For a while now I’ve been chipping away at a photo hosting and photo sharing product that I’ve dubbed Shoebox. 
It started as an experiment, and it’s become an ongoing, iterative journey in to what a lightweight photo sharing service can be. But why even start? Do we really need another place to store our photos? Why Shoebox?
For a while now I’ve been chipping away at a photo hosting and photo sharing product that I’ve dubbed Shoebox. It started as an experiment, and it’s become an ongoing, iterative journey in to what a lightweight photo sharing service can be. But why even start? Do we really need another place to store our photos? Why Shoebox?
At the time of writing this, I have about 18 years worth of photos to look back on. In the past two decades we have gone from the first digital SLRs to small mirrorless cameras with amazing low-light and video performance, and at the same time, we have seen the rise of a completely new class of camera — phone cameras — with impressive computational performance. 
And as cameras have gotten better, smaller, and more ever-present, the volume of photos we take per year has dramatically increased. Most of us shoot more photos on their phone in a month than they do on a dedicated camera in year.
The sheer volume of photographs brings with it some very interesting problems. There are commodity problems — like storage and backups/recovery. There are communication problems — where images have become a primary way of communicating. But the thing that I am really interested in is the value that lives inside of these images. 
While we relegate them down to bits and bytes stored on devices and in clouds, their meaning is much more than that; many of these images are triggers for our mind. At minimum, they are a picture of us smiling in front of a point of interest, that open up our memories of a trip we took. Often, they are a set of photos that remind you of who was there with you, who you were back then, and why you were there. These photographs are a rich source of memories and emotions. 
Most of these memories are private ones, and we have plenty of ways to share them with our friends — mostly through different messaging services. There are even some dedicated products for this, like Cocoon.
However, in many cases, these images and these memories can also convey stories; ones that we want to make available to the public realm. And in today’s environment, most ‘publicly’ shared photos live within the walled gardens of the service they were posted on. Instagram has become one of the worst offenders here, where even on a completely public account they throw up a dialog that forces you to log in to keep consuming. So what about our favorite photos in a public space?
<h2 id="a-place-for-your-favorite-photos">A place for your favorite photos</h2>
For us who want to share our photos openly on the web, we deserve a spot. We deserve a place where — ten years from now — we ourselves, and others, can find these moments back. A lot of the last ten years still exists within Flickr, but some of it is now hidden after people have lapsed on their Pro accounts. On top of that, it is a pretty tough place to traverse.
I believe in the value of a lightweight way to share your photos publicly, and I am excited to put my energy in to building a place that deserves our photos. This is why I started chipping away at building a service that would allow me to share just a curated sliver of my cache of 18 years worth of photos. 
It started as a static website that I generated out of a very dingy GitHub repository, and is now a prototype that allows anyone with an account to upload photos, add them to photo sets, and tag where they were taken. It is a place that is not a walled garden, and it’s a place where I am excited to (re)post anything from some great get-togethers of smart minds (at <a href="https://shoebox.photo/s/c99001g8ppo4">Brooklyn Beta</a>, <a href="https://shoebox.photo/s/8ffe01g1hnic">XOXO</a>, Build, CreativeMornings, etc.), to <a href="https://shoebox.photo/s/7d6a01gb4lkc">trips</a> that I took, to photo projects small and large.
If you’re interested in testing it out, please <a href="https://twitter.com/miekd">reach out on Twitter</a> or <a href="mailto:hello@maykelloomans.com">email me</a>.

Why Shoebox?

I have recently joined the design team at Brex, where I’ll be working on “Special Projects” (aka. big bets that we believe will have a super positive effect on our customers, starting with our mobile product.)
I have recently joined the design team at Brex, where I’ll be working on “Special Projects” (aka. big bets that we believe will have a super positive effect on our customers, starting with our mobile product.)
I decided on this role for many reasons, but two are at its center: (1) people, (2) positively impacting small businesses.
<h3 id="people">People</h3>
A crucial constant that I have found throughout life and my career is the quality of people you get to work with. Everything is better around good people.
Want to do some super fun, creative work? It’ll be better with good people. Want to stretch yourself and focus on personal growth? You’ll enjoy it a lot more if you are around good people.
Every conversation I had while getting to know Brex was excellent. The easiest way to sum up the patterns I noticed in the people I talked to: high talent, low ego, and very honest and candid about the company’s state. (It’s in hypergrowth, this comes with challenges.)
<h3 id="positively-impacting-small-businesses">Positively Impacting Small Businesses</h3>
We see small businesses horrifically impacted by this pandemic. I believe providing them with better tools is one of the most significant ways to affect them coming out of the pandemic in a positive way.
Working on a product that will allow someone to manage their small business on the go feels like a no-brainer, and I’m excited at the opportunity to improve their ability to control and get insight into their business.
And now the plug! We have a lot of work to do (across all screen sizes.) We’re actively growing the design team, so if you are a senior or staff-level designer (or have been doing the work of one) looking for a new opportunity, <a href="mailto:hello@maykelloomans.com">please reach out</a>!

Joining Brex

Have you ever found yourself in a discussion around design decisions, engineering decisions, or product direction? Have you seen these discussions go in circles or seemingly not get resolved? 
In most cases, a straightforward question can save you a lot of time: “Out of ten, how much do you care about this topic [your reasoning]?”
Have you ever found yourself in a discussion around design decisions, engineering decisions, or product direction? Have you seen these discussions go in circles or seemingly not get resolved? 
In most cases, a straightforward question can save you a lot of time: “Out of ten, how much do you care about this topic [your reasoning]?”
When I first heard this question, it sounded absurdly simple. And it still does. However, you would be surprised at how effective this question is.
Yes, I am aware that it completely oversimplifies the access you may have to external validation practices (like market research, customer research, or behavioral data.) Even with all of this work and these signals, you will often find yourself in a discussion where there is no clear direction. In these moments, it is much more vital for you to create focus and momentum for your team and yourself than to be right at the moment. 
The real goal is to develop shared knowledge and common ground between (often very smart) people who have different frames of reference, other goals, and different ways of communicating. It can allow you to save time and increase momentum, understanding, and mutual respect. 
So what are some of the results of asking how much someone cares about the topic at hand or their take on it?
<ol>
<li>You can completely short circuit an argument for argument’s sake. (If you find that you are unsure about your opinion and are only bringing it up for consideration, and score yourself at a 4/10, while your team member has thought this through diligently and scores themself at an 8/10, you just won your time back.)</li>
<li>You create a common language and learn what every one of your team members cares about. (You can ask follow-up questions like: “out-of-ten, how probable is it that you’re right?”)</li>
<li>You have the opportunity to calibrate the people with the loud voices (the squeaky wheels) against the quiet ones. And in turn, you can calibrate yourself. (Finding mechanisms to allow the quietest members on your team to be heard is deeply important.)</li>
<li>You can analyze your relationship with others and identify potential pressures that would build up over time because of endless discussions.</li>
<li>You can start predicting how specific arguments will unfold and guide other people on how to handle them.</li>
</ol>
This question is only one example of how to get there. In a healthy candid organizational culture, it is all about working together, leading with vulnerability, having a good escalation structure, etc. Ideally, you should genuinely be able to ask directly what someone’s angle is to get to a good resolution.
There is a more extensive set of questions that, on the surface, seem very simple but can have some very positive impact on communication within your team. Questions like:
<ul>
<li>“Related to other things we have on our plate, is this discussion the most important one to have?”</li>
<li>“How easy is it to revert the decision we make here?”</li>
<li>“Is there a specific signal that will help decide this? (ie. behavioral data)”</li>
</ul>
None of this is a silver bullet for every scenario, and if your organization fundamentally rejects these types of discussions, you have bigger fish to fry. However, please try them out amongst the collaborators you trust, and see how it works for you.
I plan on writing a few more of these, so if you have any stories you want to share or use help with, please <a href="https://twitter.com/miekd">reach out on Twitter</a> or <a href="mailto:hello@maykelloomans.com">email me</a>.

Speeding Up Design Discussions

Today [October 19th, 2020] marks one year of taking time off. I deeply realize I have been very fortunate to have this incredible privilege, but I must say that I genuinely didn&#39;t feel its importance until about 3-4 months ago.
This note is an edited version of a thread I wrote on Twitter which reflected on the good and the bad of a year off, as well as lessons learned.
(This note is an edited version of a <a href="https://twitter.com/miekd/status/1318237375177240576">thread I wrote on Twitter</a> that got way too long; yay, freewriting!)
Today [October 19th, 2020] marks one year of taking time off. I deeply realize I have been very fortunate to have this incredible privilege, but I must say that I genuinely didn&#39;t feel its importance until about 3-4 months ago.
<h2 id="making-the-decision">Making The Decision</h2>
Whenever I&#39;ve talked with people about taking time off, the immediate question is: &quot;How did you decide to take time off?&quot;
The story this brings to mind is that I decided against it twice. First, I almost left FB at the start of 2017 because my team and I had just finished a big project, and I was tired. And (2) I had no plan to join a company immediately after my time at Facebook. In both cases, my attention and focus were wavering, but I could do these focused sprints that were so productive it seemed I was perfectly fine... until I wasn&#39;t.
Facebook gave me the freedom to work on efforts that hadn&#39;t had a lot of design attention before. This allowed me to be out of the line-of-sight of a release cycle. I got to do some super nerdy fun work and build teams that worked on internal tooling and privacy. However, my engine was sputtering, and I wouldn&#39;t stop. 
In one instance, I was able to design work far enough ahead that I could take six weeks off (a company perk they called recharge) without much operational impact at all. When I came back to work, I had a bit of renewed energy, but it waned fast. Work was unfocused, and my life was unfocused. Yet, I couldn&#39;t at the time see my attention, my relationships, and my optimism slipping away. But I kept going, even though I couldn&#39;t get a good mental picture about what I was doing and why anymore.
Cue the departure from Facebook and a fantastic opportunity in New York at Glossier. I continued to follow a path I had laid out: aim to do great work, with a heavy focus on design, team, and company fundamentals (solving problems in predictable, systematic ways, consistent communication, career tracks, performance management, transparency etc.)
Lo and behold, my lack of energy caught up to me. (Lesson learned: even with all the optimism and excitement, I can do about 9-10 months of this) Again, my focus and the consistency of my output were waning. It became clear that I should have taken time off, but &quot;I signed up for this, and I&#39;ll be damned if I don&#39;t deliver.&quot; So I focused on hiring some of the smartest people I could find and delegated the work away that led to me having to context switch constantly.
Whenever you find a way to increase your efficacy dramatically or delegate large parts of your work (also known as &quot;hiring yourself out of a job&quot;), there is often this great Y-split that you create. 
You can either: 
<ol>
<li>define a new role and break open new scope, or</li>
<li>make a lateral move, or walk away.</li>
</ol>
I&#39;d done both at different levels of scale but never truly walked away entirely before. So there came this moment where I had the title, I had the seat, and grown my team, and delegated my role enough that either I could decide to double down and define a new scope or take myself out of the picture. And I did not have the energy to double down.
<h2 id="taking-time">Taking Time</h2>
A year ago, on this day, I had my first proper day off in 15 years. A day without a company I ran or a job I was responsible for—even if only in the back of my head. Immediately I started doing a ton of traveling to see friends all across the world. This was an absolute blessing and also the best distraction. It wasn&#39;t until I got back home in January that I forced myself to sit in quiet and open up Pandora&#39;s box of how deeply I had affected my energy and brain. I didn&#39;t want to get out of bed, I had absolutely no feelings of inspiration or creativity, and I generally disengaged from everything.
Two months later, the pandemic hit. I should have taken as a hint to embrace doing little to nothing. Yet, every day, with the smallest bit of energy, I had my &#39;productivity&#39; brain fighting my &#39;you-need-a-break&#39; brain. Every day, it was &quot;You should do something!&quot; vs. &quot;I don&#39;t want to do anything.&quot; This ended up lasting months.
I had to allow myself to do nothing, and trust to come out the other side with a clear mind. Which... is a stupendously hard thing to tell yourself.
To make sure I wasn&#39;t jumping off the deep end without any tools, I had my weekly therapy check-ins, kept up on calls with friends, ran on the West Side Highway (yay, those little mask cups that allows you to run with a mask), and implemented some basic structure to keep my sanity alive. But that was about as much as I could muster in a day.
A few months into the pandemic, it became clear I had to leave the concrete jungle and find some sunlight on the coast I had moved from. San Francisco would offer me more daylight, and I could take my car anywhere to feel a sense of movement and see the beauty around me.
<h2 id="on-the-upswing">On The Upswing</h2>
Slowly but surely, even with a city in lockdown, my regular conversations with friends, not asking too much of myself, and keeping somewhat of a structured day, gave me the desire to want to make things again.
A great opportunity came along, so—of course—I immediately jumped on it and started doing work. After a few weeks, it became clear this was too early, and it wasn&#39;t the right fit. However, this was the first time I felt my optimism, focus, and productivity come back.
This optimism was what made me finally accept that it was okay for me not to work for a bit. As soon as that became clear, my mood shifted. I focused on my personal life, which in turn (patently obvious, by the way) started tickling my creative and technical brain again. We&#39;re now at 12 months and a day, and while I don&#39;t feel that I need to work on something immediately, I have not felt this sharp and energized in about 3-4 years.
<h2 id="lessons-learned">Lessons Learned</h2>
The biggest lesson for me among all this was—and this may sound &#39;woo-woo&#39;: seeing a structured day, a quiet cup of coffee, or a workout not as a task but as something to relish. There are these things in our lives that we know we &#39;should&#39; do, but if we don&#39;t find a way to appreciate them truly, it will forever be a struggle to integrate them.
Be it working out, being mindful of your diet, meditating, managing your attention, and in this case—for me—it was challenging my assumptions and getting off of this career hamster wheel. Even though fear will tell you otherwise: with a little turbulence, you can always get back on.
However, I don&#39;t just want to write this without acknowledging the situation we are in right now. It&#39;s a cliché to say this, but times are crazy; there is macro-level stress, day-to-day life has been upended, and—on top of that—you&#39;re likely in too many (video) calls every day. 
If you have the opportunity to protect your time by taking a long stint of time off, especially after many years of work, please consider it. Plan it out, budget it, consider the consequences, learn how much it will affect your retirement, all those things.
In all of us lies this subconscious stress that we can manage, and manage, and manage until we cannot. It&#39;s like dehydration for your energy: when you figure out that you are thirsty, it&#39;s way too late.
If you made it here, thank you for your time and attention. If you want to talk more about this: my DMs are open.

Reflecting on a Year Off

Friday [September 21st, 2018] was my last day at Facebook. It was an experience of a lifetime, and I couldn’t be more thankful for it.
Here’s the note I wrote to my colleagues. I was originally going to circulate this to just friends, but with the positive feedback I have gotten I decided to use this venue to post more widely.
Friday [September 21st, 2018] was my last day at Facebook. It was an experience of a lifetime, and I couldn’t be more thankful for it.
Here’s the note I wrote to my colleagues. I was originally going to circulate this to just friends, but with the positive feedback I have gotten I decided to use this venue to post more widely.
<h2 id="thank-you">Thank You.</h2>
As hard as a decision it was to make, September 21st will be my last day at Facebook. Over the last six years, I have worked with a tremendous amount of love and energy on the opportunities this community has allowed me to be a part of.
I am grateful for the projects I have been a part of. I am grateful for every single ounce of progress we were able to make, and every launch we were able to do. I am grateful for the faith that people have put in me, the guidance that I was given, and the opportunities I have received.
Most of all, I am grateful for the bold, talented, tireless people I have had the great fortune of meeting, working with, and learning from.
As there is too much to cover about the last six years, here are some lessons I learned.
<h3 id="1-figure-out-what-you-want-to-optimize-for">1. Figure out what you want to optimize for.</h3>
Having impact for the company is your job, but what is the purpose of this job to you? How can you look back and be proud of the time you spent?
For me, I have always optimized for learning. This has put me in some uncomfortable and inefficient situations, but I can honestly look back and say I have learned from every single one.
<h3 id="2-find-your-people">2. Find your people.</h3>
We move fast. This is a hard job. Find your support system, both inside and outside of the company. Find people you can lean on, people that invigorate you, and people who aren’t afraid to be honest. I feel very fortunate to still have strong connections to the people I have worked with throughout my time here.
<h3 id="3-be-patient-yet-vigilant">3. Be patient, yet vigilant.</h3>
It is easy to want to get things done fast. It is easy to look at the past half and feel like not enough progress was made. A lot of the roles we take on, and the work we do will only pay off in the long term. So be patient and aim for the prize. However, don’t be apathetic. If you sense that something isn’t right, and you cannot shake it, figure out how to best impact it.
<h3 id="4-give-feedback-in-the-right-venue">4. Give feedback in the right venue.</h3>
Feedback is important. Being honest and calling out potential pitfalls even more so. Be thoughtful about how, and where, you give this feedback. Nobody wins if you call someone out on potential bad behaviour amongst a group of their peers.
Find the right venue to give feedback, and it will likely be more effective.
<h3 id="5-listening-is-knowing">5. Listening is Knowing.</h3>
Don’t make assumptions. Asking questions is the best way to get to know as much as you can. By asking questions, intentionally listening, and analyzing people’s position, you can figure out at what level you should have a conversation. Is this about a detail? Is this about a structural problem? Is this about strategy?
The strongest leaders I have seen move around this company have always observed and asked questions first. And if you don’t feel comfortable asking questions in a meeting, ask them over Messenger, or in a group.
<h3 id="6-pace-yourself">6. Pace yourself.</h3>
I learned this one the hard way. There were weeks where I would get on 640AM commute in, and 10PM commute out. And I definitely had the energy for it. But these things catch up on you. So make sure to pace yourself.
Nobody wins when you’re tired, when you’re on edge, and when you’re off balance. Use your PTO wisely, find ways to reduce your commute, force yourself to have lunch away from your screen.
Thanks again for all the great moments and memories. It’s been an honor and a pleasure.
(<a href="https://medium.com/@miekd/six-lessons-from-six-years-at-facebook-322a537b6474">Originally posted on Medium</a>)

Six Lessons from Six Years at Facebook

New Year&#39;s resolutions are hard. Many people make them every year, and few actually succeed. I&#39;ve personally never been successful at keeping a New Year&#39;s resolution, primarily because the magnitude of the task at hand seemed so big, and &quot;life got in the way&quot; (ie. other things took priority to the resolution that was established.)
With that said, I thought about approaching New Year&#39;s Resolutions as a design problem.
New Year&#39;s resolutions are hard. Many people make them every year, and few actually succeed. I&#39;ve personally never been successful at keeping a New Year&#39;s resolution, primarily because the magnitude of the task at hand seemed so big, and &quot;life got in the way&quot; (ie. other things took priority to the resolution that was established.)
With that said, I thought about approaching New Year&#39;s Resolutions as a design problem.
<h2 id="the-problem-with-new-years-resolutions">The problem with New Year&#39;s Resolutions</h2>
New Year&#39;s resolutions are often ineffective approaches to an end goal. New Year&#39;s resolutions are about aspiration and behavioural change. The format of a New Year&#39;s resolution is a statement that expresses a promise or a solution. It uses an arbitrary point in time, and an arbitrary length of time to do this. Most of them are also formulated in large, ambiguous ways (&quot;I want to lose weight&quot;, &quot;I want to stop smoking&quot; etc.).
<img src="/static/notebook/new-years-goals-monthly-resolutions/01-New-Years-Resolution-Timeline.png" alt="">
To me, there are three major problems with New Year&#39;s resolutions:
<ul>
<li>A New Year&#39;s resolution is articulated as a promise or solution, and does not express the problem you actually want to solve.</li>
<li>Because of this, a New Year&#39;s resolution does not express the motivation behind the resolution, or a &quot;why&quot;.</li>
<li>The time horizon is too long. New Year&#39;s resolutions don&#39;t account for unexpected changes, like jobs, travel, partners, interests etc.</li>
</ul>
<h2 id="reframing-new-years-resolutions-to-goals">Reframing New Year&#39;s Resolutions to Goals</h2>
This is why, in the last eighteen months, I&#39;ve reframed it for myself. It breaks down to two elements:
<ol>
<li>Set clearly defined goals with an arbitrary time horizon (1 month, 3 months, 6 months, a year), and ask yourself why you want to achieve these goals.</li>
<li>Use monthly resolutions to work towards, and check in on, these goals.</li>
</ol>
<h2 id="set-clearly-defined-goals">Set clearly defined goals</h2>
Over the last eight years, I&#39;ve been reasonably good at consistently working out and not eating too many bad things. I would have periods in which I would get really in to running, or cycling, or interval training, but all slowly faded. There were triggers that have caused these positive behavioural change, but none of them lasted.
In June of 2015 I set myself one personal goal to finish the year with: Become more fit. How? (1) Work out more, in a consistent way, and (2) be intentional about the things I eat. Why? I want to reach and extend the peak of my fitness for as long as I can. (or: I&#39;m getting older and I&#39;m actively going to make sure I do it the right way.)
The tool of choice? Monthly resolutions.
<h2 id="time-box-a-step-towards-the-goal">Time-box a step towards the goal</h2>
For the month of June 2015 this meant:
<ol>
<li>Work out at least 3 times a week.</li>
<li>No bread, pasta, white carbs, processed foods etc.</li>
<li>Not more than one alcoholic drink a night.</li>
</ol>
These were simple rules to follow, the one month time horizon is a small commitment, and this monthly approach allows for faster iteration and continuous success. If successful, these rules were going to roll over to July.
<img src="/static/notebook/new-years-goals-monthly-resolutions/02-New-Years-Goals-and-Monthly-Resolutions.png" alt="">
🚀💪🏻 → 😬😱 → 😎👌🏻
And they were successful. Yet halfway through July I had to help with a project in New York City. And while I could keep up the workout rule, the work priorities and distractions of New York got the upper hand. With monthly resolutions, July was lost, and I was able to pick it up again in August. Into September, then October. And whoops, because my birthday is in November, basically all the rules were broken again.
All time horizons are arbitrary. With New Year&#39;s resolutions, I might have had more resolve. But most likely I would have folded on them completely.
<h2 id="monthly-resolutions-are-small-commitments">Monthly resolutions are small commitments</h2>
Fast forward, I restarted the rules in January, but with a change to 4 workouts a week. I succeeded, and switched to 5 workouts a week in February.
Nowadays, it feels off when I don&#39;t work out more than 3 times a week. Monthly resolutions have allowed me to change my behaviour in a flexible, iterative way throughout the year. Beyond the personal health and fitness changes, I&#39;ve set goals for quality time spent with friends, consuming less things from the internet, travel, exploring hobbies, reading and improving my apartment.
The end result of all this is having done over 200 workouts, spending quality time with a small set of close friends, spending a couple of weeks traveling and (almost) completely disconnecting from work, picking up and getting halfway decent at tennis and tripling my reading (which is only an abysmal six books for the year, but still.)
<h2 id="continuous-iteration">Continuous Iteration</h2>
One of the key strengths of monthly resolutions is continuous iteration. If you don&#39;t succeed for a month, that&#39;s okay. Take a cheat day. Take a cheat week! Hell, challenge if you even should be doing some of your resolutions. Adapt.
If you are successful, consider if you&#39;ve been challenging yourself enough. Maybe you easily cut the amount of time spent watching TV. Should you even be watching TV? Maybe you breezed through taking a 2 hour walk every weekend day. What about a hike every weekend? Maybe you have an extremely busy life and found a way to meditate for 10 minutes a day, what about making it 15 minutes?
If it doesn&#39;t work, it doesn&#39;t mean you failed. It means you need to reflect and consider what you should do different next time. If it does work, it doesn&#39;t mean you didn&#39;t challenge yourself hard enough. But it might be worth considering if you did.
I hope some of you try this. And if you do, please let me know how it is working for you.
<img src="/static/notebook/new-years-goals-monthly-resolutions/03-New-Years-Resolutions-vs-New-Years-Goals-Summary.png" alt="">
(<a href="https://medium.com/@miekd/new-years-goals-monthly-resolutions-39e6e91d9da0">Originally posted on Medium</a>)

Hi, I'm Maykel

Photography

Notebook

Why Shoebox?

Joining Brex

Speeding Up Design Discussions

Contact