figure out.
Back to our conversation with Daniel now.
One extra hour
If I had one extra hour, I'd just think and/or read. It works for me right now by trying to carve out that time, which is challenging at this point as we have a 3-month-old, and a 3-year-old at home, besides an intense job.
What I try to do is, for the last 2-3 hours before I go to bed every day, I indulge in whatever I'm most interested in. I’d quote Naval Ravikant here, “stay interested and stay engaged.” Which means there should be no compulsion in learning. Don’t push through a book because you’ve to complete it; read it because you find it interesting.
Don't guilt-trip yourself to be interested in something. Allow yourself the grace to be obsessed about anything. I've got books about a wide variety of topics. For me, everything in the world is connected. Everything that I've read has helped me become a better manager or in some other way. So I’d spend that extra hour exploring my curiosity and reading more.
How to get in touch with Daniel?
I tweet on and off, but people can find me on Twitter at @danielscrivner. You can also visit danielscrivner.com; that’s where you can find all the interviews that I do for the Outliers podcast. We release a new episode every week on Tuesdays, or you can also visit outliers.fm.