Getting busy and being social for the socially awkward

Dann's busy calendar

A few years ago I found myself out of a long-term relationship and suddenly had nothing but free time. As a homebody, both in and out of relationships, this was fantastic. I’d take the long way home after work, pop in a movie, and relax. I steadily worked my way through my Netflix queue. I didn’t feel rushed, had no real obligations outside of work, and set all my own rules. It was glorious.

Soon, however, I began craving social interaction, with some caveats. I did not want to be busy every night of the week; I was enjoying my time to myself way too much. I had no interest in loud bars or clubs, paying for uninteresting movies because I was invited, or staying out until all hours of the night. Whenever I’d ask someone what was going on, it usually tended to fall into one of these categories.

Around this time, I began using my free time to try out different organizational systems. I’d read Life Pro Tips, Life Hacks, and blasted through Getting Things Done. I started using a calendar, something I had never done before. I started small, but eventually found a way to use this calendar to become more social and more reliable. It completely changed my life. It can change yours, too.

This is a guide to setting up and using an online calendar based upon my own experiences. If you don’t use a calendar at all, you may benefit from the entire system. Otherwise, maybe there will be a few tips or pointer to help out your current system. This post is for people who may not be content with their current level of activity. Those who want to start going out, being more social, exploring their city, and setting and keeping more obligations. Ready?

Getting Started

If you’re new to keeping a calendar, the best place to start is with paychecks (yay!) and bills (boo!). Make a recurring event for your paycheck, whether that’s weekly, biweekly, monthly, or whichever (if you don’t have a regular paycheck, you can skip this step, although it may make the methodologies in this section a bit more difficult). Next, take an inventory of every single recurring bill that you have. For me, this includes: rent, gas, electric, internet, Aereo, Backblaze, Github, 23andme, student loans, credit cards, cell phone, and renter’s insurance. You may have more, you may have less. But make sure you get everything — if you have certain bills that automatically charge to a credit card, you’re welcome to just put the credit card payment on your calendar rather than each smaller bill. Remember, set all of these calendar items as recurring events since they happen every month.

At this point, you’ll already be feeling better. Well, maybe you’ll be panicking (where did all those bills come from?) but subconsciously you’ll be feeling better. Having your entire monetary situation laid out in front of you is liberating. From now on, you’ll never have an “oh shit! I forgot about that bill!” moment.

If your money situation is tight and/or you’re living paycheck to paycheck (who’s got two thumbs and relates? This guy.), here’s a habit that may help you: Every payday, open your calendar and note every single bill that falls between the current date and your next payday. Pay every single one of those bills immediately. Then toss a bit into savings. The rest is yours to live off until your next paycheck! Pretty soon, you’ll have a pretty good feel for your food budget, transportation costs, and other expenses (pet care, gift shopping, the occasional splurge, etc.). If you see that your next paycheck is going to be tight but your current paycheck has a little wiggle room, stash some of that money away to help yourself later.

Keep in mind, falling into this habit may take some time. It may feel harder than your old habits at first. But you’ll be sleeping better knowing that you’re in control of your life. You’ll know exactly who needs to be paid, when, and how much extra money you have. Your weekend out with friends won’t accidentally cut into your rent money (assuming that knowledge of your money situation will help you make better decisions…) and you’ll know how much can be reasonably stashed away for the latest tech gadget.

Start Making Commitments (and Keep Them)

There is one simple-sounding piece of advice that I consider to be the most important thing anyone ever told me: Make commitments and keep them. I was first given this advice as a senior in high school but it took me many years before I truly understood the meaning. There was even more time before I took those words to heart.

Even when I made a conscious decision to be more social, I’d still find myself often sitting at home with nothing to do. I had told myself that I wanted to get out and do more things, but it just didn’t seem to happen.

I realized there were two main reasons for my lack of plans: 1) I wasn’t in the mood/didn’t have the money do to anything my friends were already doing, and 2) I avoided making plans because I never had a good system to find, organize, and track of all these commitments.

I decided to try an experiment. I started planning my life one week in advance. I started with just one night a week in the future. I’d think of a friend I hadn’t seen in a while, ask if they wanted to grab a drink or a cup of coffee — something that was appealing to me. the following week after work. If they agreed, I’d suggest a random day until we settled on a date, picked a bar or coffee shop (if you’re inviting someone to meet up, always make the first suggestion for a place to meet. This gives you control over atmosphere and pricing. More often than not, your friend will agree. People don’t like making decisions; they’d rather be told what to do), and entered that into my calendar. I got in the habit of checking my calendar every morning to see the events planned for that day. If I had plans, I’d email or text my friend to confirm.

Making the transition from event attendee to event planner is quite difficult. If you’re usually the one that accepts plans, rather than the one who makes plans, start small. Think of one friend you haven’t seen in a while, think of an activity you’ve done with that friend in the past, and ask if they want to do it again. Don’t try to organize large parties or even events with groups of friends. Just stick to one person and one schedule to coordinate with, and go from there. The best part about being an event planner is that you get to choose what you want to do. If you feel awkward choosing the restaurant or event, just imagine your reaction if your friend had made a restaurant or event suggestion to you. You’d likely be totally happy with it, and that’s probably how your friend feels as well.

Pretty soon my random evening events turned into weekly meetings. I started going to a local bar every Monday evening with a few friends. I also began going to another friend’s apartment once a week to watch the new episode of Lost (we’d watch old episodes between new seasons). This lead to the realization that there were other friends I hadn’t seen in a while, and so I contacted them and put them in my calendar for the next week.

After a month or two, I had to start scheduling “nights off” into my calendar. Despite being a homebody, this was an empowering shift for me. I was now in complete control of my time. If I felt like staying home and doing nothing, I could make a decision to avoid plans a certain night. Doing nothing was no longer a default option, it was a conscious choice, and my nights “off” were even more enjoyable.

Make Plans for the Future

Now that you have a rhythm and flow to your life and plans, it’s time to start playing around a bit. Open up your calendar in one browser tab and check for upcoming events or activities in next weeks or months in another. As soon as you find something interesting, check your calendar and if that date is clear, write it in. You can worry about finding people to accompany you later (most of your friend’s plans will probably still be a bit fuzzy far into the future anyway). Just start adding fun things you want to do to your calendar.

At first it may be hard to find things to do. Before using a calendar, I had never really planned anything in advance so I had no idea what sort of things were going on in my area. Here are a few ideas to start your search:

  • concerts
  • museum exhibitions
  • movie premiers
  • readings
  • art gallery openings
  • classes (if you’re in New York, check out CourseHorse!)
  • workshops
  • massages/spa appointments (if you’re in NY, LA, SF, or CHI, check out Lifebooker!)
  • daily deals (everyone should check out Yipit)
  • Meetup
  • Skillshare
  • day trips

Add anything and everything of interest to your calendar. Remember, you’re not committing to these events, you’re reminding yourself of interesting things to do.

After everything is added to your calendar, keep the same weekly routine and plan your life one week in advance. Check your calendar, see what’s coming up the following week, and make a decision about each night. Maybe a friend or two might be interested in checking out a certain art gallery opening you saved. Perhaps you got a daily deal to an Italian restaurant and your friend loves Italian food. Or, even though there’s a ton of events going on that week, maybe you’re in the mood to just stay home and play video games. You’ll now be able to make an informed decision and feel confident that you explored all your options. You’ll have more fun no matter what you decide to do.

If you decide to stay at home but find that you wish you had gone out instead (or vice versa), all you have to do is plan the upcoming week accordingly.

Keep It Going

As with any organizational system, power comes from consistent use. It’s about learning new habits by force in the beginning. This system gets easier over time as you’ll come to rely on your calendar more and more. Happy planning!

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