Making time for friends and finding a support system is key. Above: Couple of hombres grabbing KBBQ in LA.

This post is a build-up of thoughts over the past few months, many of which are embodied in past posts. See ‘Living or Visiting’, ‘Being Over-Productive’, and ‘2019 — Checking In’ if you haven’t already.

My generation is known for consumerism, being glued to technology, and being transient. The first two are a given; we love to shop, have more credit card debt and spend the most time online compared to other generations. The third is not as clear; what does ‘transient’ mean?

I’m referring to our tendency to switch jobs and move cities more than anyone else. In this post, I want to deconstruct some of the stereotypes about Millennials, why they make it challenging to build community, and how I think things could change.

“Your 20s are for exploring”

I’ve moved a lot in the past few years, spending a considerable amount of time in San Francisco and Los Angeles, with stints in New York City. For my peers, travel is embedded in the culture; it started with the 2-6 month graduation trip, and is supplemented with frequent vacations while working until another prolonged trip after the inevitable quarter-life crisis.

I used to idolize the ‘digital nomad’ lifestyle, where you can work while travelling the globe, meet new people everyday, and be unrestricted by monotonous routines. Now, I want a ‘home base’ more than ever. I hate the popular phrase “Your 20s are for exploring”; what does ‘exploring’ really mean? Is it travelling the world to expose yourself to new cultures, people, and experiences? Or is it the desire to reject a regular job/lifestyle, prove yourself different from the status quo, and avoid falling into the same tendencies (steady job, family, routine) that our parents did?

I spoke with a friend recently who was amazed by someone who rotated between NYC, SF, LA, and Austin over a 3-4 year period. It’s not the moving that I’m surprised by: I left San Francisco because I hated the city, and left LA because while I enjoyed being there, I didn’t fall in love with the city / want to call it home. My biggest question to these people is: Did none of those cities fit your criteria for a good place to live? In other words, are you even looking for a ‘home base’?

Maybe I’m guilty of putting too much emphasis on the idea of a ‘home base’, but allow me to explain. I think the reason I search for a home base is the following:

A consistent circle of friends with whom I have physical interactions with
A routine that involves fitness, hobbies, and some cultural elements native to the city
A place that I can furnish, alter to my liking, and call ‘home’

The first point stems from my personal experience: over the past few years, I haven’t ‘lived’ in one place for very long. This means that some of my closest friends are dispersed: SF, NYC, LA, and beyond. I don’t mind this, as occasional trips, video calls, and other forms of technology make me feel quite connected. However, it doesn’t replace in-person interaction. I’m not ‘plugged in’ to the Toronto community, partially because I haven’t made the effort but also because I don’t know if I’ll be here in 4-6 months. I think a home base would solve this problem.

I’ve heard the second point echoed by friends who also travel frequently, namely consultants or people in international roles. Fitness is a result of having access to a gym, which you don’t have when you’re constantly travelling. This changes when you stay in a city for longer than 2-3 weeks, but makes it challenging to build a routine involving sports leagues, companions to work out with, etc. I find hobbies to be quite similar; I like stand-up comedy and art, but exploring the city in search of those things without a strong friend group can be challenging.

The third point is the best embodiment of the nomadic / transient lifestyle. If I’m staying in a city for less than 6 months (which is often the case), why would I buy furniture, decorations, and other houseware? There’s no chance I’m packing posters and other items in a suitcase, given how cumbersome it is to travel in the first place. Since working, I don’t think I’ve ever called one place ‘home’ and made any effort to transform it into that.

Maybe some of these observations are more a fault of my own than a consequence of culture. I can make an effort to meet people and get ‘plugged in’ to my city. But why invest in something that you know probably won’t last? It’s not hard to make friends in a new place, but what about good friends? Ones that you actively want to hang out with, who reach out to you when they want to do things, and who you can invest in (with regards to vulnerability / thoughts) and they reciprocate?

More than anything, I believe this is a consequence of being busy / not having enough time. Which brings me to the second phase I hate…

“Your 20s are for grinding”

I hear this phrase time and time again, coupled with “I hate my job, but has to be done” and “I can chill when I’m older”. I think it’s ironic that the same people who love to travel and thrive on new experiences shackle themselves to jobs that do the exact opposite. I’ll put this differently, focusing on my own experience: I don’t want to ‘grind’ until I’m 30. I don’t want to work insane hours creating value for someone where I don’t benefit. I don’t want to reject desires for stability, time with family, and time for relaxation / mental recovery in the name of ‘the grind’.

Why does any of this matter? I think it directly relates to building community and the transient nature of millennials. I think about 30% of my life, and the value I associate with it, is tied to my career. The remainder involves family, relationships, and physical / mental health. To give a practical example, and this should be visualized as a pie chart for time/attention VS a hierarchy of value, see below:

30% work
30% relationship
20% family
20% personal health

How I approach my day-to-day should reflect this, but I don’t think that’s the case. First, my current schedule and level of prioritization is skewed too far towards career. Second, I don’t think the majority of my friends accept the 30% breakdown, and might believe it’s closer to 60% or even 75%.

Now let’s move from attention breakdown to my actual schedule. Assuming I wake up at 8am everyday and sleep at 12am, that gives me 16 hours each weekday. On weekends, I usually wake up around 11am and sleep around 2am. That gives me 15 hours on weekends. Overall: 110 hours a week.

Currently, my 110-hour week looks like this:

Work: 60 hours per week (usually 9-6, with time in evenings + weekends)
School: 15 hours per week
Family: 3 hours per week (I’m rarely home)
Relationship: 15 hours per week
Personal Health: 17 hours per week (TV, working out, eating, etc.)

What should this actually look like?

Work: 50 hours per week (keeping 9-5, plus some email / urgent items)
Family: 7 hours per week (being physically there, or engaging with them more)
Relationship: 18 hours per week
Social Life: 10 hours per week (intentional time with friends, getting ‘out of the house’, etc.)
Personal Health: 25 hours per week (same as before but add in reading, exploring city/hobbies)

Key differences between the two: spending 15 hours less on work, significantly more time on family, and re-allocating time from school (which I’ve revisited + will be done in the New Year) towards social life, my relationship, and personal health.

If you’re like me, then you also have a realistic time breakdown VS an ideal that you want to accomplish. The question I grapple with is: how should I alter my lifestyle to achieve this balance, and invest more heavily in building community and caring about personal/mental health? As with most of my posts, here comes the ‘action’ step.

Step 1 — Operationalize Work + Set Boundaries

I’m sure some of my friends reading this will laugh at the 60-hour work week. Jobs that really ‘grind’ you should lead to 90-hour or 100-hour weeks. So I’ll give some colour to this: running my own business means that I don’t have an office, regular work hours, or a boss that has expectations of me. There are tons of pros here, namely that I avoid the ‘face time’ issue and spend 90% of my work day actually working VS sitting in meetings, waiting on other people, or doing unnecessary tasks that are delegated to me. There are also lots of cons: if I drop the ball on a client and they churn, I lose 20% of my monthly salary. I need to define what ‘good work’ is: how much I should be working and what quality of work I need to deliver.

I think there are learnings here that can be applied to everyone. For starters, operationalizing work is a concept that I obsess over being in the services business, but can benefit people in full-time work as well. How do I handle email? What is my expected response time? How well do I communicate the work I’m doing? Do I have tools for prioritization and staying on top of things?

The short answer is yes, I’ve figured out parts of this. I use Asana to manage my agency work, set deadlines, and know what I need to accomplish. I use Superhuman for email; despite all the hate it gets, I find it easy to manage my inbox and avoid falling behind.

There are tons of areas where this can improve, so I’ll think aloud here:

Automation — I’m a HUGE advocate of Zapier, but I don’t use it as much as I should. What parts of my work take up ‘mental space’ that can be automated here? Is it reporting for clients? Maybe it’s payroll at the end of the month?
Prioritization — What are clients expecting from me + how do I become proactive about this? Instead of ‘firing from the hip’, maybe I should be blocking off parts of my week to plan ahead, do a post-mortem on campaigns + evaluate client relationships.
Outsourcing — MAJOR issue right now; what am I executing on that I don’t need to be? How do I hire freelancers effectively, try them out, and either pursue if it works out or end the relationship? We’ve used UpWork and personal networks for this, but I think there’s a lot more to be done.

The second area is setting boundaries. Even when I was working full-time for a company, how I carried myself and operated was largely defined by me. If my boss sent me an email that was non-urgent, how long did I take to respond? Do I respond on weekends? Do I even work on weekends? I have a friend in VC who used to work insane hours and now holds himself to a 9-5. He said he’s 10x more effective, because he respects the boundaries he sets for himself. His colleagues / boss know this too — no point sending an email on the weekend if he won’t read it until Monday.

Step 2 — Invest in people

Currently, I don’t put an adequate amount of thought / effort into social interaction. I don’t have a tightly knit friend group in Toronto, and that’s largely my fault. When life is non-stop, it’s hard to be intentional about keeping up with friends (both in your city and abroad) and meeting up with people. As I’ve mentioned in past posts, I have gone as far as trying to spreadsheet this to ensure I’m not falling behind. It works if I keep up with it, which I don’t. How does anyone do this effectively?

An older friend gave me this advice (paraphrased), which I’d like to implement a lot more than I do:

In your life, you have many 5-7 friends who you are very tight with. You interact with them on a daily basis, share your life, and support them where you can. On top of this, there’s another 20 friends who are in your circle. You enjoy hanging out with them, see them when you can, but it’s likely a weekly or bi-weekly thing. Then, there’s another 50 friends in the ‘extended’ network. You see them / interact with them every few months, but it’s usually a catch-up and not anything deep.

I currently do a horrible job of this. I’m good at crafting the ‘20 friends’ group but have trouble investing in them to have a strong support system of 5-7 friends. I know social engineering is frowned upon, but I’m genuinely interested in how I could improve this. I think the solution is to really double-down on the people I love hanging out with, who (in Marie Kondo fashion) ‘bring me joy’. This starts with messaging those people more frequently than I currently do, but it also extends to the depth of the relationship. Am I asking questions that are surface-level? “How’s X person, how’s your job going”? Or do I dig deeper into “What’s bumming you out this week? Any personal goals you’re trying to hit in the next month”?

I have some quirky ideas on how I can set this up, re: calendar reminders and other nudges (which I already do, to some extent). Regardless of how this plays out, I think the other thing to keep in mind is that these efforts will not always be reciprocated. More wise advice from another older friend:

You’ll meet people who you really vibe with, and you want to be good friends with. ‘Damn, that person is cool and I want to be best friends with them’. So you’ll message them frequently, ask to meet up, see how they’re doing, etc. Sometimes, certain people won’t reciprocate. They’re too busy, or they already have that 5-7 person group. No worries — just move on to other people who will reciprocate, and leave that door open.

That’s a hard pill to swallow, but I want to internalize it. I have message histories where I ask someone every week how things are going, and usually get a ‘sorry for the late reply, let’s catch up soon’. I do the EXACT same thing with other people, and I feel terrible about it. For the former, maybe I should accept it’s not the right timing (for now) and move on. For the latter, maybe those people should do the same for me.

Step 3 — Self care and saying NO

Another thing I hate about the millennial generation: we all love talking about the importance of mental health, self care, etc., but I feel like that’s rarely put into practice. How many times (and I’m guilty of this too) have you messaged someone “how are things going” and the response is almost always “good”. This is probably a consequence of the 5-7 friends VS 20 friends VS 50 friends buckets, but I think there needs to be a shift here. Why am I not more honest about when I’m feeling terrible and what I’m struggling with?

Making time for yourself is important. It’s even more important to know that you never have to justify it. I ran into this issue this past Friday: I had a rough week, was feeling pretty stressed, and (as an extrovert) my default reaction was to message people and try to hit the town. What ended up happening? I took a night off, stayed in + watched Netflix and got a solid night of sleep.

This was a great decision, and in the future should be coupled with reading, working out, and even cooking for myself. I don’t owe it to anyone to be ‘always on’, or to rationalize why I’m doing absolutely nothing on a Friday night. Making time to recharge, reflect on my week, and get my mind in order is key for self care.

Saying ‘No’ is a big part of this. I’m guilty of this on both ends: when someone reaches out asking for a call or to meet up, my default response is ‘of course!’. Likewise, I’ll spark conversation with someone (usually on their birthday) and feel obligated to pitch a meet-up or call. I almost want to get ‘say no’ taped to my laptop — most of the time these catch-ups or calls are unnecessary, as harsh as that sounds, and can be done over Messenger / asynchronously. One of the reasons I loved LA is that it was so easy to say ‘No’, since everyone was at least a 30-45 min Uber ride away! I want to reclaim my time / schedule, and I think it starts with intentionally making time for self care and saying ‘no’.

Conclusion

This was a super long post, so I applaud you if you made it this far. Like many of my posts, this is purely an exercise of self-reflection. I don’t mean to call anyone out or say that ‘my generation’ or certain viewpoints are ‘wrong’. The main point is that I find that millennials (myself included) are too obsessed with work and new experiences that we forget the value of community and healthy lifestyles. I’m also quite disappointed in the amount I’ve invested in my friends and intentioniilty here, and want to improve.

If you disagree with my thought process / approach, please message me (Facebook, Twitter, etc.) or shoot an email to trevor.sookraj@gmail.com, I’d love your thoughts! Thanks for reading :)

P.S: I also want to apologize for my writing hiatus; it’s been more than 3 months since my last post. These past few months of juggling my marketing agency and keeping up with friends/relationship/personal health have been incredibly challenging. I’ve never felt this drained or unhappy. Thanks to friends and family that have supported me throughout this — you know who you are :)