Category Archives: Systemization

Doing Your Future Self a Favor

Not long ago I decided to transfer some of my retirements funds from one brokerage company to the other. For reasons that are too annoying and too complicated to get into, I had to do this manually through what’s known as an “indirect rollover”. The mechanics of it are simple: Brokerage #1 cashes out my current IRA (Individual Retirement Account) and sends me a check. I deposit that check into my normal bank account, then I call Brokerage #2 and tell them I want to take that exact amount of money and put it into an IRA with them.

If you do this correctly, the transfer happens tax-free. If you do it wrong, you can end up with a hefty tax bill. There are really only two rules to worry about: get the money into the new account within 60 days, and tell the IRS about it when you file your taxes. None of this is difficult, so long as Future Katrina does everything she needs to do. So I made sure to set her up for success.

I wasn’t too worried about doing the transfer in time since it would theoretically be done in about a week. However for added security and peace of mind I put two big reminders in all caps on my calendar for the day when my 60 day clock would run out, as well as 10 days before that so I’d have ample warning.

The thing I was more worried about was remembering to tell my tax accountant about the whole thing. Brokerage #1 said they would send me tax forms for the transfer, but I didn’t want to risk them getting lost in the shuffle or trying to remember the terminology to tell my tax accountant, especially because I was also transferring some other funds between the two companies that would be taxed differently. I have a folder where I keep all the tax-related forms and paperwork I receive throughout the year so it’s easy to find them all come tax time. I took out a sheet of paper, scribbled a big note to myself with all the key information about the transfers, and put it in that folder. When it’s time to collect my paperwork and send it to my accountant, there will be a big obvious message from Past Katrina ensuring that Future Katrina does the right thing.

There are two key components that made this work, one mental and one practical. The mental one is the practice of thinking ahead, of noticing when a task or project isn’t done and imagining what the future version of yourself will need. This mentality is what made me think to add reminders to my calendar and write a note for my taxes. The mental component will often manifest as worries before you are able to turn them into a plan.

The practical is the set of trusted systems to store all that forward thinking in. I already had a calendar that I referenced regularly, and a spot for tax papers to live. Without these things in place it would have been much harder to prepare for Future Katrina, because I wouldn’t know how to get messages to her. I wouldn’t be able to accurately picture the moment when she would need my help the most, or where she would look for that help. But because I trust these systems, I can trust them to carry the info along to the future and find Future Katrina at exactly the right moment. They are my time machine, and Tax Day Katrina is going to be very happy they were in place.


Six Small Things You Can Do When You Feel Helpless & Hopeless

As humans it is easy for us to get trapped in thought patterns. We develop relationships with the way things are and what we’re used to, and then the physical characteristics of our environment start to reenforce our behavior. Changing your environment, even if it means inviting temporary discomfort, can effect those though patterns.

Obviously rearranging your pen cup is not going to turn an election or end the pandemic. But changing the relationship with how we move through life, and especially with how we process incoming information via our devices, can change our thinking. It can make it easier for us to see new ideas and opportunity where there previously seemed to be none. It can remind us that certain things are still within our area of influence, even if many other things are not.

If you are currently dealing with feelings of overwhelm and anxiety over how much in life feels completely out of your control, try a few of these small things:

  1. Change the lock screen and background on your phone to something simple and soothing (perhaps just a solid color).
  2. Rearrange the icons on your phone’s home screen (either to make it more efficient or to make it prettier).
  3. Clear EVERYTHING off your desk, dust and wipe it all down, and put it back in a new arrangement (even a “sub-optimal” one).
  4. Turn your phone to grayscale, usually done through the Display Accessibility Settings (your phone is way less interesting in black and white).
  5. Turn off all the notifications, banners, and badges on your phone, except maybe for calls and texts. Turn them back on one at a time as you miss them (you won’t).
  6. Use the incognito mode on your browser today. You will have to manually log-in to every site you want to visit (Good).

NOTE: These are not invitations to avoid action and responsibilities. They are starting points if you are already doing exactly that. If you are currently paralyzed and doing nothing helpful for yourself or others, then going straight to good, useful, productive work might be impossible. And constantly chastising yourself for NOT doing that work will only ensure continued inaction. You might need to harness some small change to breakup the relationship you’re currently in with inaction. Good luck.

Six Unbalanced Areas of Your Life

As I try to navigate my way through living in a pandemic, I often feel like everything I need to do is of equal value, and therefore all of it is worth doing right now. I need to check my work email, but I also need to do my laundry, I need to exercise a little, I need to make myself lunch, I need to respond to the email from yesterday, I need to write my novel, I need to finish that TV series I started, etc. I allow all of these items to be equal in my mind, all of them feeling like they are what I should be doing and also what I should be putting off in favor of something else. And if I spend all day doing one type of thing and ignoring all others (or staying paralyzed and doing nothing), I feel terrible and wonder where my time went.

We’re all familiar with the idea of work/life balance, but that is not the only scale on which activity can be measured. Here are some other categories of distinction I’ve found useful to consider:

1. Complex vs Routine
How much fresh brain power do you need?

Complex: create a gardening plan, figure out a computer backups solution, write a novel, learn a new recipe, run a meeting

Routine: weed the yard, fix breakfast, read a book, do a puzzle, attend a meeting that could have been an email

2. Fun vs Practical
Is there a purpose beyond your own present happiness?

Fun: watch TV, play a video game, chat with friends or coworkers, bake something that isn’t good for you

Practical: reorganize the garage, clear out your email, sort through digital photos, meal prep for the week

3. Reactive vs Proactive
Are you doing this because you want to or because someone/something else is prompting you?

Reactive: return a phone call, buy a baby shower gift, sew a button back on a shirt, fix the lawn mower

Proactive: learn to quilt, start a new TV show, change a process in the office, build a shed

4. Maintain vs Accomplish
Once you do the work, will it be done or will you need to do it again (in the next five years)?

Maintain: practice an instrument, do the laundry, clean the kitchen, exercise, submit expense report

Complete: fix the dryer, create an emergency kit, buy a new desk, get all power moons in Mario Odyssey

5. Family vs Self
Would you still be doing this if you lived alone?

Family: cook for others, play with children, book appointment for a parent, have family game night, discuss partner’s work troubles

Self: work on a hobby, learn a new language, complain about your work troubles to a friend

6. Taxing vs Restorative
Over time, does it fill you up or wear you down?

Taxing: scroll social media, do physical labor, teach children to do anything, write a difficult email

Restorative: journal, take a bath, watch a movie with someone you love, clear off your desk


You’ll notice that no side of these scales is the “correct” side, or even the enjoyable or easy one. Each side is potentially negative if you spend too much time there. Spend too much time on accomplishment over maintenance and things will fall apart. Spend too much time on family over self and you might lose your sense of identity.

Every item exists on multiple scales at once. For example Family Game Night is routine, fun, proactive, maintenance, family, and either taxing or restorative depending on whether you’re introverted or extroverted (and how competitive your family is).

You probably keep a good balance in some of these areas already, and you probably have a suspicion about which one(s) you are routinely unbalanced in. If you’re unsure, take your current task list (the FULL one that includes home, work, longterm, etc) and try to sort the items into the two sides of one of these areas. Repeat until you find a category so unbalanced you can’t ignore it, and focus on adjusting the ratio for that one.

Depending on the person, balance doesn’t necessarily mean equal tasks on both sides. I’m a pretty ambitious and goal-oriented person, which means I can skew more towards practical over fun because oftentimes practical things are fun to me. But if I have 25 things on the Practical side and 2 on the Fun side, even I can admit I’ve gone too far.

Remember that balancing yourself out is not always about adding more to your plate – it may require things to be taken away. This is especially true right now as you are under so much stress. If you’re currently working, you might need to compensate for the kind of tasks you do at work. If your day job involves a lot of complex tasks, you might need to focus on more routine tasks in your home life to prevent exhaustion. If your job is mostly routine tasks you may want to look for complex things to ensure your days are fulfilling.

This is not about becoming hyper-productive while sheltering at home or “getting the most out of your quarantine”. It’s about keeping a sense of rhythm when other rhythms are lost. You would never insist that a friend spend all day sorting photos or all day pulling weeds. Remember to be at least that kind to yourself.

On New Year’s Resolutions

By now, more than 80% of New Year’s Resolutions have been abandoned. If yours was among them, here are some possible reasons why:

1) You didn’t actually want it

Perhaps you set a “should” resolution – something you think you should be doing that you don’t actually want for yourself. It’s very hard to achieve a goal you have no genuine interest in.

2) It was too ambitious

If you set your sights too high, you will very quickly find yourself failing to meet expectations and getting discouraged. Even if your big, ambitious goal is reasonable long-term, it may have been too much for one year.

3) It wasn’t challenging

When it comes to goals, too easy can be just as bad as too hard. If there’s no challenge to your goal it’s unlikely that the process will be very rewarding. Goals that are too easy to accomplish are also easy to put off, and easy to forget about.

4) You didn’t turn your goal into actions

If you set a goal to lose weight, but don’t plan any changes to your diet or activity levels, it will almost certainly not happen. You are what you do every day, which means that if you want to make a big change, there needs to be something you are doing every day or every week that is moving you in that direction.

5) You weren’t prepared for hurdles

A plan that only works if you never get sick or have a stressful work week or go on vacation is destined to fail. For a resolution to work there should be a plan or cushion to accommodate the unexpected (but ultimately foreseeable) events in life.


The thing about the New Year is that it’s arbitrary. Today is just as good a day to start a new habit as January 1st was. So if you’ve already abandoned your New Year’s Resolution, you still have a chance to start fresh. Figure out what went wrong last time, create a plan for how you’ll do things differently, and pick a new starting date.

How does tomorrow sound?

Your Mission:

If you’ve got a failed resolution you want to revive, ask yourself the following questions:

  1. Do I actually want this, or do I just think I’m supposed to want it?
  2. Is the goal I set for myself both realistic AND challenging?
  3. What is the thing I’m going to do either every day or every week that will get me to my goal?
  4. When and how will I check-in to see if I’m still on track?
  5. What will I do when I get off track?