Marriage, Taxes, and OmniFocus

Wed 10 February 2016

I don't remember when I first heard of the term, "Marriage Tax". It was probably during some election cycle and someone running for office was blaming somebody else for something. Nevertheless, the idea that couples paid more in taxes when filing a joint tax return than when filing as separate individuals stayed with me.

When tax season rolled around last year, I assumed that filing jointly with my wife would be more expensive than filing separate returns. I was wrong.

The Marriage Bonus

In general in the United States, two people filing as a married couple will save money versus if they filed as individuals. This has been happily known as the “marriage bonus”.

(Of course, everyone’s situation varies. There are many scenarios in which couples end up paying more. So please don’t take anything in this article as tax advice. Consult your accountant.)

My wife’s accountant suggested that my wife and I file jointly; my own accountant concurred. So we did and we saved a little money in the filing. However, this did not come without cost.

Bonus Work

Prior to getting married, I had to handle two tax filings every year. In addition to that, I now have to also make sure all of my wife’s tax papers are organized in order to file our joint return. But even though it’s not a trivial thing, I’m handling the additional paperwork easily enough with the help of OmniFocus.

Tax-related deadlines are incredibly easy to forget. The paperwork can be voluminous. OmniFocus makes it easy to make sure that the proper reminders come up when needed.

OmniFocus for Taxes

In my last post, I mentioned that I have a task named Taxes in OmniFocus. There’s slightly more to it than that.

I actually have two tasks called ”Taxes”. The first one resides in my company’s OmniFocus project, under “Finances”. The second is in my “Home” project, also under a task named “Finances”.

Taxes for the Company

The company task is used for tracking the steps I need to file my company’s returns:

OmniFocus: Tax Steps

Each step in the process is a different subtask. As I do each item, I check it off the list. Once everything is done, I check off the main list, and the entire list is automatically recreated for the next year.

OmniFocus: Repeat Annually

This is easily done by setting the option in the parent, "Corp Taxes", task.

Taxes for the Home

The home task is used to track the steps for filing our personal taxes. I also use it to track the different forms we collect from different financial institutions. One set of forms is grouped under my name. Another set is grouped under my wife’s.

OmniFocus: Collect Forms

These are also set to repeat every year in the same manner. Tax forms for one year are very often used again in the next. This is an easy way to make sure I don’t miss any of them.

Taxes, Simplified

Getting married resulted in a slightly more complicated tax season for me. But using my OmniFocus system helped me manage the transition. It's a pretty simple system, but it's incredibly helpful. I can feel fairly relaxed in knowing that I'll remember to take care of my tax paperwork when they need to be done.

Speaking of which, I'm in the middle of tax prep busyness right now. Hopefully you find this helpful in some way to manage yours. Let me know via twitter or email! (at

stay diligent

OmniFocus for Home Management

Tue 02 February 2016

Chores – a necessary evil. As a kid, I would do them when my mom told me. Living with roommates in college, I’d do them when I got around to it (and if nobody else had gotten to it first). It wasn’t until I had lived alone for a couple of years and found two-foot dust bunnies living under my bed did I realize how important it is to take care of chores regularly.

When dishes aren’t washed, they pile up. When the trash isn’t taken out, it starts to smell. When plants aren’t watered, they die. And I already told you what happens when you don’t vacuum.

Growing Up

So basically, I grew up and started to take care of business at home. But all this was still pretty simple when I lived alone. For the most part, I’d just wing it. Every once in a while, I’d forget to do something, but it was no big deal.

Today, I live in a bigger home, with one other person. Shared lives means shared responsibilities and a shared calendar. This means that winging it is no longer sufficient. So I took a page out of my work life and set up a system for organizing home chores with OmniFocus.


OmniFocus (OF) is a personal task manager created by the Omni Group as part of their productivity suite of apps. I’ve been using this app for about four– to five years now (I can’t remember exactly how long). It’s the best thing I’ve found so far for keeping me on track at doing things that need to get done.

This app is pretty feature heavy, so it may be a bit of overkill to use just for the home. But if you’re already using it for work anyway, adding home management is a no-brainer. If you’re in the market for a task management app, it’s definitely worth taking a look.

For the home, I use OF to schedule all the routine maintenance work I mentioned above. In addition to that, I also use it to make sure taxes get done, bills get paid, doctors are visited, etc. I’d find it pretty difficult to get through a month without it.

How I OmniFocus at Home

Two things about OF I find make it useful for home task management:

  • a hierarchical project structure
  • scheduled, repeating tasks

The Task Hierarchy

If you’re at the point of scheduling your chores at home just to get them done, then you’re already probably juggling a lot of different things coming from multiple directions. (If not, then maybe take a look at some simpler alternatives below.)

OmniFocus lets you organize these many tasks into a multi-level hierarchy. This allows you to place related tasks together and manage them as a group (as well as individually).

OmniFocus Task Hierarchy

The top level in OF is known as a “project”. So I created a project called Home where I placed my home management related tasks. Under this project, I have various high-level groupings of things that need to get done:

  • Home Office
  • Home Maintenance
  • Finances
  • Automobiles
  • Travel
  • etc. (you get the picture)

For work related tasks, I have completely separate projects. (For instance, tasks for this blog are under a project named Diligent.) This keeps a clear separation in place.

For additional clarity, you can add as many layers as you want underneath the project. My Finances task, for example, has sub-items like Bills and Taxes. In turn, Taxes has 2015, 2016, etc.

The ability to organize tasks in this fashion, something missing from simpler “to-do” list apps, makes OF invaluable to me.

Scheduled and Repeating Tasks

Back when I lived in an apartment by the beach, (quick visual aside...

Beach Sunset

...okay, I'm back) one perk I had but didn’t realize at the time was the dumpster behind the building. Ask me what day trash pickup was – I had no clue. I still don’t. Anytime I had to take out the trash, I just brought it out back, no problem.

Today, I live in the suburbs. It’s a wonderful house with a great garden in the back, but there’s a schedule to picking up the trash. They come by every Wednesday, so by Tuesday evening, I need to make sure the bins are out front, ready for pickup.

Simple Tasks

This is where OF’s scheduling and repetition features come in handy. I have a task set to come up every Tuesday afternoon reminding me to take the bins out. For Wednesday evenings, I have another task reminding me to bring the bins back in.

Remembering to do this every week seems like a pretty simple thing, and it is. But forgetting to do it just once (and having to wait a whole extra week to get rid of trash) makes you appreciate having a system to remind you.

But of course, it’s not just the trash. I used to be a plant-killer. No longer – I have a weekly reminder to water the plants. I hate vaccuming, but when that reminder comes up, I at least think about doing it.

Infrequent and Important Tasks

Then there are the things that are truly easy to forget: tasks that come up much less frequently, yet are even more important.

  • Bills need to be paid monthly – I have a checklist for the important ones that shouldn’t be missed.
  • Regular dentist cleanings are now a thing (every six months).

And annual tasks won’t be forgotten either – we have an annual airconditioner checkup scheduled soon and the rowing machine will need a new water purified tablet in a few months.

These are all things that I pop into OmniFocus, then forget about until it reminds me.

It’s pretty great. If you need a task manager, you should try it out.

OmniFocus Alternatives

So that’s how I manage at home with OmniFocus. But if you don’t need something that powerful yet, then you can probably get by with these simpler apps:


Reminders comes built into the iPhone, the iPad, and Macs, so there’s no additional cost to using it. You can schedule it to repeat on a regular basis, but that’s pretty much it. Organizing tasks is limited to creating separate “cards” for different groups of tasks.

This works for really simple things, but any level of complexity at all makes the app unwieldy.


There are many other third party task-management apps on the app store. I highlight Wunderlist here because it is one that I actually use in addition to OmniFocus.

This app is a step above the stock Reminders app. In addition to scheduled and repeating tasks, it also gives you some basic organization capabilities (like folders and subtasks). It also has features for collaborating with other people (something I’ll write about in a future post).

Wunderlist isn’t for heavy-duty task management in the same way OmniFocus is, but it excels at what it does at a lesser cost.

A System

OmniFocus is just one part of the system I’m using to manage our home and my business. I’ll be writing much more about this and other topics on this blog.

You should let me know on twitter or tell me by email at what you think or if you have any questions.

Thanks for reading!

Weekly Post Checkmark

Introducing: The Diligent

Mon 25 January 2016

I’ve written a couple of posts now, I guess it’s time for an introduction. I’ll write a little bit about these two businesses I’ve mentioned and a little bit about we, the people behind them.


I’m Anthony, and I do software. By that, I mean I work as a software consultant to clients. My business is structured as a one-person S-corporation that I established in 2007.

I'm also an aspiring software product developer. I’d like to either create software that I can sell or create a software-based service. The current focus of my work is building out some ideas and testing them in the marketplace.


My wife prefers not to be named directly, so for the purposes of this blog, she’ll be known as “M”.

M basically manages operations for her family business. She is part of the third generation of family members to run a food service establishment that her grandparents founded over fifty (!) years ago.

Their business is old-school in many ways, the most important of which is their close relationship with many of their customers. They also happen to be old-school in their use of technology, which is very minimal. I’ve never met a more dedicated bunch, and I’m proud just to be associated with them.


We’ve been married for about year and a half now. From a personal standpoint, things have never been better. I can't imagine life without M anymore.

At the same time, that first year brought on other major changes to our life. We both run our businesses out of our home and we both have non-traditional working hours. Bringing those into the same household created some unique challenges.

After a bit of a rough start, we managed to put things in place and got a rhythm going. By the end of the year, we were ready with a better plan for tackling the new one.

The Diligent

This blog is the story of how we are taking care of business, at home and from the home. We’re working to build our respective companies, and at the same time build a family together.

Though our two businesses are polar opposites in multiple ways, there are two things they require in common from us: hard work and smart work. We have tools and techniques from the tech and business worlds that help us get this work done. Now, we are using them to help manage how our work and home lives intertwine.

I’ll write about those tools and techniques here, and hope that some may find them helpful!

I know I speak for M when I say that I hope we live up to this blog’s name,

– the diligent.

Our Annual Retreat

Sun 17 January 2016

Things get busy. Coordinating two sets of business calendars, family obligations, and a shared social calendar can get pretty crazy. This year, we’re grabbing the bull by the horns.

The Year Past

We started our first year of marriage, our first sharing a home, believing we could continue our lives from where we left off as separate single people. The first few months were fine, but when a couple of unexpected things came up (family emergencies, business emergencies, health issues, etc.), things started getting away from us.

However, we were able to manage. It’s not the most romantic thing, but we used a few tools that people normally only use at work to get things under control at home. Yes – we started using shared calendars, to-do lists, and even regular “meetings” (separate from date night, of course) to keep things on track.

Those tools helped us get out of the hole in which we found ourselves. I’ll blog more about those tools in future posts. But our first priority this year is to avoid the hole altogether.

The Year Ahead

We decided to take stock and plan things out before the new year revved up. To achieve this, we scheduled time away from both of our families to conduct a retreat.

A Retreat

After we got back from our first annual Mammoth Mountain Christmas in January, we booked a room in a hotel on the other side of town. There, the two of us spent a night making plans for the year, discussing our budget, and telling each other what we hoped to accomplish.

Again, this doesn’t sound romantic at all! But I think doing this on a regular basis can do nothing but help our marriage. Our discussions brought out truths about each other’s goals that we could only have assumed, possibly never even have guessed.

When we drove back home the next afternoon, we both agreed that it was time and money well spent. We had discussed and planned for things like:

  • how to stay healthy (I was working too much, not exercising enough)
  • combining our finances into one budget
  • aspirations for her business
  • aspirations for mine
  • family and friends

There were tough moments about some topics, but those were best broached when we did, before they grew into large scale problems. I’m glad we addressed them.

We now have a clear view of how our year should progress, if everything goes to plan. Of course, plans are meant to be broken. But now, we have a reference for getting back on course. We’re now ready for the year and to see what we can accomplish.

The Years Ahead

This year, we’ve established two new traditions that I hope continue into the future and help us form a strong family and build strong businesses.

We have an annual January trip with my family to go along with the annual September trip her family has always taken. We also initiated a separate retreat, for just the two of us, to help us take stock and plan ahead.

It’s just the beginning, but we have to start somewhere. I’m looking forward to many more years of this!

Christmas in January

Sat 09 January 2016

We celebrated Christmas in the mountains last week, the first week of January. My wife and I drove up to Mammoth Lakes to meet my mom, sisters, and other family for a few days of bonding time in a mountain retreat. We exchanged presents, some people got on the slopes, we enjoyed the heavy snowfall, and everyone participated in a potluck night.

Not everything went according to plan, but we all had a great time anyway! I hope an annual trip becomes a family tradition.

A Snowy Road to Mammoth

The Road to Mammoth

Why January?

But why did we celebrate two weeks later than normal? We did it for some of the same reasons I started this blog.

My wife and I got married about a year and a half ago. Aside from the wedding being a great party, it also marked the beginning of major changes to our lives. Although we had practically been living together for over a year, the reality of combining the households of two independent people still required a lot of work, foresight, and patience on both our parts.

Complicating matters further, each of our households came attached to home-based small businesses requiring additional space in our home and time in our lives.

The Dilemma

One high priority scheduling task (as it is in many homes) is the holiday season. What makes it more difficult for us is that my wife’s highly seasonal family business peaks during the weeks of Christmas and New Year’s Eve. It’s such a busy time that they recruit the help of family and friends to help out every year.

Before I married my wife, I would make an annual Christmas pilgrimage from my home in Southern California to the San Francisco Bay Area – where I grew up and most of my family still lives. Today, that old plan is out of the question: my wife would be unable to accompany me, and I would have to cut my trip short.

The Compromise

So a little bit of planning and compromise led us to our new plan: Christmas in January! With the approval of my sisters and my mom, we decided to celebrate with them a couple of weeks later. To make it more exciting, we would travel to a different locale. This way, my wife could fully concentrate on her business during the busy season and I would be able to help out if needed. Afterwards, we would spend quality, non-rushed, time with my family. Getting a white, snowy Christmas in the California mountains was just icing on the cake!

This Blog

So that’s the story of our Christmas this year. But merging our lives and businesses together has required lots of other little adjustments, tools, and tricks. It is an ongoing affair.

That’s what I plan to write about on this site.

More and more people are working from home these days. And more and more couples are running side businesses for fun, ambition, or just to make ends meet. Hopefully, some of the things I write about can be of use to someone else.

See you next time!

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