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An Extrovert's Guide to Living Alone

Yvonne Boulay
A three image collage of an empty apartment, a girl taking a photo of her shadow on the ground, and four friends hanging out

There I was – sitting on my bed staring at my phone for an embarrassingly long amount of time – and it suddenly dawned on me: I’m about to live alone.

While I may not be an expert on the subject, I can assure you that I got hit with the cold, hard reality of living alone as an extrovert. 

I went from having three roommates, to one, to none within a 6 month time frame. To give some context of my situation, I finished college living in an apartment with 3 of my best friends. One of those friends was also about to attend the same university for graduate school that I was, so it was an easy decision to live together again. Little did we know that she would be spending half of our lease in a different state due to an amazing internship opportunity. 

In my situation, I was unprepared to live all by myself – but you don’t have to be.

Because I’m still relatively new to the solo-living world, I’ve teamed up with Jillian Richardson, coach and author of Un-Lonely Planet, to share some of her expert tips on how to foster deep connection. That way, our combined personal experience from both the beginning of this daunting journey, as well as the hindsight from someone that’s been through it, can help you navigate this uncharted territory.

Meaningful Social Interaction

While you may be craving friendship in your new living situation, you may have to accept that it’s best to start small. Meaningful social interaction can take many different forms. I noticed a huge difference in my mood and disposition when I had even the smallest exchange with a stranger. Compliment the barista at your local coffee shop, ask the waitress for nightlife recommendations, and share a quip about the weather with the cashier at the grocery store. A smile can go a long way if you’re not used to being alone.

Not knowing anyone in the city you’re moving to is also a huge lifestyle shift. Even in my case for graduate school, it can sometimes be hard establishing friendships with someone to only see during an hour of class time. Not only was I thrust into adulthood, but I was doing it (mostly) alone. I had to get creative with ways to spend my time.

Jillian recommends making meaning friendships through community meet-up groups:

“My biggest tip: think about the type of person you want to become. Where would they hang out? Do you want to meditate more? Check out a local zen center. Do you wish you were a morning exercise person? Check out Daybreaker! This tactic is a great way to narrow the playing field, and make the idea of meeting new people a little less overwhelming. I learned so much about myself this way, and having a consistent meeting point every month helped to deepen connections."

Planning Takes Effort

If you’re like me and always seem to be going on little adventures at the drop of a hat, you’ll begin to realize that you’ll have to be much more proactive when it comes to making plans when you live by yourself. You’re even more like me if you find it difficult to reach out in fear that it’s been too long or you may be bothering someone. 

Now is also the perfect time to reach out to that one mutual friend you noticed is also in your city. A low stakes outing like lunch or a walk in the park will be the best way if you want to create a new, old connection. Seeing other people takes more effort than before, but you will never regret it afterwards. 

Virtual Plans Count Too

Whenever I desperately needed some social interaction, I would use it as a reason to reach out to people I haven’t spoken to in awhile. A couple of hour-long Facetime sessions with old teammates, sorority sisters, childhood friends, and traveling buddies was the best medicine. It’ll make their day, even if it’s just swiping up on an Instagram story just to tell them they look great. Plus, call home every once in a while. I’m sure mom or dad would love to hear how you’re doing. 

A Creature of Habit

I found myself happiest living alone when I had a schedule to stick to. Not just with classes or work, but when I scheduled time to be by myself around others. Every Saturday I would go to the local farmer’s market and pop into every stall the vendors had. I also utilized common spaces in my apartment complex. This may be tougher if you live in an old walk-up apartment, but amenities mean more chances to socialize. I went to the pool at the end of most of my spring and summer days, either to tan or to read a good book (and might I recommend Un-Lonely Planet by Jillian Richardson). Any social interaction I had boosted my mood, no matter how short. 

Journaling became a healthy habit for Jillian, and she could not recommend it enough.

“Oh, journaling is my JAM. If you want a fun way to get started, and you’ve got some extra time, I highly recommend The Artist's Way by Julia Cameron. It not only gets you going with a morning journaling practice, but it also gives you a lot of ways to reflect on where your creativity might be stuck. When I did The Artist’s Way, I ended up moving. I know other people have ended relationships, shifted careers, and totally changed their lives. So if you do that book, be prepared for some shifts!”

While living alone, I joined a soccer league, went to sporting events with new like-minded friends, and revived my love of painting.

Make Your Home Somewhere You Want To Be

I used my spare time to carefully curate my living space and decorate the way that I wanted. I always felt that I had to be running out the door to be happy, but I realize in hindsight that having a cozy space that to come home to made living alone even better. In my case, I marched myself to CVS, bought a couple magazines, and spent a night with a glass of wine making a collage for my wall. You don’t need to be an artist to decorate, but dedicating personal time to make your apartment home will always be worth it. 

Take Yourself On Dates

You may have heard advice, “Just got out to a restaurant by yourself! It’s liberating!” In my humble opinion, being waited on when it’s just you is a little too awkward for most. My solution was a much easier adjustment: taking myself on walks. I would put my headphones in, make a pit stop to a local coffee shop, and walk through the local park. As I got more comfortable on my solo adventures, I began stopping in local thrift stores, buying some plants, and treating myself to some take out to eat when I got home. Not only will you be able to explore more of your city, you’ll also get the benefit of getting your steps in.

Jillian surprised herself by spending more time on her own. She actually discovered she was an introvert!

“I think the pandemic, as well as growing older, has taught me that I gain the most energy from one-on-one or small group interactions.Crowded and/or loud environments, especially ones where people are drinking, are pretty intolerable to me now. And despite what people might think, that still leaves a lot of fun ways that I can socialize!”

A cute farmers market date with yourself is a great way to explore your new city.
I look forward to my 'date days' every week because they make running errands fun!

Talk It Out

One of the things I missed most about no longer having a roommate was having someone to rant about my day with when I came home. My thoughts are always swirling around in my head, and sometimes you just need to tell someone something small like about the guy that cut you off in traffic or the new construction you noticed down the street. Having a sounding board as an extrovert is extremely important. If you’re feeling lonely, have a conversation with a family member or friend and try to work out solutions. Ironically, venting to someone else may help you find joy in being alone.

Check In With Yourself

Living on your own will also mean living in your own head for longer periods of time. You can only be distracted by your phone or a TV binge for so long. A positive internal pep talk is crucial to processing big emotions without a trusted friend in the room nextdoor that you can lean on. Post-pandemic, I think we are all now hyper aware of how mindful we need to be if we spend so much time away from others. It’s okay to feel lonely! Checking in with yourself, journaling, and other healthy habits should become a top priority.

Jillian admits that sometimes, it’s best to take a break. 

“And that’s okay! As long as you have some form of social connection, I think it’s okay to go for a few weeks without “putting yourself out there.” Doing so can be really draining, especially if it isn’t going as planned. And, chances are, if you give yourself permission to take a break, it might end up being shorter than you actually think you need.”

Living alone takes practice. It’s easy to get discouraged – I struggled with the adjustment longer than I’d like to admit. However, I actually surprised myself with how much I loved my time living alone. 

If you want to learn more about Jillian Richardson and her strides to foster community in an era of disconnection, I highly recommend you check out her website here. If you live in New York City, sign-up for The Joy List: Jillian’s weekly newsletter of community-centered events in NYC!

We wish you luck on your solo adventure. Now it’s time to get out there and enjoy it. 

Jillian has been featured as a source for The Wall Street Journal, The Guardian, and NBC, among many other outlets. Jillian helps people learn the skills to connect more deeply to themselves and others, and has inspired thousands through her workshops, interviews, and public speaking engagements. Jillian loves everything under the umbrella of connection, and dives into topics from friendship to dating and spirituality.