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Solo-preneur & Company

Loneliness is real, especially if you work freelance. Over the years I've come to recognize that one of my triggers for loneliness (apart from genuinely missing friends and family that live far away) is feeling overwhelmed with all of the "life admin" that can stack up. Running hard and fast our goals can sometimes make us lose track of ourselves and our relationships. Solo-preneurs beware: it can look like glamorous freedom from the 9-5 grind, but it can feel like a lonely well if we're not careful.


How to stay ahead of loneliness (or at least manage it when does come up) is all about developing systems and self-awareness. Over the past six years of freelancing, I have created weekly and monthly structures that are flexible, but also hold me accountable to the things I need to do so that when I am around others I can be more present and enjoy them. Even if you're not self-employed, there are likely still some nuggets here for you, especially if you read to the end.


So here are my ten practical tips for when the "lone-lies" hit (from obvious to overlooked):


1. Call a friend or family member. Have you noticed that we tend to talk on the phone less? We text and tag, but it's not true connection. Pick up the phone and call. Better yet, FaceTime. Middle of the workday or people not answering? Schedule a phone date. Or send a text just to let someone know you're thinking about them. You may not get an immediate response, but it can remind you of your connections and it helps nourish the relationship for when you do see them. I try to send five to ten "touches" per week, sometimes even prefaced with a "no need to respond... just wanted you to know..." More often than not, I hear back and I feel better.


2. Listen to a podcast. I'd heard people mention podcasts for years before I got around to actually listening to them. I wish I'd done it a lot sooner. When you find a podcast you really like, you're not only learning something new, it starts to feel like a friendship with someone you haven't even met. For me, feeling this connection and knowing how similar we all really are (even amidst our valuable differences) starts to shrink that feeling of alone-ness in the world. Seriously, put on a podcast and go for a walk the next time you hit a lonely lull. It almost always shifts my mood. And if you want to know my top five leave a comment below and I'll happily share.


3. Take a class, dust off your hobby, or take yourself out on a date. It may sound cliche, but there's a reason you've likely heard someone suggest "pick a hobby" as a cure for loneliness. When striking out to go do that thing you're really into (or have nervously considered), it puts you around new people who share common interests. There's a strong possibility that you will meet some new people and maybe even make a new friend. Even if you don't, it will build your confidence support the process of learning to enjoy your own company which, my friends, is an important lifelong skill that we will return to.


4. Talk to strangers. Stranger danger may have been over emphasized when we were kids. Proceed with caution, yes, but trust your gut. Numerous studies have shown that even small talk with a random stranger can improve our mood and make us feel more connected. Have you ever felt lonesome and decided to be productive to take your mind off of it? Maybe you head for a work out or go run errands, but we often make a mistake here: being glued to our phones and plugging our ears with headphones. I've been just as guilty as most. But hello! You just passed like 30 people. People are everywhere and guess what? We all crave connection. More often than not, people want to engage with others, they're just scared to. So the next time you're grocery shopping or on public transit-- any of the dozens of times throughout the week you may actually be around other humans-- look up. Be bold. Say hi. Pay them a compliment or ask them a question. Talk about the weather. Just open your mouth. Yes, it might feel awkward. No, they likely won't become your new best friend or may not even be interested in talking to you, but chances are: you could make their day and yours.


5. Stop using social media as a platform for comparison. You guys, this is real. Social media can be a great tool, but its designed in a way that can confirm your natural bias against your own cool factor, especially when you're in a vulnerable spell of loneliness. Social comparison can undermine our feelings of connectedness and self-agency. Mindlessly scrolling with subconscious subtitles like "I wish I was that successful/cool/carefree" or any other thought toxins that make you feel less than your amazing self are only fueling your loneliness. Thinking about how few likes and followers you have compared to that chick who always looks great, has clever captions and seems permanently on a glamorous vacation is a lonely freelancer's deathtrap. Trust me, I've been there. So, watch your self-talk and make sure you have some clear, healthy boundaries in place on why and how you are using the gram.


6. Start a meet-up (or join someone else's). This may seem like a cheesy one and it does take some effort/planning, but it dramatically increases your odds of feeling more connected. Freelance life can be freeing, but oh so isolating. I'm apart of this online community called GirlBoss and I get emails with updates on announcements about all sorts of interesting things. Recently, this cool, brave gal posted that she was looking to start a meetup in SF that was part work accountability, part idea tank, part social hour. (LOVE IT!) I responded along with about 15 other ladies around the Bay Area and now we have this email thread going with plans to meet up. We haven't even met IRL and already I feel more connected in my community. So, start a book club, a brunch club, a hiking group, a bar hopper's guild (careful with this one), a game night or even a monthly outdoor picnic party! (Seriously, anyone down for a picnic party? Cuz Spring is just around the corner, warm weather lovers.)


7 Avoid numbing out. I realize this is a loaded one and at the risk of losing some of you, this hits hard on what I meant by self-awareness, so stick with me. Humans are creatures of habit and most of us have efficiencies for shortcutting inevitable uncomfortable feelings... but at what cost? What I've learned is that these "negative" states are often invitations for growth in disguise. I'm guessing you're feeling less than amazing a few times each week, am I right? Dread, fear, confusion, shame, anxiety... or maybe you're not even sure what that gnawing feeling is. Either way, not fun. At their best they are extremely uncomfortable and at their worst these states might send us running for activities that (may give immediate relief, but ultimately) make it worse. You know what I'm talking about: habitual or heavy drinking, smoking, overeating, aggression, excessive sleeping, binge watching Netflix for days on end, or any other activity that serves to hide you from yourself and the feelings of worthlessness you're shoving down with that whole gallon of ice cream. It may seem like I'm being harsh here, but I want to be clear: I'm talking to and about myself. Former stoner, alcoholic, pill popper (please God, don't let my dad read this), reformed codependent, healing overeater, and still clearly in the throes of battling workaholism. It's not that any of the things in these equations are bad, it's the underlying thoughts and motivations that can be problematic. While my intention is not to make you feel badly about yourself (numbing is very normalized in our society, so please be compassionate with yourself), I do hope to make you stop and think. Are your daily habits serving you or blocking you from becoming who you want to be?


Making change can be tough work, but so worth the effort. Initiating changes in these domains started a chain reaction of shifts for me that has dramatically changed my life. If you thought that was heavy, hang on: I got one more doozy for ya...


8. Seek Therapy. I know, I just went there. Honestly, I almost left this one out, but it's important. Sometimes we are lonely, but sometimes we feel this because we are going through something really hard and we don't want to burden others with it. When I was in my early twenties, I was raped and even though I'd opened up to a couple of friends about it, they couldn't give me the support I truly needed to begin healing. After deeply struggling for over a year, it was clear that this was something I needed to do. So began five years of weekly therapy with a woman that truly changed my life by helping me rebuild my relationship with myself and reframe what had happened. If you're dealing with a trauma, loss, or even just deep confusion, you are bound to feel alone-- amongst many other things-- and you owe it to yourself to talk to someone. Friends and family can be a great support (if you're lucky), but sometimes we need an objective, trained perspective. I did. Maybe it's worth asking yourself if that feels true for you. No stigmas here. Mental and emotional health are the foundation of a fulfilling life.


9. Invest in yourself. Do things that matter to you and learn to enjoy your own company. As humans we need others to thrive and it's true that too much alone time can be detrimental, but learning to enjoy your time alone is also a necessary part of holistic health. Are you always running from deadline to side project to client meeting and wondering why your brief moments alone feel sharply lousy? Hopefully not, but if so it's time to check in. Maybe it's time to reprioritize your self-care regimen or even reorganize your definition of "selfishness." Are you avoiding spending time alone? The truth is loneliness is just a feeling and while it can be very uncomfortable, I promise you it is more uncomfortable to spend all of your energy trying to outrun it rather than simply letting yourself relax into it.


The next time you feel lonely try just hanging out in it. Start or finish that book you've had on your nightstand. Research that idea that's been in the back of your head. Start your blog or podcast or book. Work on that painting. Put on some music, light a candle and dance (or cry) or both. I'm serious, sis...(or bro. Do I have any male readers? Other than you, Ray). There's a lot of power in letting yourself feel your emotions. If you do, you might find that just like clouds on a rainy day, eventually they will pass and the sunshine will emerge right around the time you were finding the courage to dance willingly in the rain.


10. Plan an exciting trip with someone you love. It doesn't even have to be a big trip. It could be a stay-cation. Having something to look forward to is often a light at the end of a lonely tunnel. My mom calls our visits "money in the bank" and it truly feels that way. When I first moved to the Bay Area ten years ago, I was fresh out of college and ready to start my dream life. I moved here with no friends or job prospects, but a whole bunch of optimism and a strong will to make some major changes in my life. I knew it would be hard starting over with friends, but I didn't know how hard. Two years in and while I'd made a couple of friends, I was unprepared for the level of loneliness I felt. I may or may not have spent my twenty fifth birthday working, going to yoga and then crying over a cupcake and a bottle of wine in my home office. What helped in that moment, and each day that I really struggled in those early years was telling myself that I just had to make it through to my visits home. Knowing that I was going to see my friends and family, even six months down the road, motivated me to find creative ways to occupy my time.


11. I know I said ten tips, but this one's a bonus because I love angel numbers, writing, and you: Remember that you're never truly alone. Even if it feels that way. It's a poignant truth that no matter how blessed and surrounded by love we are, we all feel alone. Welcome to the human condition. In part, the struggle has instilled in me the responsibility to manage my inner terrain in ways that allow me to show up more fully out in the world. It reminds me that beneath my physical, emotional and mental health there is a spiritual core that grows or shrinks in correlation with my attention.


In the hustle of goal crushing and project-juggling it's so easy to let our holistic health slide to the back burner. Our work as entrepreneurs, as humans, becomes tending to our spiritual needs. You cannot deliver results to others if you're not able or willing to deliver love to yourself. Unconditional love comes from a connection to a higher power.


 This is certainly not where I try to push any beliefs on you (truth be told I'm still finding what mine are). I don't care if you go to church or pray to Allah or practice zen meditation, but I do care about you. I hope that at your core, you have some kind of guiding beliefs that ease your inevitable questions and pains and help you make sense of our aching world. No matter what your spiritual beliefs are, you must have some kind of north star; some guiding force that can cut through any awful situation and renew your belief that it all matters, even if you're not sure how yet.


If you've been feeling lonely, consider it an invitation to investigate what brings meaning to your life. In large part it's our relationships, but these can only be as strong as our willingness to show up for ourselves. So, here we are full circle at the importance of growing self-awareness and systems in our lives. With practice these help us connect to our passion and purpose. Relationships ebb and flow and while they do, my freelance friends, look at loneliness as an opportunity to build a stronger relationship with yourself. Be your own friend and be a damn good one! Trust that the next time you fall flat on your ass in a puddle of loneliness, you have the tools to move through it. It's not about having the answers, it's about having the courage to live the questions that invariably unfold on your journey. Trust this and it will no doubt open you to exciting new horizons of yourself... with loneliness eventually missing you.


Wishing you peace, dear ones.




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