Timing Blog

Starting Out as a Freelancer? Here Are the 5 Steps You Need to Do Now

2017-12-12T15:00:00+01:00

You just quit your job! Congratulations, and welcome to the freelancer club. Before you put on your pajamas and enjoy trashy TV, though, you need to set yourself up for success.

Fear. Excitement. More fear. A desire to eat a lot of carbs. The emotions you’re feeling if you’ve just handed in your notice are complex ones. And tempting though it might be, now isn’t the time to sit back and relax. Self-employment, small business ownership, or freelancing isn’t as simple as putting an ad in the paper and watching the money come in. Done right, freelancers are significantly happier. Done wrong, freelancing can burn you out, burn out your bank account, or both.

How do you avoid that, and make the learning process of becoming your own boss as easy as possible? Here are the first five steps you need to take. Not tomorrow, or next week, but now. Which brings us directly to the first point.

1. Commit All the Way

Setting yourself up as a freelancer often requires preparation. If you begin your business or freelancing career with the mindset that it’s just something to try, you will never succeed. Resist the urge to send out resumes, or look at other options. Right from day one, you should throw your Plan B out of the window. Having a backup will only hold you back from taking the risks you need to take in order to succeed. If you find yourself not fully committing to your plan, then ask yourself if it’s something you really want to do.

It’s like Yoda said, “Do. Or do not. There is no try.” Whether you’re a writer, a developer, a designer, or a Jedi in the making, actively deciding that you want to make it work no matter what life throws at you is the only way to ensure you won’t quit. No matter how rosy the future is looking at the moment, hard times will be coming. There’s no such thing as ‘getting lucky’ and landing that million dollar dream contract in week one, so get mentally prepared now to fight through.

2. Track Your Time, for the Sake of Your Work and Your Life

Do you remember that feeling before you left your job, when it would suddenly be 9p.m. on a Sunday — and you didn’t have a clue where the weekend had gone? That’s about to be your life. Going to get a cup of tea suddenly takes an hour because you became distracted by calling a friend, going for a walk, or opening Facebook.

If you invoice at an hourly rate, then you’ll probably be tracking already. If not, then it’s good to get into the habit of time tracking anyway, so you know how long you’ve been working on different projects. A common mistake when you leave the 9 to 5 is just that — you leave the 9 to 5. Suddenly you’re working everyday from 9a.m. till 1a.m., and you’re not sure where the time is going. If you feel like you’re burning out, read our article on how to rescue your work-life balance. Timing is the perfect app for finding out where you’re losing time and what your days really look like. It will also help tremendously with billing your hours.

3. Learn to Say No

One of the most valuable pieces of advice I was given when starting my own business was ‘try to only work with people you like.’ It’s been so useful to remember; I should get it tattooed on my forehead — or maybe just framed above my desk. Working with people you like, and saying no to those you don’t, will help cultivate long-term working relationships, make work a pleasure, _and _save you the stress and anxiety of people who micromanage, ask for things you can’t do, or cause you a headache in some of the numerous ways unique to bad clients. If you’re not sure what constitutes a bad client, don’t make the mistake of thinking this is normal treatment, but do some research on what you should expect.

Saying no from the beginning will save you a lot of time and stress in the long-run. Whether it’s working to a deadline you know you can’t meet, work you know isn’t your strength, or a client offering too little money. It’s extremely tempting to say yes to every offer when you’re just starting out, especially when rent and bills are looming. Start saying no without feeling the need to justify your reasons (it’s your business, after all), and you’ll be setting yourself up for a stress-free and profitable future.

4. Know Your Value and Your Limits

Imposter syndrome is something that afflicts most entrepreneurs at some stage, especially when you’re just starting out. Take time to read about what it is, and you’ll suddenly realize that the voices in your head telling you that you’re not good enough or that you’re a fraud, etc. are something perfectly normal — and definitely not voices you should be listening to. If you’ve started down this road, then it must be because you have a specific skill or are passionate about something, and that’s not insignificant. You’re not going to know everything at this stage, or ever.

Warren Buffet, the most successful investor in history, has one main piece of advice: “You are your own best asset.” Never sell yourself short or accept payment you know is less than you’re worth. Similar to knowing your value, knowing your limitations from the start is important. Trying to diversify too much, or too fast, shoots many freelancers in the foot early in their careers. It’s far better to pick one thing and specialize than to branch out into too many things, disappointing your clients and yourself.

5. Invest in the Right Tools and Software

Even if you’re just working from your laptop, start-up costs are never zero. The right software from the beginning can help set you up for a profitable future. From an effective time tracking app like Timing, to productivity software, bookkeeping tools, or writing tools, these all cost money and are an investment you shouldn’t be scared of making from the beginning. If you were setting yourself up as a masseuse, you wouldn’t buy a kitchen table to massage your clients on, so this isn’t the time to be cutting corners.

There’s also an element of fun and excitement to this stage, as it can help make the steps you’re taking feel real. If you’re even half as nerdy as I am, paying for a new type of software is exciting — I like learning all about the tips, tricks, and integrations involved, and if I’ve paid for it, I’m far more likely to dedicate the time to learning to use it.

Don’t let yourself rush into things; take time now to set yourself up properly using the steps above. It’s worth checking in regularly, too, since a lot of this advice isn’t valuable just at the start of your freelancing career but for years to come.

Have you downloaded your free Timing trial yet? It’s the fastest way to begin working on this list, and making sure you’re developing healthy habits that will last for years.

Burned Out? Improve Your Work-Life Balance with Timing

2017-12-05T12:00:00+01:00

Can something as simple as a time tracking application on your desktop change your mental, physical, and emotional health and well-being? Used creatively, yes! Here, we show you how.

If you were born in the 80s or 90s, you’re a millennial. And if you’re a millennial, then you’re probably stressed. It is official — we are the most stressed generation. This time of year doesn’t help either: The days are much shorter, meaning that by the time you look up from your laptop it’s dark, and the holiday season is approaching, pushing up your deadlines so you can take time off to be with your family. Don’t even get me started on the stress of being around your family, buying gifts, preparing for everything! By the time January comes, you need a holiday — but unfortunately, January is the worst month for mental health, so no chance of that, either…

If you’re feeling tired just reading this, then you’re definitely at least one step too close to burning out. It’s time to put off making excuses, and start looking after yourself by recalibrating your work-life balance. Using Timing, we’re going to show you exactly how you can do this. After all, without your health you have nothing — so why use a time-tracking tool that doesn’t help you stay in the best health possible, to do your best work possible?

Organise Your Work Into Projects

How’s your time management? If you’re a freelancer, you probably serve multiple clients at the same time. Remember that organisation isn’t the same as procrastination, and as tempting as it may be to deal with tasks as they come in, it’s going to result in some long working days as you struggle to keep on top of everything. Your clients don’t expect you to reply within two minutes, and if they do… they’re more stress than they’re worth!

So how do you organise things? To start with, empty your brain of everything you need to do today. How you do this is up to you — either an old-school planner/notes, or my personal favourite, a tool like OmniFocus — which is the best for Mac users — that allows you to dump out all those thoughts in your brain, organise them, and set up repeating tasks.

Once you know how much time you’re spending on things, set up projects in Timing to make sure you’re keeping to time. Properly organized, this will happen in the background while you work. Look at my day when I was planning this article:

You can see that I have everything color-coded, so I know I’m not working on any one client too long. To track your projects and make sure you’re not spending too long on any one client, set the timer before you start, and commit to only spending that long on it, like so:

By contrast, it’s also important to make sure that you’re not hopping to tasks too often — so no multitasking, however tempting it is. Multitasking is a quick way to raise your stress levels, as it releases cortisol in the brain. Commit to a task, but break larger, longer ones down if necessary.

Finally, plan in some non-work things to make sure you’re taking time away. What are your goals in your personal life? Again, take a look at my time log. You can see a workout in the morning, because running sets me up for the day, and a dog walk mid-afternoon. Both of these get me away from my desk, help me focus more, and release endorphins because they’re exercise — making sure I stay happy.

Use the Pomodoro Feature to Break Up Your Time

If you’re not familiar with it already, the Pomodoro method is a productivity technique designed to help you hyper focus by working in 25 minutes bursts. Work for 25 minutes, then take 5 minutes off. Repeat three times then take a longer break. It’s not hard — so if you have the habit of sitting down at your desk and not looking up till it’s dark, give it a try. To do so with Timing is simple.

Set yourself a project to work on manually, as we talked about in the previous section. Select ‘25 minutes’, which has Pomodoro next to it.
Once your 25 minutes is over, take a break… and time this too! Otherwise you’ll get distracted and start talking in the kitchen, we’ve all done it.
Repeat steps one and two. They’ll now be saved into Timing and will auto-fill, or suggest these projects, so it’s really no more complicated than having a tomato timer next to you on your desk, except that they’ll automatically be added to your day.

Plan Out Your Days the Night Before

Planning out your day the night before is a real stress buster, and it’s vital if you’re someone who struggles to sleep. While Timing itself doesn’t have a functionality to help you do this, it’s fantastic when used in conjunction with something else — like Omnifocus — to optimize your day. Take a look at your day in review. Let’s go back to a screenshot of mine.

During my day above, I got to bed early enough — but I work best in the mornings, so starting earlier would have helped me do more. By being honest with yourself about where you’re falling down, not only can you plan more efficiently, but also know where you can maximise your time during the day.

Seeing your whole day in review is amazing for helping you understand your stress levels. You just worked? Plan some more downtime in tomorrow! Didn’t work enough? Make sure you’re maximising your time!

Make Sure You Log Your Time Away From Your Desk

On your menu, you have the option for Timing to ask you what you were up to whenever you return to your desk. This isn’t just nosiness, honest. Keep the box checked to keep you accountable, and log everything you did while you were gone.

Track anything you’re doing work related, whether it be phone-calls, meetings, iPad work, or anything offline. Are you checking notifications or replying to emails on your phone when you’re out? Stop it! By tracking your time away from your desk, you’ll see how much you’re really working. Track anything you’re doing that isn’t work, but isn’t enjoyable, too. Household chores, paying bills, running errands… they’re all part of our daily life, but they’re not hobbies or time for yourself.

Finally, track your leisure time. To be happy, we’re supposed to have 7 hours a day. If that sounds like a lot to you, you’re definitely not getting enough downtime… meaning you should definitely be tracking it to find where you can get more.

Harness Your Most Productive Hours

If you’re freelancing, then you have far more flexibility to create a schedule which works for your body. Timing means that you can use the overview page to see your most productive hours and days. If you have a lull time where you’re clearly not productive — 11am or after lunch for many people — then use it to do something fun and for you instead.

Unlike the 9-5, my day is broken up. I walk the dog before it gets dark, and I also know that if I start early, then I need a break to exercise at around 11am. As you can see from the screenshot, I’m less productive from 1-3pm, so I avoid scheduling any important work at this time. Knowing that I’m less productive means it’s a great time to make use of daylight hours, without feeling bad about not working.This is me personalising my working day for efficiency. It also looks like I’m more productive on Wednesdays and Fridays, so if I’m meeting a friend or going out — I make sure to avoid scheduling anything on those days. Don’t just guess when you are and aren’t productive — use Timing and restructure your days accordingly, meaning you can maximise both your work and play.

Play With Your Productivity Ratings

Why should only your paid work be considered productive? What are your other goals? To have balance in your life, you need to be working towards more achievements than just ones for your business. Timing automatically sets 50% productivity to all your projects, so take some time going through and working manually editing it to suit you.

If you want to get fitter, set time exercising to 100% productivity. If you want to spend more time cooking and eating, to get into a routine, then set that high. In contrast, if you want to spend less time on social media, then set it to 0% productivity. Add keywords, so that every time you go on Twitter or Facebook Timing logs you as being unproductive.

No one is impervious to burnout. No matter how much we love what we do, we’re all susceptible to it, especially at this time of year when we’re not getting enough sun. If you’re feeling tired, anxious, stressed, or even just like you’re not being productive enough, take some time to put the ideas above into action. When we’re expected to be available and switched on to work 24/7, switching off and taking time for yourself can be hard, and hard to justify when you’re feeling the stresses building up. Through careful planning, time management, and habit building, you’ll see your productivity, energy, and happiness levels start to rise. No more excuses, it’s time to start getting your work-life balance into order!

If you haven’t already done so, download a trial of Timing here and start putting this advice into action immediately.

Track your writing time with Ulysses and Timing — your chance to win a Ulysses subscription!

2017-11-01T15:30:00+01:00

Do you write? Whether you’re a professional writer or just enjoy writing as a hobby in your spare time — if you write a lot, you should have a look at Ulysses, the writing app for Mac, iPhone and iPad.

The app is popular among freelance writers, bloggers and novelists alike and has even been awarded with an Apple Design Award in 2016!

And with Ulysses 12 and Timing 2.2.1, we joined forces with the Ulysses team for much tighter integration between the apps, allowing for detailed tracking of your writing time.

Read on for more details on Ulysses and the integration, as well as the chance to win one of five one-year subscriptions for Ulysses!

Ulysses is both a powerful tool for managing your texts and a focused editor that lets you concentrate on getting your words down. You work in a beautiful, distraction-free environment. Ulysses’ library lets you organize your writing according to your needs, be it a novel, a collection of articles, or a diary. You can organize your texts with filters and keywords, you can set yourself writing goals, and much more.

Ulysses’ export function is very capable — the app lets you easily export to a host of standard formats such DOCX, PDF and ePUB. Also, you can upload your texts directly to a WordPress blog complete with images and tags with just a few clicks.

Ulysses works on Mac, iPhone, and iPad and syncs seamlessly. That way, you can have all your writings always at hand.

As you can imagine, it’s possible to spend a lot of time in Ulysses. Thanks to the integration with Timing, you can find out how exactly that time was distributed across all your writing projects.

Ulysses lets you organize your writing projects into hierarchical groups; the writing itself is done on so-called sheets (sheets are somehow equivalent to documents) inside those groups. And with Ulysses 12 and Timing 2.2.1, we are bringing sheet-level automatic time tracking to Ulysses.

From now on, Timing will show you exactly how much time you spent in each Ulysses sheet as well as the groups that enclose it. That lets you easily get an overview of how much time you spent working on a particular chapter or even the whole book!

Imagine you are working on a novel and have set up the project similar to David Hewson’s group structure:

You’ve got a top-level group called “My Writing Project”, which contains two sub-groups “Manuscript” and “Management”. The first group contains your actual writing, whereas the second group contains things like notes or descriptions of characters.

Apart from these groups, you might have other writings in Ulysses, such as reports, shopping lists or poetry. When tracking time, you don’t want all of that to count towards the same “time bucket”. What’s more, you may want to track the actual writing and your notes separately. Fortunately, Timing can do all this for you. Open up Timing and switch to the “Review” section, where you can create your own projects. For instance, I’ve set up a simple “Writing Project” here:

It has three subgroups: “Web Research”, “Writing” and “Character Descriptions”. I’d like to track my usage of Safari into “Web Research”, working in my Manuscript group into “Writing” and working in the “Characters” group into “Character Descriptions”.

You can automatically categorize activities by creating rules for them. For instance, if you want to consider all surfing activities in Safari as “Web Research”, select the “All Activities” project, hold the ⌥ (alt/option) key and drag Safari from the Applications card onto “Web Research”. Now, all surfing in Safari will automatically be counted towards that project.

Similarly, if you are editing a sheet in Ulysses like this:

That time will be tracked in Timing as “iCloud ▸ My Writing Project ▸ Manuscript ▸ The Sassafras”. So, to assign all writing time in the “Manuscript” group to the “Writing” project, simply drag the “Manuscript” entry from the “Paths” card and drag it (while holding the ⌥ key) onto “Writing”:

Finally, you can do the same for Character Descriptions by dragging the path “Characters” on the activity. Please note that for the paths to show up in Timing, you first need to create and open at least one sheet in the groups to let Timing pick up the paths.

From now on, every time you work in these groups, Timing will track the activity and add it to your projects, helping you find out how much time you spent writing in a group or on a sheet. That way, you know exactly how much time you spent writing that book or even a particular chapter!

Get Ulysses

Ulysses can be downloaded for free on the App Store and the Mac App Store. After a 14-day trial period, a subscription is required to unlock the app on all devices. The subscription costs $4.99 monthly or $39.99 yearly. Students can use Ulysses at $11.99 per six months.

In addition, both Ulysses and Timing are part of Setapp, the service that gives you access than more than 100 apps for just $9.99 per month! You can sign up today to get access to all these apps (and others like Aeon Timeline, which also integrates with Ulysses) immediately.

Your chance: Win a Ulysses subscription!

In addition to the new integration between Timing and Ulysses, we have partnered with the Ulysses team to give away a total of five one-year subscriptions for Ulysses!
~~Simply perform one or more of the actions below before Friday, Nov 10th, 2017, to enter into the giveaway.~~
The giveaway has ended now. Congratulations to the winners:

Stephen S
Jesse B
Sarah K
Cristóbal T
Charlotte H

How to accept payments for your digital products — without losing your mind about taxes 💵 🖥

2017-10-27T13:00:00+02:00

In the latest episode of Core Intuition, Daniel Jalkut talks about switching from PayPal to Stripe as the payment method for his Mac app MarsEdit. This sparked a discussion on the corresponding Slack team about the pros and cons of different ways to handle selling your digital products.

European VAT rules, accounting and other distractions make this harder than you think!

In this article, I will outline the common payment options for digital products and their individual advantages and disadvantages. This is from the perspective of a Mac developer, but apart from the licensing aspect, it applies to all other digital products as well, including SaaS subscriptions and online courses.

Note that I am neither a lawyer nor an accountant; these are just my personal recommendations.

Having people send you cash or checks in the mail

Fees: None (I guess)

This used to be the state of the art in accepting payments — in 1992.
In 2017, it is the fastest way to kill your business.

Advantages

That warm, fuzzy feeling when someone really goes through the hassle of putting cash in an envelope with postage and going to the post office, just to buy your software.
No third-party dependencies (other than your local mail provider).

Disadvantages

Everything else. Let’s move on.

Having people send you money via PayPal or Stripe

Fees: 2.9 % + 30 ¢/transaction (Stripe, PayPal, Braintree)

You could either just have a PayPal “send me money” link on your website, or create a payment form with an automated process that delivers your license code.

This might be the option that naturally comes to mind, but keep in mind that you are still responsible for creating proper invoices and charging (and deducting) VAT in countries that charge it, including about all EU countries — which also charge varying VAT rates per country.

If you are based in the US, you might get away with ignoring the EU’s VAT rules altogether, but I don’t recommend that. You would be in good company there — looks like Panic and The Omni Group have just that approach — but I still don’t recommend it. (I’m German. We really like to avoid risks.)

Advantages

The cheapest way to accept payments online.
Just one dependency that is also easy to switch out in case you need to.

Disadvantages

You are responsible for proper handling of VAT, which is a mess. Read this article if you’d like to learn more.
You’d also be responsible for creating proper invoices and accounting for your payments. You might get away in just booking the lump sums sent to you every month by Strip/Paypal/Braintree, but in some cases you might need to have every individual transaction in your books. If unsure, talk to an accountant.
You also need to implement the whole licensing system yourself. This can be a lot of work. (See the bottom of the article for some pointers on how to deal with that.)
In the case of PayPal: You have to deal with PayPal, which is a terrible company (Source, Source).

Having people send you money via Stripe, but letting someone else deal with that whole VAT mess

Fees: 2.9 % + 30 ¢/transaction (Stripe) plus $31/month (Taxamo), $31/month (Octobat) or €29/month (Quaderno)

If you ask me, this is a much better approach. VAT is such a complex matter that it’s really hard to get right, and as with all taxes it is something you don’t want to mess up. With some services (such as Quaderno), you might also have some of the accounting and invoicing done for you.

Advantages

Much less work in terms of VAT/invoicing/accounting.

Disadvantages

You probably still need to sign up for an EU VAT ID and file your VATMOSS return yourself. (Not 100% sure about that, though.)
You now need to manage two services.
Slightly more expensive.
Still have to deal with licensing yourself. (Again, see the bottom of the article for some pointers on how to deal with that.)

Having a reseller handle payments, invoicing and VAT for you — but with your own licensing system

Fees: 5 % + 50 ¢/transaction (Paddle, affiliate link), slightly more with FastSpring, $10/month plus 3.5 % + 30 ¢/transaction (Gumroad)

In this case, your reseller acts as your Merchant of Record. This means that they are the actual business taking your customers payment, and thus responsible for creating a proper invoice, dealing with VAT, and so on. At the end of the month, you just get a nice lump sum transferred into your bank account, which also makes your accounting easier.

This is actually the option I use: I use Paddle, which lets me avoid dealing with all the payment stuff, and combine it with a completely homegrown licensing system. That way, I retain full flexibility in terms of pricing, discounts and licensing. I can offer paid upgrades, limited-time licenses and whatever else the business requires. And in case there’s a problem with one reseller, it is still fairly easy to switch to another one as just the payment-handling part (but not the licensing) is affected.

To be honest, Paddle isn’t terrific, either. Their checkout process looks nice and is very straightforward, but they have been slow in implementing new features and there are a few edge cases I’d like to have handled differently. I’d say they definitely are the service that sucks the least, though ;-) FastSpring is fairly similar to their service, though, but costs a bit more. (Their pricing page no longer shows their pricing, but it used to be around either 8.9 % or 5.9 % + 95 ¢/transaction).

Gumroad might look like the cheapest option, but keep in mind that their service was not built for selling Mac apps or subscriptions. So while it might be possible to make these work with Gumroad, you’ll likely have to jump through more hoops than with Paddle or FastSpring to accomplish the same goals.

Advantages

VAT, invoicing, accounting all done for you.
You are still able to switch resellers, as you are not locked into a particular licensing system.

Disadvantages

Still more expensive, but I’d say it’s worth it.
Still have to deal with licensing yourself. (See below for tips…)

Using a reseller and their existing licensing system

Fees: Same as above — 5 % + 50 ¢ (Paddle)

This is the most convenient option, most similar to the Mac App Store. Just plug in an SDK and have that deal with all payment and licensing issues.

For example, the reseller Paddle also offers an SDK to handle licensing for you. To be honest, I tried to use their system but found their licensing system way too inflexible for my needs (unless you replace most parts with your own, custom solution, in which case you could just build the whole thing yourself).

However, you could also use a third-party licensing system such as DevMate. In fact, DevMate was recently acquired by Paddle. Given that DevMate was originally developed by the great people at MacPaw, makers of the Setapp service), I would imagine their system to be in much better shape than the original Paddle SDK.

However, in either case you are locked fairly tightly to a specific reseller when you use their licensing system. DevMate might still be compatible with FastSpring, but I would still be a bit worried in case you’d ever want to switch resellers or migrate to a different licensing system.

Advantages

Very easy and worry-free, almost drop-in.
VAT, invoicing, accounting all done for you.
No need to worry about licensing, either.

Disadvantages

Fairly tight lock-in. Switching to a different reseller (and a different licensing system) would be painful.

These are the payment options that I could think of. I went with a combination of Paddle for payments, invoicing and VAT handling plus my own, homegrown, licensing system.

For most Mac developers, it would be wise to combine a reseller such as Paddle or FastSpring with an open source licensing system such as CocoaFob (also see my Python-based CocoaFob license generator and server) or Aquatic Prime. Both are fairly easy to integrate. This lets you avoid worrying about all the payment problems, while retaining full control of the licensing system. (Alternatively, my friend Christian Tietze wrote a book on how to sell your Mac app with FastSpring.)

What payment and licensing systems do you use? Are there any points I missed? Let me know with a tweet to @daniel_a_a or an email to daniel at timingapp.com!

What we learned evolving an App through 20 (!) Alphas and 10 Betas

2017-06-12T10:00:00+02:00

One month ago (on May 9th, 2017), Timing 2 was released. Time for some navel-gazing!

More seriously, development started in April 2016 and the app’s interface changed quite a bit over the course of those 13 months:

This article illustrates how an app’s UI evolves during development, and highlights some subtle but important changes.

If you aren’t interested in the evolution of the app, scroll to the end of the article for a side-by-side comparison and a summary of some little changes that had a big impact!

Alpha 1 (July 5th, 2016)

Timing 2’s initial concept revolved around “smartly” recognizing blocks of uninterrupted time and displaying them as separate groups. While the first alpha already recognized the blocks correctly (as illustrated by the timeline), the activity list was way too noisy to be even remotely useful.

Also, note how rough the interface looks — but that’s expected for an app in the prototype stage 😉

The alpha also included a mode that grouped by application and file instead of by time — somewhat more useful, but it wasn’t even the default:

As you can see, even Timing’s rule editor is already present, but still very simple.

Alpha 5 (August 24th, 2016)

This version already had cards that group activities by different criteria (see here for an explanation). This turned out to be much more useful in than the grouping by time or by duration.

Also note the AutoGroup button in the toolbar. That feature would try to detect blocks of time, letting users quickly create tasks for these blocks. While the idea is very useful (and still present in the final version), having to go through these blocks one-by-one was cumbersome. Plus, the button in the toolbar didn’t make for a very discoverable feature.

Alpha 7 (October 19th, 2016)

The AutoGroup button was scrapped and replaced with permanent suggestions in the timeline:

These are more accessible and easier to use, as one can pick and choose individual suggestions to use rather than having to go through all blocks one-by-one.

Notice the new tab bar that leads to the ugliest dashboard ever:

Alpha 7 also marked the introduction of a (still very bland) onboarding tutorial:

Alpha 10 (November 7th, 2016)

Replaced the ugly dashboard with a different — but still ugly — one:

Around this time we hired Eduardo Santos to help design the app. You can already notice the first effects of his work in the much-improved timeline 😉

Alpha 13 (November 17th, 2016)

Eduardo’s work is becoming much more noticeable, for example in the improved tab bar and task editor.

Alpha 17 (December 6, 2016)

We have a proper dashboard! Still ugly, but getting there.

Alpha 19 (December 16, 2016)

Much better! This dashboard is actually surprisingly close to the final version. It even featured a responsive layout:

The Review screen has made some progress as well:

Notice how there are scrollable lists inside a scrollable container. That turned out to be a terrible idea — it makes scrolling incredibly frustrating. (I take full responsibility for that…)

It was finally time for the…

Beta 1 (Jan 12, 2017)

At this point, we felt confident enough to circulate Timing 2 to a wider audience — even the project editor was fairly close to the final version already.

Until May, nine more betas followed (including additional features, such as manual time tracking, a reports screen, AppleScript support), but the overall design of the app changed surprisingly little from this point.

Timeline changes in detail

At first glance, the timeline hasn’t changed much over the course of the project:

Yet what a difference these changes make!

The task suggestions make it much easier to assign whole blocks of time at once.
Coalescing short activities makes the timeline much less noisy and easier to comprehend. (We could probably coalesce even more aggressively.)
The app icons on the timeline make it easier to see what a particular timeframe was about (note e.g. the block of development between 10:00 and 11:00).
The row labels, combined with improved typography and colors, make the timeline appear much more friendly.

Conclusion

We could have stuck with our initial approaches for the activity list and automatic grouping and moved on. But the app would have been much worse for it. Luckily, we were able to step back and try different approaches that ended up working much better:

We switched from grouping the activity list by time blocks to grouping it by four different criteria instead. This made the activity list(s) much easier to parse and lets you quickly get an overview where your time went, without having to dive in.
The initial version of automatic grouping had you go through each block of time one by one, which was a pain to use. The modified version (task suggestions on the timeline) works much better — it lets you review all suggestions at once and pick the ones you need.

As you see, there can be quite a difference between the initial prototype of an app and the final product! Before committing to a particular approach, consider doing some user tests on your prototypes to validate whether your solution is actually solving a user problem or not.

To recap:

Your app’s design might change significantly through several iterations. Embrace that.
Be willing to kill your darlings — some approaches might simply not work.
A good idea itself isn’t enough. Presentation and execution make a big difference.
Test early, test often.
Consider building a solid technical base before polishing the interface. Having this base in place let us implement and iterate on Eduardo‘s designs quickly.
Your first prototype will look shitty. Keep going!