productivity :: balance :: freelancing :: notebooking
Pomodoro Hacks

Pomodoro Hacks

You’ve likely heard of the Pomodoro Technique. Invented by Francesco Cirillo, it’s been floating around the nerdisphere for years. If it is unfamiliar to you, here’s the scoop on how to pomodoro:

  • Choose a task to do
  • Set a timer for 25 minutes (traditionally an analog, tomato-shaped timer)
  • Focus on the task until the timer buzzes
  • Take a 5 minute break
  • Repeat

Mr. Cirillo has a nice description on his site, if you want more details (though there aren’t that many more details).

It works pretty well, even though it’s simple to the point of obviousness. Sometimes you just need someone (or a tomato-shaped timer) to tell you to sit still and focus for 25 minutes!

I’ve been pomodoro-ing off and on for years. It’s a tool I pull out when I especially need to focus or have been procrastinating. It really does trick your brain effectively. How bad can 25 minutes be? (And then you start your second 25…)

Here are a few pomodoro observations, hacks and ideas I’ve gathered in my tomato travels:

Bigger tomatoes

I saw Ed Gandia give a talk a few years ago and he suggested that you re-adjust your pomodoro increments to be 50 minutes with a 20 minute break in between. He argued that you cannot get into a state of flow in 25 minutes — or you just barely get in and then the timer goes off. In my experience, this is pretty true, especially when you’re doing a creative task like writing, designing, or even coding. I’d give 50-minute sessions a try (though I do 10 minute breaks to keep the hours even). Even if you only manage two of them, you’ll get a heap done. If you manage four in a day, you’re a productivity superstar. (You may want one longer break in there — time for a walk or something refreshing — to keep you from getting too knotted up).

Focus at Will

This tip, is, again, inspired by the same Ed Gandia talk. He recommended trying a SaaS called Focus at Will. I did, indeed, try this app, and kept my subscription to it for a year. I may or may not re-up it sometime. Focus at Will is a music player with a timer well-suited to pomodoro sessions. The music, claim the FAW folks, is scientifically engineered to increase focus and productivity. That may well be. But as a bit of a music nerd, I have to admit I got a bit bored with it after a while (and isuper-irritated by the segues in the classical playlist). They don’t add new playlists very often, and there were only a few I could bare to begin with. That said, the few that I took to, I did use quite a bit. and it became quite pavlovian for me to hear that music and get to work. Hard and fast. Regardless of other scientific merits, the habit trigger of listening to FAW worked brilliantly.

Once my subscription expired, I decided to make some FAW-style playlists of my own, using Spotify. Sure, they’re not backed by research, but they do in a pinch. I used most instrumental post-rock music, and made each list as close to exactly 1 hour long as possible. This may not be the kind of music you like to focus to, but it works pretty well for me. I also like certain kinds of classical for this purpose. I know a lot of people like EDM for focusing (or some sub-genres of it that I don’t even know the names of, because I’m too old) — and I did like the EDMish playlists on FAW, though I haven’t made my own. Spotify does offer a bunch of premade ones in electronic genres — as I’m sure, do other playlist curation services. I’ll include links to my slightly random Spotify 1-hour focus playlists at the end of this post.

Sweating the small stuff

One of the situations that is most likely to cause me to procrastinate is having a big list of little to dos. These are all those kind of annoying things that pile up but they really need to be done. They each take somewhere between 2 and 15 minutes. Writing and responding to emails, finding files, looking up information, digital filing, making little tweaks to this and that, admin stuff… you know the kinds of tasks. The odds and ends. No way to get into a state of flow with that junk!

To convince myself to plough through, I make a game of it. Ok, I use the word game very loosely. It’s not really that fun, but we’ll just pretend it is. Equipped with a checklist with actual checkboxes and a pen, I set a short pomodoro of 20 or 25 minute and see if I can check off all the “little things” before the bell rings. I go as fast as I can and weirdly, but the end of the session, I’m often on such a roll that I put off my break while I finish the last few things. Maybe I’m gullible but this trick works pretty well for me!

And a bunch of quickie tips

  • Search your mobile app store for “pomodoro” and you’ll find lots of free and paid timers for your phone. Somewhat less awkward to carry around than a plastic tomato.
  • Pomodoros are perfect for house cleaning, especially if you’re a reluctant chore-doer like I can be. I do sessions of 20 minutes hardcore cleaning followed by 10 minute breaks to watch a video, drink a coffee or otherwise be sedentary. 20 minutes is pretty much ideal for a sink full of dishes, a basket of laundry, or, sigh, a dirty bathtub.
  • This one’s a bit obvious, but don’t forget to stretch during your breaks when you’re computing. I’m prone to forget as my right forearm, shoulder and trapezius will tell you.
  • I haven’t tried it yet, but I’m considering making phone-meeting pomodoros for certain people who tend to reiterate and go on and on when they get me on the horn. The tactful way to do it, of course, would be to say “I only have 20 minutes, then I will have to go” at the start of the conversation, but it is tempting to have the very loud tomato ring into the phone!

Do you pomodoro? Have any good tomato tips?


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New Year Mindmap SeriesPart 4: How to

New Year Mindmap Series
Part 4: How to

In Parts One, Two, and Three of this series, I told my stories about using mindmaps to help sort out what’s happened during the year that’s ending and making a plan for the year that’s about to start — and about, how, as I recovered from a very bad depression, I was able to use these mindmaps more productively and go from vague ideas to actual action plans.

In this post, I’ll outline the steps for making your own year-end mindmap. Give it a shot, it’s cathartic and satisfying, and can be really fun.

Step by step

  1. Get some big paper. You can tape sheets of regular paper together, use packing paper or butcher paper, use the back of wrapping paper, or buy a roll of cheap “easel” paper for kids.
  2. Find a place to work. I roll out paper on my big dining room table and tape the corners down. You might want to work on this over the course of a few days, so if your kitchen or dining room table is used for other things — like dining — you might opt to put your paper up on a wall or the back of a door (and work vertically).
  3. Gather some writing implements that make you happy. It might be your favorite black gel pen, it might be a set of colorful markers. Whatever you feel excited to write with at the moment.
  4. Pleasant-i-fy your work environment. This is going to be a longish, inward-looking creative marathon, so get comfortable. As few distractions as possible, some nice music, mood lighting, coffee, tea or a glass of wine… you know the drill. As the nice man on my sleep meditation app says in his soothing Scottish accent, “This is your time. Time for you.”
  5. Center yourself. You can take this literally, figuratively, or both. For the former, write something at the center of your paper that will be the topic of your mindmap. I usually put the date of the coming year. But anything’s fine. For the latter, close your eyes, take a deep breath and clear you mind of other things.
  6. Start one way or another. You can begin by making the first bunch of “main branches” that occur to you. Maybe there are a bunch of areas of your life you know you want to brainstorm about (family, health, money, home, work, etc.). Make a branch off your center for each of those. Or, maybe you want to just dive into them one at a time. Draw your first branch and start making twigs off of it.
    • I find it pleasing to use a different color for each branch and its twigs, but you don’t have to, by any means.
    • I find it handy to draw out a bunch of main branches, so that even if I’m focusing deeply on one, I can jump to another to stick in something that occurs to me.
  7. Keep going until you’re empty. You can take breaks of course. I usually do this over several days, myself. But the idea is to draw twigs out of each topic for everything that occurs to you until you don’t feel like you’ve left any direction or thought unturned — and maybe, though you shouldn’t pressure yourself — you’ve come up with some stuff you want to pursue.
    • Be as un-self-censoring as possible. Let yourself go. Don’t worry what it looks like. Don’t worry if it’s a huge mess and you tape extra bits of paper on or cross things out. Don’t worry if it says stuff that, if you were to look at objectively, you might decide is dumb. You can be as whimsical as you like here. Write down possibilities that don’t seem remotely feasible. Write down things you want to remember even if they don’t seem important. Get everything out of your head, and let that stuff spark other stuff. You don’t have to show this to anyone. You don’t have to read it over when it’s done, and you don’t have to keep it. Just GO.
    • You can create an offshoot for a topic that reviews what happened in the past year. It could contain just the facts, or also your interpretation and analysis. You can even ask yourself questions within your map. Mine often have sections that are a bit like flowcharts with boxes asking “Why?” or “What if?” and multiple possible answers.
    • You can focus only on the future if you’d prefer. I like to make min-branches for all the possible futures of a thing, exploring the feasible and fantastical options. Maybe a goal for the year is to exhibit art publicly. I could have a branch-lette exploring putting a photograph in a low-stress local art show at a community center and I could have a branch-lette figuring out my guesses as to what it would take to put on a highly publicized solo exhibit in a city gallery. And other branches looking at options in between.
    • You can mix new years resolutions with vague ideas. You don’t have to commit to anything in this map. Just let it all out.
  8. When you don’t feel like there’s anything left in your head to write, wrap up in one of these ways:
    • Look it over. Highlight the items you want to actively pursue. Transfer these to your to do system. You might have items that go with different project lists, or a “someday/maybe” list, next week’s to do list or a future log. Put the items where they go so you’ll be sure to take care of them, or at least reconsider them at the right time.
    • Or, don’t look it over at all. roll it up, wrap an elastic around your scroll, write the date on the outside, and store it away somewhere. Look at it next new years and see what happened and what didn’t. Consider it your transcription of possible intentions.
    • Or, keep it on your wall and check in on things throughout the year. Add notes, check things off.
    • Or, think of it as a exercise in emotional release and burn it up in the fireplace. Or paper shredder. Or tear it up and recycle it. Use it for hamster bedding.
    • Or, do whatever feels right to you. There are no rules.

Big paper is your friend

Of course, the mindmap technique works for lots more than just annual reviews. I make mini ones sometimes to weed through tricky problems or to generate ideas — from the technical to the creative to the emotional.

I grab big paper when I start complicated projects and make all kinds of hybrid mindmap/diagram/bullet list messes to sort things out and ideate. I’ve done this for websites, for a film I was working on, even for ways I wanted to improve my apartment. The big paper makes me feel like I have more room for a problem and permission to think more expansively.

I know someone who always has an easel and a pad of big paper set up in their workspace to make notes and lists and work through problems. You know I love my notebook, but sometimes big paper is the magic you need.

I hope this has given you some ideas or the motivation to roll out some bigger brainstorms as the year comes to an end.

I’m looking forwarded to doing a new mindmap this year, during the last week of the year, which is coming up soon. I’ll let you know how that goes. How do you use mindmaps? Do you have a yearly wrap-up/planning ritual?

Happy mapping!

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New Year Mindmap SeriesPart 3: Getting Productive

New Year Mindmap Series
Part 3: Getting Productive

Colorful clouds

If you read the “Spoilers” section in Part 2 you know that I did a lot in 2015. Maybe not everything I hoped for, but I made a lot of progress. By December, I was ready to look at 2016, and had a lot of ideas.

I got out my big paper from the kid’s department again, and taped a stretch of it to the dining room table.

I was moving fast, being messy. I was using a mix of different markers I had around (Crayola, Bic Mark-it, highlighters — this is a notebook blog, I have to tell you what markers I used). I drew demented clouds around the topics of main branches of thought, and I kept adding branches in later, when new ideas came up. I think it may be a good sign, when something like this is disorganized… it means I was coming up with new stuff and thinking fast.

Like the year before, main branches of the map were divvied between “life areas” like Finance or Home and random topics like Content Marketing (honestly, I’m not sure where I was going with that at this point, but I seemed to have been excited about it).

Some topics that were one branch the year before, became multiple ones this year — notably, several different branches for areas of my business. I think this is where I started really codifying the difference between work in my business and work for my business. Of course, I’d always done both, for my current company and for the ones I’d run before, but I never thought so separately of the client vs. non-client activities. This mindmap may be where I started referring to non-client work as my “meta” work. (Hey, it makes sense to me.)

I added some new side projects I was working on, and, I think, significantly, when I look at it now, added a couple topics that are about doing things purely because I enjoy them (e.g. Hobbies) not out of any obligation or goal-seeking.

Getting granular

Looking back at this map after looking at the one for the year before, I see I just had so many more ideas — and “actionable” ones at that. (That is an annoying word, I apologize). Even in boring topics like Finance, I had lots of plans and aspirations. I even brainstormed plans for different client projects in particular — how to make them better, how to make them happen faster and more efficiently — like I cared. Sure, I’ve always done the best by my clients, but what a difference from a few years before!

I even have a small Goals section there, with some overarching wishes for myself and my year (“Stay healthy”).

There are places in this map where there are ORs and I give myself options as I come up with better ideas. There are also some very specific lists of steps to take for the better ideas, labeled 1, 2, 3, or A, B, C.

It’s got all the good parts of other mindmaps, the brainstorming and probing into ideas. Asking a few “why” questions and coming up with alternate solutions to reframe sticky issues. But what I like about this one, in particular, is that after I felt done, that I’d spewed out all the stuff in my brain as Mr. Allen would have one do for peace of mind, I thought to myself, “there’s some good stuff in here.” And I went back with a yellow highlighter and found all the things I really wanted to do — the things that were “action steps” — and I transferred them to real to do lists in my notebook.

So, this year, when I rolled up my mindmap on New Year’s Day, and stuffed it in my basket of scrolls, I felt like it wasn’t just a catharsis, it was also a plan. Having come from a place, a few years ago where I didn’t feel capable of making a plan, or having goals, or thinking about anything beyond the bare necessities, I think this is cheery progress.

In Part Four I’ll list out some tips for doing your own annual mindmap.

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New Year Mindmap SeriesPart 2: Starting to Evolve

New Year Mindmap Series
Part 2: Starting to Evolve

Checking in (with me)

By December of 2014, I was in a better place emotionally than I had been in Part 1, and with my business. I was still working hard to pay the bills and living on less than was ideal, but at least things were moving forward. I had new clients, new potential opportunities, new side projects, and new ideas. I may have even been a little excited about the new year to come. It was time for a new mindmap.

I went to the art store and bought a cheap roll of white paper (in the kid’s section) and taped a big swath of it down on the dining room table. I got out my Crayola markers. I wrote “2015” in the middle of my canvas and decorated it with stripes.

This time, feeling more in control of my life, I made branches off the new year of representing areas I wanted to think about and work on. And I even gave each its own color.

Not all of these big branches are strictly congruous — they’re not each a major area of my life, per se, like you’d use in a “Level 10 Life” exercise. It’s more freeform than that, more intuitive and brainstorm-y. Some of the branches are traditional life areas like “health” or “finances” but others are projects I wanted to pursue or was working on. Others, like “art” are life areas important to me but not everyone (I can see my significant other putting “code” in that same slot!).

When I look back at this mindmap, it looks so simple. So many of the ideas and goals on it seem rudimentary now… the obvious steps you take as you’re climbing the bottom rungs of Maslow’s pyramid of needs. But that’s what I was doing in a lot of ways. I was rebuilding my life after a major upheaval and depression. I was re-establishing myself in a new world without job-security (i.e. working for myself) and cleaning up messes that had happened when I was depressed. In a lot of parts of my life, baby steps were in order.

In other parts, I was exploding with creative ideas. I was working on a book, an app, planning a documentary film, working on a bunch of art projects, considering hosting a craft night for friends at my house, amongst other things. I can tell I was excited about some of these things, because my handwriting is hard to read in places.

This map for 2015 is relatively simple compared to others I’ve drawn. It has fewer branches and twigs and diversions than usual. The section on work is pretty light… I was still recovering from burnout to some degree and doing what I needed to do. But I can tell I was getting excited about side projects (and possibly monetized side projects) and looking at ways to be enthused about making my living again.

I was at a place where I only had a certain number of things I could handle alongside the basics. I think I got them onto the paper, wrote some details, wandered around the ideas a bit and I was done. That year, that was what I needed. December ended, I rolled up the map and stuck it in the basket in my office.


The point of these mindmaps is not accountability, it’s brainstorming, dreaming and capturing. But I can tell you, looking back on this, that of all the big ideas I was excited about that year, I didn’t actually complete that many the way I thought they’d happen. (And I think that’s to be expected, psychics excepted).

  • I did finishing writing the book I was going on about. Someday I want to do a revised edition though, angle it differently and actually promote it.
  • I did go quite far down the path with the documentary I wanted to make. I did months of research, got some filming permissions, asked some people to help, took quite a few classes in filmmaking skills I wasn’t up to par on, planned the narrative (on a big paper!) and put a lot of effort into it. Then I decided it would be a boring-ass documentary that no one would like and shelved the project. A lot of this, I wouldn’t have known without all the research I did. I was looking for certain kinds of stories to tell, and I couldn’t find them. I am glad I learned all that I did, going through this process, and I hope I do manage to make films eventually. Maybe even come back to this idea somehow. Between what I uncovered in my research (or failed to) and my personal psyche at the time, it just wasn’t the right thing or the right time. But let’s chalk it up as a stepping stone to the next one.
  • I worked on some of those art projects. I got into Urban Sketching for a while and will come back to it now and then. Some of the other art projects I would definitely consider to be on my backburner to do list.
  • I traveled to some of those places (the easy, cheap ones).
  • I worked on the app idea I had with my SO. We got pretty far with it before deciding that an app was entirely the wrong format for what I wanted to do. But collaborating on something like this was a new and good experience for us, and we both learned a lot.
  • I got my finances more in order.
  • I did not read War and Peace in 2015. (But I did read it in 2016!)
  • I’m still planning on having people over for craft night.

And I don’t feel bad about the things I wrote here but didn’t do, or didn’t finish. These ideas were all MAYBES, with different degrees of importance, probability and feasibleness. Some have since become unimportant or uninteresting to me, a lot of them are still burning bright or burning dimly somewhere in my notebook. Point is, let yourself explore the possibilities for your possible future. You don’t have to play by the rules you write.

The annual mindmap story continues in Part Three.

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New Year Mindmap SeriesPart 1: A very good process that was born out of a very bad time

New Year Mindmap Series
Part 1: A very good process that was born out of a very bad time

The seed of an idea

Sometime in the aughts, I became intrigued with the idea of doing a year-end review and planning my upcoming year. I think reading Getting Things Done had something to do with it, though, off the top of my head, now, I can’t even remember what Mr. Allen’s recommendations are for summing up your year and planning the next one.

I know that Chris Guillebeau had a lot to do with it. Somewhere, in the early days of his blog, he talked about his annual review process — and I was so terribly impressed. And intimidated. Although he’s a writer, and very creative to be sure, he does get very analytical about things in a way that doesn’t necessarily connect with how my brain works. He gave out a free spreadsheet to help you review your year and plan your next year the way he does. I studied this. I read all the comments. I wished I could think that way. But when I tried to think about what happened in the past year, my mind went blank. When I tried to think of what I wanted to accomplish in the next year, I had no idea.

I thought there was something wrong with me. I thought I should be able to do these things — and that if I couldn’t, my brain was broken. So I put it on the backburner, and, each year, when Chris blogged about his yearly review, I felt kind of inadequate and dissatisfied and carried on.

A deeply personal tangent

I can say, in retrospect, that I was very wrong in my take on all this. My job involved inventing and streamlining processes for getting things done at the design studio in which I was a partner. The rest of the time, I was using design thinking and analytical frameworks to solve problems for clients and design stuff for them. Part of me knew I was very good at this. But part of me couldn’t get beyond an extreme negativity toward myself and my self-declared deficiencies.

Things got worse. And I’m not talking so much just about my inability to conduct an analytical annual review at the moment. Though we’ll come back to that.

A complicated series of events happened in my work life. It was the culmination of a bad situation that had been brewing for years. The inevitable explosion and flying debris.

I felt like every day was a fight, a trauma, a crushing blow. It was thorny, litigious, and really, more than I could take in my already deflated state. But I had to take it, and I had to keep on earning my living. And I had to keep a brave face for the outside world of my design clients, keep on doing good work for them and give the impression that everything was fine.

It took a couple years to get free from the mess. I started a new company. I handed out my new business cards and smiled, and started the process of drumming up new business.

But on the inside I was intensely burned out, and more depressed than I’d ever been, despite a lifetime struggling with depression.

I didn’t think I wanted to design anymore. I didn’t think I had a single drop of interest left in it. And I didn’t know what I wanted to do instead, or how I would find the motivation to do anything beyond the absolute necessities.

The Depression Map

It was the quiet week between Christmas and New Year in December of 2012, and I felt like it was some kind of breaking point — I would like to say turning point, but at the time, that’s not how it felt. My brain felt full, foggy, and overwhelmed. My inner monologue was on a non-stop blather that was painful to absorb. I knew I had to get some stuff out of my broken brain and look at it and see what could be done.

I had recently gotten some dieline proofs for a custom folder project that were still sitting around. These were huge sheets of paper from a plotter with black and white diagrams on one side. I flipped them over and taped them together. I laid out the huge piece of paper on my dining room table and picked up a Sharpie. In a sort of random place on the paper I scrawled Present/Future and put a box around it. Then, realizing, probably in a self-castigating way, that I should take a good look at what I’d been through over the 2012, I added, + Past Year and Lessons Learned.

Center of 2013 Mindmap

I picked up my favorite black gel pen and I was off. I just started pouring stuff out, and putting it in boxes, then, drawing arrows to whatever occurred to me and writing more words and boxes. More arrows. More words. More boxes.

There was no sense of organization or order… it was pure brainstorming, and totally uncensored. If something connected, I drew an arrow. If something didn’t fit, I put it somewhere else and drew an arrow.

I won’t lie, looking back on this mindmap is painful. It is full of harsh self criticism. It is full of accusations leveled at myself with no chance of anyone defending me. But it’s also full of two really good things: questioning and blue sky ideating.


Maybe you’ve heard of the Five Whys. Although it’s touted in lots of business contexts, it’s really as simple as thinking like a toddler until you get to the crux of a matter. You are not satisfied with the answer to the answer to your first why question — you question that answer with another why question. And that is what I did with many of my boxes and arrows. I questioned why I felt certain ways, and then asked why again. And then asked why again. Until I found something deeper — not just the negative self-talk that was playing on a continuous loop, quick to jump in with a obviously, it’s because you suck! answer. I don’t know if this helped me to feel better about myself, but at least I had some better truths down on paper than the lies I’d been repeated internally, and that has to be a step forward.

I also asked why to questions about things I was doing, planning to do, had done, or might do. Despite my depressed haze, there was a smart part of my brain somewhere that knew I needed to think about things differently and to reframe.


I didn’t feel like I had a lot of creative energy — or any, really — but I forced myself to remember projects I’d wanted to do back when I was in a better place. I forced myself to think back to things I wanted to do when I started college, or things I did in my spare time in high school. I strained to remember answers I might have given to what do you want to be when you grow up? before I had. I wrote these things in boxes and explored them the best I could. I suggested to myself that maybe I should somehow make the short film I’d written a screenplay for. I see I noted some favorite film directors — perhaps I was going to turn up on their doorsteps… I don’t know. I tried strings of boxes with different directions I could take my business in, trying to convince myself that the world was my oyster, even though I didn’t feel like it.

I’m sure I shot lots of my own ideas down in places, but I tried to at least give them a chance first. Writing these things down put me under no obligation to do them or to do anything. I just wanted to get the gunk out of my head.

How Big Paper Helped

This was not magic. I did come up with a lot of ideas, and I did, probably more importantly, refute some of the junk I was telling myself with very sound strings of causation that helped me understand what was going on in some kind of way.

Writing and writing and writing on that big paper, that was just not going to run out of space no matter what (and I could tape more on!) was cleansing. The actual physical process of doing it was meditative, even if some of the material I was writing was disturbing.

I worked on this thing for the better part of a week. My first pen ran out of ink and I took up a second one. I just kept going and going until I could thinking of nothing else and felt spent. Empty. A bit better.

Ultimately, it took time and therapy to really feel better. The further I got away from the bad situation that had led me to this dark period, the better I was. I kept on going with my new business and somehow, I eventually felt less burned out and more interested in design again.

One helpful thing I learned from that mindmap was that decisions are up to me. Before I drew out so many options and possible futures, I had felt like a victim. I had felt trapped, obliged, non-autonomous. But that was just a cage I’d forced myself into. It’s important to remember that any box can have lots of different arrows coming out of it, and you can choose to ignore the ones that lead to other boxes that don’t feel right, or don’t come from a place of progress and positivity.

Up Next

That was a rough time, and I don’t know if what I’ve written is remotely helpful. I know lots of people suffer with depression and feelings of burnout, so I hope that it gives you some ideas of how to reframe — or at least play with big paper. In Part Two I’ll talk about how this year end mindmap series evolved for me over the years that followed — and I promise, they are much happier stories!

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