Move to a city on your own. Cut the financial support chords of family. Start your own business. Whenever you decide to take on life on your own terms, freedom follows.
Starting a business or starting to freelance (alongside the 57 million Americans doing so today) is terrifying, exhilarating, stressful, and liberating. You’re taking total control of your finances, and losing the structure that comes from a 9-to-5. It’s scary, but have you thought of shaking off the normalcy of a 9-to-5 like Joe Holder, trainer to the one and only Naomi Campbell? What about following your anthropological passions like street style photographer Chris Fenimore or antiquities maestro Michael Diaz-Griffith? Or, setting up something you can pass along and like a product or namesake company à la Patrick Kelly, Josh Shaub, and James Vela?
Now is a time that allows some of us the luxury to reflect and start fresh. Pursue your art! Benny Or, Bronze Avery, and Brandon M. Garr all have, and they’re not looking back anytime soon. While there is no guide to freelancing perfectly, no linear path to running a successful business, and no right or wrong way to be the best you, these creatives share how they’ve managed to work for themselves and stay sane while doing so. Read on, and learn how to do both without letting anything fall to the wayside.
Why did you decide to start working for yourself?
Joe Holder: In college I struggled with the normalcy of every day “9-to-5” life, but I also wasn’t cocky enough to accept that I wouldn’t have to do that for a bit. However, it has always been my goal to earn a living in a non-standard way.
Benny Or: I started blogging 4 years ago as a way to keep myself inspired. I never thought it could become a source of income until much later on. When the account started gaining traction, that was when I realized that I had the ability to inspire more than just myself.
Chris Fenimore: I was let go at a previous job and while I was applying to new gigs, I continued freelancing as a photographer to pay my rent in the interim. I figured this would allow me the time and flexibility to find the perfect job for myself. I couldn't find the right gig, but I found I was really enjoying myself taking photos. It didn't feel like work, but I had already provided myself a decent foundation to continue freelancing. This whole thing just sort of snowballed into a year and a half of success; when I say success, I mean the ability to pay my rent and enjoy a nice meal every now and again.
James Vela: It seemed to have been all about timing when I decided to launch Vela NYC in 2018. I had dreamt about having my own business. I started collecting little by little while working at several publications and freelancing with stylists. It led to me wanting to invest my time and effort into something that was truly my own.
Michael Diaz-Griffith: My parents were self-employed when I was growing up, and I always admired their scrappiness and drive, so in a way, I think I've always viewed work through the lens of entrepreneurship. The decision kind of made itself for me––the conditions were just right.
Josh Shaub: I got to a point where I felt I had nowhere to go in my career that I actually wanted to go. I loved the place I worked and the people, but from where I was it seemed like the logical career plan would be to move into executive leadership, and that's not for me.
How did you decide what you wanted to do?
JH: I decided what I wanted to do by finding out what I was good at, which would allow more time to pursue my passions down the road. I’m a believer of doing what you’re good at, things that keep you interested. If you can turn your passion into a job, that’s fine, but I don’t think that’s the path for everyone.
JV: I’ve been passionate about antique jewelry for years and was inspired to finally be able to obtain pieces similar to those I had read about in books. The entrepreneurial spirit in NYC is contagious, I wouldn’t trade it for anything.
MDG: When it came to deciding what I wanted to do as a consultant, I combined strengths I was known for with strengths I was not known for! Both packaged in a forward-looking, hopefully innovative way.
How do you handle the stressors of running your own business?
JH: You need a team. Even if it’s just freelancers or friends and family, get a team. You can’t do it by yourself.
BO: Before the pandemic, I would spend most of my free time covering
CF: I am pretty susceptible to anxiety, so I try to focus on one thing at a time, which is about as clichéd as it comes, but it works. I try to lose myself in my gigs and enjoy them for what they are. I don't pressure myself too much, but I definitely have high expectations going into each shoot.
MDG: If I can schedule flex time between noon and 2:00, or between 4:00 and an event at 6:30, I find I'm able to keep my balance no matter what comes my way. That "extra" may be given over to email or preparing a proposal, but it might also give me a little window to see a museum exhibition that's about to close or walk back from lunch instead of taking the subway. Those pockets in the middle of the day allow
Bronze Avery: To be honest, it's really tough at times and during the pandemic it was even tougher. I'm fortunate enough where I have a lot of experience working from home and that many clients are putting all of their needs into design as they can't create other types of visual content. I think the biggest stressor comes from the fear of saying "no", even when you're too busy. Almost as if you say no, you'll never be asked again. I just have to remind myself that's not true and busyness comes and goes in seasons.
JS: I get up every morning at 7:00 am, and 7:00 am - 8:00 am is totally me time to decompress and do whatever I want. That one hour gives me what I need to get through the day, even if it's just drinking coffee on my balcony looking at the ocean. I wish I could say that I meditated or something, but I have tried it and it just isn't for me.
How has that changed through the pandemic?
JH: The pandemic has allowed me to delegate responsibilities and move slower. I’m not happy to be cooped up inside but I believe this moment in time has forced us all to recalibrate a bit.
BO: I’m enjoying the time at home and focusing more on my own sources of inspiration and allowing that to guide my messaging.
Brandon M. Garr: The pandemic has made me focus more on what I need to do in order to get everything in order.
CF: I saved a lot of money through February and the beginning of March just in case. Part of freelancing successfully is knowing how to budget and knowing how to manage your expectations.
MDG: As with everything else right now, I think we just have to do our best while being gentle with ourselves. Those pockets of flex time I mentioned are collapsing right now with so many conference calls and Zoom meetings on the calendar. My daytime hours are running together more than I'd like, but I get up every now and then to make a pot of tea, which gives me a moment to refocus––and, critically, stretch!
How do you slow down, and how does that help you do your job well?
JH: That grind mentality is overrated. You work harder and smarter by taking breaks! slow down by shutting my phone off, taking breaks, and scheduling in idle time. No one can do their job all the time and expect to be good at it.
BO: Great consistent content is the hallmark of a successful blog and it’s easy to feel like you need to constantly be producing more. Slowing down for me means posting less and in doing so, it forces me to be more critical about what it is that I am pushing out.
CF: I try to count my blessings, and play music that I love, or watch a movie. I talk to close friends about anything other than my situation, or I reach out to friends/contemporaries who have dealt with similar issues and seek their expertise. I don't have a fear of asking questions, and this, coupled with my (intense) need to complete projects earlier then or by a due date, make for a pretty good system of resourcefulness and efficiency.
photo by by Isabella Behravan
Pat Kelly: Schedule everything. Meetings, social calls. This probably works for me as an essential tactic because of my Virgo and Generator tendencies, but it’s a proven way to minimize distraction and improve focus. At the same time, don’t overcommit. If you need to schedule breaks and downtime, do so. There’s no shame in scheduling a two hour evening movie block on your calendar.
BMG: I try to keep a work/life balance. I try and sleep well, I stay away from drugs and alcohol completely, work out and eat well. I try not to think of slowing down or speeding up, but pacing myself instead.
JV: During these past few months, getting a breath of fresh air, working out or going on a walk works wonders. It’s important for me to step away from a task when it feels necessary.
JS: I am big into skincare, so I have a rather expansive regimen. I take my time getting ready (significantly longer than most men) and it's not about primping or looking perfect. But I take my time cleansing, then ice roll my face, then apply an array of serums and SPF. I think taking care of yourself and feeling like you look good helps me perform well in my job. How I present myself to the world is important.
Will you reinvent yourself or your brand post-Covid? How?
BO: Absolutely! Unlike many of my peers in the art blogging community who work in various facets of the industry from curation to PR and gallery management, I am first and foremost a creative. I see art through the lens of an artist and quarantine has inspired me to pursue my own practice of art making. I’ve also been critically examining how I want to present myself online. It’s so important to be more human during these times and I’m looking forward to sharing more of me with my viewers.
PK: We already are re-inventing the brand. We leaned, perhaps too hard, on wholesale channels for word of mouth. It’s been a challenge to figure out resource allocation to offer direct customers an entryway to Sigil—a challenge we are rising to.
BMG: I definitely have some plans for post-covid. I think looking more into the digital world in order to plan for future disasters is a must.
JV: Enhancing the website is definitely a must. My online shop is my main source for sales and it’s time to freshen it up with some exciting new content and more antique jewelry.
JS: I am looking even further into new ways of eco sustainability for both work and life. I read somewhere that if you don't leave this experience with either a new skill or new knowledge then, what have you been doing with your time? I would like to come out of this with a new set of both.
How are you practicing self care while self isolating?
JH: calling friends and loved ones, letting go of expectations, meditating,
BO: Though social distancing has put a hold on all events, I’ve been busier than ever. I’ve found that staying productive has been a great source of tranquility for me. My entertainment work at Fireplay has pivoted significantly in challenging and exciting ways. I’ve started new workout routines, filled my weekends with home improvement projects and in general have been making an effort to create every day, even if it’s a quick sketch of a house plant.
CF: I'm taking this downtime to really get healthy in all the ways I can; eating very cleanly, reading every day, exercising, taking long walks. I'm just trying to learn and stay active. It's very easy to give in to laziness right now. I've been slowly updating my website and portfolio. It's a process that often takes me days, but since I've no current due date or future work, I'm really taking my time. I'm lucky to be isolated with my girlfriend, so we're watching some TV before dinner, and a movie at night before bed.
PK: Right now I am trying to launch a second business, so it’s been looking to find a balance between keeping Sigil day-to-day and long-term strategy tight while concurrently fleshing out new strategies for the back half of 2020. Somewhere in the mix, a giant green salad, a smoothie, a bath. Lots of wine. Lots of baths. Listening to my inner dialogue, noticing, journaling. These things all help. With heaps of social calls.
BMG: I’m taking this time to sleep and rest as much as possible. Washing my hands and sanitizing everything of course. I’ve been going on jogs and trying to maintain a normal diet as well. Freaking out is never a good idea, and I somehow don’t often.
MDG: I'm talking long, restorative walks to the Hudson River, and that's a practice I want to continue after self-isolating ends. I'm cooking more and taking breaks to make tea or coffee, and I find that these mundane activities––when pursued with intention and purpose––break up the day in a way that makes it feel more manageable in the rush of calls and virtual meetings. My spouse is a fitness enthusiast, and I'm constantly reminded that I don't create enough time for exercise, but I light my candles, drink my tea, pursue my skincare routine, and try to keep in contact with friends.
BA: I wake up early every day so I can squeeze as much life out of it as possible. During this time self-care has looked like connection. Any time I have the opportunity to chat with a friend or do a virtual happy hour, I'm usually very down. It helps clear my mind and remind me I'm human.
JS: Monday - Friday I still set an alarm for 7:00 am. I get up and take my one hour for myself with coffee (always with coffee). I then answer pertinent emails and work out, whether it be running or some light weight training with the equipment I have here. I then work on different projects trying to stay busy. A lot of what I am doing right now is strategizing for the future. Around mid-day I shower and "get ready" for the day. I figure this is the only time in life where I will be able to get ready at noon without some serious judgment (self or otherwise) so I am taking advantage of it.
What does self care look like in a “normal” weekly routine?
CF: In a "normal" routine, I'm constantly on the go. I have a weekly street style column for a website called Grailed, so I spend hours
MDG: I think it's important to do what we can to take care of ourselves and advance our interests and not feel overburdened by what we can't manage right now. Even if time is bleeding together, you do have to shut the laptop eventually, unplug, and let whatever happens next happen tomorrow.
