Chris Hannah


Playing Around With Experimentation and Challenges #

Setting yourself goals can be an excellent way to push yourself towards a target and keep yourself heading in the right direction. But something I’ve discovered recently is that breaking a goal down into actions and turning them into challenges can be very beneficial.

The first question that comes to your mind is probably, what’s the difference between a goal and a challenge?

My answer to that would be that your perspective changes when you have a challenge rather than just a goal. Because goals usually don’t come with any information on reaching them. They’re only a target that you would like to achieve, and the journey is yours to figure out.

Something I’ve discovered relatively recently is the benefits of setting yourself challenges and using experimentation to improve skills, make informed decisions, and ensure that you stay on track.

What Makes a Good Experiment?

In my opinion, a good experiment has a clear goal in mind and a way that you can track progress. I also think it helps if there is a planning stage before a challenge is set or before any experimentation is started.

From a goal, you should be able to extract actionable tasks to help achieve that end goal.

For example, I had the goal a while ago to sort my email out and build a system that worked for me. As a goal, I would probably write it as “I want to have a better email system”. But instead, I broke it down and examined what exactly it was that I was looking for.

Turns out, I didn’t want a whole new email system. I just wanted to deal with the one address/account instead of the three I had previously. And to have an automated mechanism that filtered junk, sorted some valuable but not urgent emails, and kept my inbox for anything that I either had to deal with relatively soon or manually organise.

Once I did that, I set myself a fixed duration of 1 week and got on with my experiments. I also found that keeping a log of my decisions and opinions helped keep me on track too.

So What Are the Benefits?

I’m sure there are countless benefits to setting yourself challenges, and experimenting, rather than just introducing a goal. But at least from my perspective, here’s what I’ve found:

It’s easy to track progress. Especially when you keep records throughout the process as you make decisions.

It keeps yourself honest throughout the experimentation as you have a clear goal in mind and actions that should get you there.

Making informed decisions become more straightforward. If you perform an early analysis and identify your requirements early on, the decisions you make during and at the end of the process are more informed and more likely to be based on logic than your current thoughts or emotions in a particular moment.

Challenges I Have Set for Myself

Since really thinking about this idea of using challenges, I’ve set myself two of them. First, to find an email system that suited me, and more recently, to explore the market of writing apps to see if they fit my needs.

The email challenge was rather strict. I had a clear goal of fixing my email system and requirements that I wanted to meet at the end. And I also set myself a week to complete the challenge. I think I benefitted thoroughly from developing the initial requirements, as I found myself veering off the path a few times, but I was pulled back after re-reading my original plan.

I think that keeping a log of my decisions throughout the week also helped. Because although there were benefits of being honest to myself, I was left with a record of my thoughts and decisions at the end of the week as I tried new things. Which meant I could do better analysis at the end and make a better final decision.

The challenge to find a new writing app has been a more flexible one. Mainly since it was more exploratory, I wasn’t aware of each app’s intricacies, or in fact, what apps were available. So I went in with an open mind and precise requirements (which were refined over time) and decided to test a few apps until I thought there wasn’t any more left to try out.

In retrospect, I think I would have benefitted from some more limitations. For example, coming up with an early list of apps and doing a basic research level. Because that would have filtered a few choices out early on.

This kind of reflection is another aspect of experimentation that is also important since it can only improve future challenges’ efficiency and success rate.

Final Thoughts

By breaking down goals into steps and setting yourself challenges, I think you’re more likely to take action and actually achieve them. And by doing controlled experiments with fixed criteria, you’re more likely to finish with usable information that can help you make more informed decisions.

I want to explore challenges more, and I think I’ll be doing some more myself. Maybe less around technology choices and more to do with life in general.

I’m interested to see if anyone else has used challenges and how useful they’ve been. So if you have any past experience, I’d love to hear it.

Experimenting with Email #

I’ve been annoyed with email for a while, and I wrote recently that I wanted to find a new way to deal with it. I was mainly thinking about services like Hey, but I was also concerned that it’s essentially an email replacement, not an email service that can be linked to other accounts or clients. So I had some thinking to do.

I decided to try and keep a log of my thinking while I tried various things, and then this log began.

The main reason behind keeping a log like this was to keep me trying new things. Even if it was a small tweak, just try one thing and see if it works. And at “the end”, I could see my thought process behind the decisions, and the steps I made. I think this is important because I might have made a decision based on a whim, rather than treating it objectively.

There’s also the fact that I find experiments fun, and it might be fun for other people to see my thought process.

Current State

I’ll start with the current state of my email solution. I have three email addresses, my “primary” email address which is on iCloud, a Gmail account, and also a G Suite account which is linked to this custom domain.

Ideally, I want to switch to using one address, the G Suite one, but I know there’s a lot of emails going to the other accounts. So it might be a painful process.

I also want some sort of system of organisation or automatic sorting. Because even if all emails go to one account, not all of them are important. And eventually, I want an inbox that has only important and urgent emails.

So now that’s what I have currently, and also a few ideas for where I want to end up.

Monday, 25th January

Entry 1: After many recommendations, I signed up to SaneBox. I connected all three of my email accounts.

Entry 2: I shortly realised that dealing with SaneBox folders on three accounts would be a hassle. So I set one of my email addresses (least commonly used one) to forward to my ideal address.

The plan is to write off the third address by slowly dealing with all forwarded emails until none come through. Then I can focus on going from 2 to 1.

That leaves me with this:

Tuesday, 26th January

Entry 3: Today I made the decision to remove SaneBox from my iCloud account, leaving it only enabled on the email I want to use long-term.

I plan on slowly moving important accounts and information to my desired address as they arrive in iCloud. Although I’ll have to be aggressive with deleting junk emails when they come in since I want to be able to keep on top of that account still.

Entry 4: I’ve seen a few emails being picked up by SaneBox and placed in the @SaneNews folder, it seems to be fairly accurate.

Entry 5: Strangely, it’s becoming easier to deal with emails in my iCloud account. Maybe it’s because I know I plan to eventually stop using that account, but whenever an email comes through that I like, I tend to quickly switch it to my ideal address. And the same with emails I don’t want, they either get unsubscribed from, placed in the junk folder, or deleted.

Wednesday, 27th January

Entry 6: My use of email seems to have been whittled down to 6 places, which are probably quite predictable:

To be honest, I’m not sure if I’ll need to keep @SaneNoReplies around since I’ve only glanced at it once. And I can’t remember a time where I’ve needed to wait a long time to receive an expected reply.

But it leaves me thinking that right now may be a good idea to try out a few email clients. Since I’m not exactly doing anything complicated. Thanks to SaneBox, everything is handled by moving emails between folders, which I assume every email client can do.

Entry 7: It’s time to check out Spark. After a small amount of customisation, I think the macOS app will suit me. I slightly prefer the design to the built-in Mail app, although that’s not a big enough reason to switch. But I do like how the sidebar only contains the inbox and favourite folders. It annoyed me that inside Mail, all accounts would be visible. Which was annoying if there was an unread email in the junk folder because for some reason it thinks that’s important and shows it next to the account name.

I tried Spark a long time ago and didn’t quite like it, but this time I’ve turned off a few of the features that got in the way. Such as showing avatars, smart notifications, calendar, snoozing, and a few more. It’s left me with quite a modern email client.

Although I did leave one feature on, Smart Inbox. I have a theory that alongside SaneBox, this feature may be of some use. It means that any email that isn’t automatically sorted by SaneBox may be sorted into separate groups like newsletters, pins, or seen emails. I think I’ll have to wait a few days to see how good this actually is.

Entry 8: After today, my email situation is basically the same, but with a small tweak:

Thursday, 28th January

Entry 9: This morning I decided to go all-in on Spark. So my iPhone, iPad, and Mac all have Spark set up. All with the minimal configuration.

Everything seems to be good, except that I’ve noticed I’m getting a ton of junk mail today. Maybe Thursday is a popular day to send email? Although this does seem to be only happening on my iCloud email. Maybe that’s because more people know about that email address, or because I have SaneBox on the G Suite account, I’m not sure. One thing is for sure, and that’s I’m looking forward to not dealing with this account in the future.

Entry 10: I listened to episode 62 of Cal Newport’s Deep Questions podcast where he answered questions regarding email. It mostly work scenarios, where you deal heavily with email, rather than a personal inbox. But I did come out with two things to think about:

Friday, 29th January

Entry 11: After settling making the change to having just two email addresses, I’m really contemplating making the switch to just the one very soon.

When I made the decision to forward all emails from a Gmail account to my G Suite account, I imagined I would need to deal with a lot of emails coming through that I needed to migrate. However, this hasn’t been the case. This could be the fact that SaneBox is dealing well with the spam, or maybe I just don’t get that through that account. Either way, I think I can mark that account as resolved.

The main issue I’m annoyed with at the moment is that my previous primary address (iCloud) just has so much rubbish going to it. I made the decision to not enable SaneBox for this account because I don’t want to manage two versions of every SaneBox folder. But I think the organisation and filtering benefits of SaneBox are what I need with this iCloud account. Because otherwise, it might be a bit unmanageable. Therefore, I expect I’ll end up setting my iCloud to forward all emails to my G Suite account.

Entry 12: I had a look through some more email apps on the App Store again, and I decided to try out Canary. Straight away I was presented with the option to upgrade to some kind of pro account, which I wasn’t expecting. I don’t mind paying for apps, but at least tell me why I should first.

After I found the trial button, I set up one of my email addresses in the app, and I was immediately turned off but the design. It seems like they’ve taken the native look of Mail but then tried to add their own functionality on top. Except it just looks a bit brutal to me. So I’ve already given up on that one.

Entry 13: I did end up forwarding my iCloud emails to my G Suite account, which means I finally have the one inbox to keep on top of. And also, I’ve got everything going through SaneBox, which I’m finding very helpful.

That means my email situation has changed even more:

Saturday, 30th January

Entry 14: After looking at loads more email apps on iOS, I can’t really find one that stands out as being better than Spark for my needs. Mainly because I don’t need that many “smart” features, I have SaneBox to do its magic via folders, and that’s it.

It led me to try to personalise Spark even more, and I think with what I’ve managed to do, I’ll be settling on Spark on all of my devices.

As I wrote before, I’ve already customised what folders appear in the sidebar and turned off a lot of features like snoozing, so it was already customised. But now I’ve had a look at swipe actions and also the toolbar.

For swipe actions, I have these four:

I think they’re a good fit, and will allow me to do nearly every common action via a swipe.

As for the toolbar, the items I have are pretty similar:

I think I’d prefer it if I could add more specific folder actions, rather than a single action that brings up a list every time. But I think I’m pretty happy with my client set up right now.

Entry 15: Since I’ve got all my emails going to the singular email address now (even if most are being forwarded from other accounts), and that account has SaneBox enabled, I decided to enable notifications for all of my emails.

I wouldn’t have done that before this experiment, because I would be getting too many notifications about emails I don’t care about. But now I know that most of the unimportant or junk email will be being sorted before arriving in my inbox, I feel a bit better about being notified about my emails.

Hopefully, I’ll only see important emails. But if I don’t, I know I can move them to various SaneBox folders to further train the service.

Entry 16: I just read Matt Birchler’s blog post, ‘How I’m Using Hey Email, Almost One Year Later’, and I think the way I’ve been using my email over the past few days is quite similar. Although, not using Hey.

So it’s good to see that how I deal with email, is probably possible to an extent via Hey. I’m not sure I’d use Hey now, because of the lock-in, and lack of custom domain support, but maybe in the future? Who knows.

Sunday, 31st January

Entry 17: There’s been no changes today, and to be honest I don’t see myself making any changes for a while. My solution is working well, and I’m pretty please.

I now have four places where my email goes:

Final Results

I’m pleased to say that I have achieved my goal of reducing the email I receive, only using the one account, having a level of automated sorting, and also having methods to permanently block annoying emails via SaneBox’s Black Hole feature.

I’m now using one G Suite email account, Spark as my client on all my devices, and SaneBox to keep everything working smoothly. I’m honestly surprised that I didn’t need a ton of extra services to achieve a good solution.

Now, I know this post is very long. And to be honest, I didn’t expect my entries to be as large as they are. Some of them could have probably been blog posts on their own. But I do think that having everything together and in order is much more valuable.

Even for myself, having this log to refer back to while doing this experiment has been helpful. That’s why I think it might also be helpful to others that are wondering about what to do with their email solution.

I could have simply written a post at the end of the experiment with my final decisions and how I ended up with a solution. But I think with that, a lot of thinking would have been missed. So not every decision would have been clear. It reminds me of having to include your working out" when doing maths at school, rather than just writing the answer.

I’ll probably end up doing more experiments like this in the future. It seems effective, and hopefully interesting to read.

Photo: (Yannik Mika via Unsplash)