5 Tips To Break Entrepreneurial Isolation

Advice from your peers to inspire change.

Being your own boss comes with tons of perks and zero structure. When you set out on your own to call all the shots, you didn’t anticipate missing the social rituals associated with working a 9–5 — lunch with co-workers, cooler gossip, the 4pm sugar and caffeine fix and so on. Well, maybe you don’t miss it that much, considering you went out on your own. What you may miss is the socialization structure of a fixed job.

Photo courtesy of Unsplash

Setting out on your own is impressive, daunting and exciting. When you swap out the security of a corporate gig, you don’t think about how your day will actually play out.

I’ve been working for myself as a Brand Strategist and copywriter for the past five years and previously lived the go, go, get it to air, 24/7 life of a TV news producer. What I never anticipated was how challenging it would be to constantly be alone — and I actually enjoy alone time. The time I used to value can often feel isolating. Personally, I’m not into co-working spaces as I find them to be the antithesis of social.

“What you seek is seeking you.” Rumi

So how do you re-connect? Studies show loneliness can be detrimental to your health and working alone can lead to depression.

I spoke with some of my successful entrepreneur peers to see how they break the isolation finding balance and social connectivity.

Hopefully their tips and takeaways will help you find a new rhythm to your day. (I’ve included my own, as well.)


1. Schedule Your Life

Samantha Harris, Brand Strategist + Copywriter

“Personally I love the flexibility of working for myself, but need structure. I have a relatively consistent routine daily but need three factors to play into my day for me to feel fulfilled/accomplished. I set goals for the day, mark them off my list, dedicate 6hrs to solid work, make time to workout and coordinate a social lunch or dinner with a friend and date nights with my love. As my workload ebbs and flows, so does my day-to-day, knowing that there will be highs and lows helps me stay productive on days when my workload is lighter I fill in my time with workshops, lectures or taking the time to learn something new that will broaden my knowledge base.

Lauren Stern, Interior Designer

”I have a daily schedule that keeps me organized and ensures I fit in everything (and don’t forget anything)! I have about 6 hours per day to work, which I split between my office and traveling to project sites and maker studios. I find tremendous benefit of in-person meetings because they are when the best ideas happen.

Here’s a rundown of my day, 7 am — 8:30 am — Feed my family and get them off to school / work. 8:30–11:30 — Office work: admin, uninterrupted designing. 11:30–2:30 — Out of office work: meetings with contractors, vendors, furniture and product designers. I work on many residential renovations, and it is important for me to closely monitor construction progress. The best ideas always come together on the project sites and in meetings at furniture, upholstery or lighting studios. There is collaboration between designers, architects, contractors, makers and clients — everyone has a different perspective that contributes to the best-made and most functional design. 3:00 — I pick up my daughter from school and we spend the afternoon together.”

DJ G.Brown, Music Producer, DJ, Entrepreneur

“I think the key to balance is to create a routine, especially starting off your day (before starting work) that focuses on your physical and mental well being. I like to meditate, do yoga or exercise and have a nice meal before starting my workday. That grounds me, clears my head and puts me in the right mental space to take on the world.

Beyond that, I try to limit my time working per day to around 6–7 hours and do my best to eliminate all possible distractions in order to hit that mark. It’s easy to get caught up in the “work from when you wake up till you fall asleep” pattern, but that’s not healthy (physically, mentally or romantically). Best to set a time limit to the amount of hours you want to work. There will always be time tomorrow to finish what you didn’t get done today. 6 hours may not sound like much to most people, but I don’t approach those 6 hours like someone who’s working for someone else, taking breaks, chatting with co-workers, etc. I’m talking about 6 hours of intense, unbroken concentration of what I’m doing.

You’d be amazed at how much you can get done when working like that. I have also gotten out of the habit of going on social media, especially time-consuming platforms like Facebook.

Beth Gutierrez, Owner, Joy Culture Events

“Establishing a morning routine: For me, this means getting up at about the same time every day, reading through emails while I eat breakfast, working out (outside of the house), showering and then getting on with the business of work. I like to vary my day after that, though, so it doesn’t feel monotonous.

Getting dressed is crucial, I’m sure there are many people who can feel productive in their jammies, but I’m not one of them. No matter how much I get done, I don’t feel like I’ve accomplished anything if I stay in comfy clothes all day and don’t even run a comb through my hair.”

2. Co-Work By Choice

Cyndie Spiegel, Speaker and Business Strategy Coach

“Co-working “by choice” with only people that give you energy: I stay motivated by tapping into my local solopreneur + founder friends to co-work in our neighborhood either at our apartments or local cafes. Getting dressed and getting out is a MUST! If one of us can’t co-work based on workload, we’ll schedule a lunch or coffee date with ZERO work instead, to clear our heads.”

DJ G.Brown, Music Producer, DJ, Entrepreneur

“I think it’s also important to not limit yourself to only working in your home/office. Find creative ways to do your work in unconventional places/environments. It keeps things interesting, and opens the door to you to encountering new people from all walks of life, which can also provide inspiration and/or opportunities.”

Beth Gutierrez, Owner, Joy Culture Events

“Not working from home, at least not for entire days on end, maybe one full day, but never more than that in a row. I go work at coffee shops or the library so I’m out among other people — even if I never interact with them. Working from home too many days in a row gives me low-grade depression.”

3. Find Balance and Mindfulness

Erica Dunn, Reiki Master and Brand Strategist

“Working from home has definitely given me more opportunities to practice mindfulness throughout the day. I will often take breaks throughout the day to meditate making space for clarity and focus. I will sit in a different room, away from my desk and computer to meditate for 20 minutes. Another way that I practice mindfulness when working from home is by simply cooking lunch. I often take the opportunity to cook a balanced lunch and is a great way to give myself a little break, away from emails and focus on something that is totally enjoyable, relaxing and fulfilling.”

Shannon Arens, Holistic Health Coach

“I make sure that I block off some alone time. Even if it’s 20–30 minutes where I can just do whatever I want. Some of my favorites: yoga, drinking tea and reading a book, or even just going for a walk outside.

I try my best to turn off all devices and just be with myself. It’s the only way I can recharge and give my all to my business. Eating whole foods that won’t cause that spike in energy followed by a crash is so important as well. I avoid sugary foods and refined carbs and eat lots of leafy greens, veggies, whole-grains and lean proteins. This keeps my energy up throughout the day, which is vital when you are running your business on your own and wearing all of the hats!

Suzanna Hendricks, Co-Founder, Little Voices are Loud

“For me it’s always about the tribe around me, and being willing to step away to find balance. Taking quarterly solo retreats and building in infrastructure for wellness. Knowing that there is always more I can and could do, balancing both the hustle and wellness. Surrounding myself with friends and leaders who are in varying sectors of culture to continue getting outside perspective!

4. Get Social!

Danya Shults, Founder, ARQ

“The loneliness shows up most when I’m missing collaborative brainstorming. I turn to communities like Dreamers and Doers and I have what I call a kitchen cabinet, which is an informal, revolving cast of advisors whom I know I can grab coffee with or hop on the phone with to get tactical advice or feedback or just brainstorm with. I also have a monthly supper club with a group of women from college — two key things I can count on.”

Danielle Rothman, Owner Rothbyrns Creative

“I’ve joined very supportive Facebook groups and Instagram pods and sought out opportunities to meet people in real life who do what I do. I love my Facebook groups because not only do I get great advice, but also I’m able to give advice and reflect on how far I’ve come in a short time. I also try to attend workshops and events led by people I admire so that I can establish connections and (hopefully) mentoring relationships.”

DJ G.Brown, Music Producer, DJ, Entrepreneur

“Since we often work alone, it’s so vital to get face to face interactions with people throughout the week. It helps keep us grounded, as well as gives us some time to think about something other than our work, and, of course, opens the door to new thoughts and ideas. I am not one for small talk or gossip, so I choose to keep company with other people who are about deep, meaningful conversations. I often find inspiration just from these conversations with friends.”

Beth Gutierrez, Owner, Joy Culture Events

“Breaking up the day: I try to schedule things that will help break up my day and give me an opportunity to get out and about, whether that’s meeting with a potential vendor partner over coffee, grabbing lunch with a friend, jumping on a webinar or running a few quick errands. I’ve recently started considering blocking out a day or half day every few weeks to simply explore and be inspired — and get out of the house!

5. Read for fun + Listen to Inspiring Podcasts

Erin Tarr, Confidence and Communication Coach at Be The Benchmark

“When I truly decided that I wanted to embark upon this entrepreneurial journey, listening to podcasts that would keep me motivated and inspired became my total go to tool! These podcasts remind me that I’m not crazy to be starting something new, and I’m not alone in this world even if I sometimes feel alone in my own community.”

Check out Erin’s podcast picks <> Dave Ramsey’s Entreleadership <> Gimlet’s Start Up <> This is Your Life with Michael Hyatt

Cyndie Spiegel, Speaker and Business Strategy Coach

“Depending on what I need (quiet or inspiration); I listen to audio books and read chapters from books that uplift me especially before bed and when I wake up. For example, Pema Chodron or Danielle Steele. No kidding because some days we don’t need to think!”


Follow these suggestions and plan your day, week, or month according to what you need. I wholeheartedly guarantee if you incorporate at least one of these tips into your routine it will help you break out of the isolation entrepreneurship can often cause.

If you have tips of your own please tweet them at me! @frreshsamantha

Top 5 Takeaways
1. Plan your day + get dressed
2. Set aside six solid hours to focus on work
3. Get out and work with friends or in new environments
4. Make time for mindfulness
5. Get social — join a community IRL or online