Episode Summary:
Working solo sounds amazing until you realize just how tricky it can be to keep yourself on track. Freedom of schedule can quickly feel like chaos, the quiet of home can get a little too quiet, and without a team there’s no one to lean on when things get heavy. In this conversation, I’m talking about the challenges we face as solo entrepreneurs, the structure that actually helps me stay focused, and the simple slump-busters I turn to when the loneliness and doubt creep in.
What I hope you take away from today's episode...
- The same freedoms that drew you to working solo can also become your biggest challenges
- A little structure and a few simple rituals go a long way in keeping you grounded
- Slumps are normal, but they don’t have to derail your whole week
- Community matters, even when you’re building something on your own
- You can keep showing up for your business without burning yourself out
Links to connect with me...
Book a Consult HERE! (https://caffeinecreative.io/consult/)
Email me HERE! theperfectblendcaffeinecreative.io
Find me on Substack!
Detailed Show Notes
(automatically transcribed using AI Technology)
She thought I "had it all figured out!"
Last week, I was talking to a new connection and we were having a fabulous conversation about life and being a solo entrepreneur and all the things that come with it. At one point, this beautiful woman in front of me said, “You just seem like you’ve got it all together, like this business thing is always so easy for you.” In that moment, everything kind of stopped for me.
Honestly, my jaw may have fallen open because there are plenty of times over the year where I feel the complete opposite. I feel like I don’t have this figured out, that I don’t know what I’m doing, that I don’t know what direction to go, and the doubts and insecurities start to feel insurmountable. While those moments come a little less often the longer I do this solo entrepreneur thing, they still happen, and they can be intense. In fact, this week was one of those moments.
Being a solo entrepreneur is not for the faint of heart.
It takes courage, determination, and a whole lot of ingenuity to make it all happen. And sometimes, when you’re trying to do all three while no one else is around to hold you accountable, it can feel like too much.
So today I’m sharing how I keep going when the overwhelm and the loneliness of solo entrepreneurship feels like too much. We’re going to look at the challenges, the things I do to overcome them, and the ways I shake off the solo slump when going it alone feels just a little too lonely. But before we dive in, a quick intro if you’re new here.
I am Teresa Schlup, the Original Caffeine Creative. By day, I’m a brand strategist and web designer. I work with other solo entrepreneurs in service-based businesses who want to stand out and be real, authentic, genuine. Fill in whatever word feels good to you. That’s what I do, and I love what I do, even in the weeks when it feels a little too lonely or a little too challenging.
If you’re looking for a brand strategist or web designer, I’d love to talk. Head over to caffeinecreative.io and book a consult so we can talk about how you can stand out in your field. Now, on to today’s episode.
The Challenges of Being a Solo Entrepreneur
Interestingly, some of these challenges were what enticed me to go the solo route in the first place. The first one is the freedom in a schedule. When I started this journey way back in 2011, I still had kids at home, three kids who were very, very active. I was wrangling a whole bunch of schedules to manage everything as a family.
Challenge #1: The idea of a flexible schedule
Working when I wanted to, taking time off more easily, adjusting around my kids was really enticing. I had a fabulous boss who let me have time off for my family, but I still had to put in that 40-hour week and balance everything. That got overwhelming, so the freedom of schedule pulled me toward solo entrepreneurship.
Then I became a solo entrepreneur and started working from home and realized that freedom of schedule was more of a hindrance than I expected. Sure, I could work at midnight, 3 a.m., or noon. I could set my own hours. But constantly shifting my work hours created chaos, not productivity. Freedom of schedule is enticing, but challenging.
Challenge #2: The blurry line between home and work life
This is especially when you work from home. Back then I worked from my kitchen table, or wherever there was a clean spot. It’s hard to focus on the task at hand when you see the laundry, the dishes, the overflowing trash, the dog that needs a potty break. You get the idea. Work–life balance gets tricky when your office is your home.
It’s also challenging to stay motivated when you know nobody is watching. In a corporate office, accountability is built in. You naturally want to show the best version of yourself. When you work alone, whether from home or an office, there’s no one to impress. That can make motivation harder when no one cares how busy you look in the moment.
Challenge #3: Working in Isolation
There’s no camaraderie and no healthy interruptions. In the office, there were natural interruptions. They drove me crazy at the time, but they were healthy. They made me stop and move around, stretch, go to the bathroom, reset my brain. At home, I don’t have those interruptions. My dogs and cats know when Mommy’s working, leave her alone. If I’m not careful, I park in my chair for hours and suddenly it’s three o’clock and I haven’t moved, eaten, or done anything. That never feels good. I miss those natural breaks and the camaraderie. The “Hey, you’ve been at it a while, let’s take a walk or grab a coffee.”
Challenge #4: No Team standing beside you
In a team, someone can take on part of the checklist when you’re overwhelmed. You can bounce ideas around. Someone stands beside you through the tough things and celebrates the wins. As a solo entrepreneur, you don’t have that. As much as my dogs love me and celebrate pretty much anything, it isn’t the same as having people who get it and are in it with you.
How I Overcome the Challenges
Step #1: Create a Set Schedule
The first thing I did was set a schedule. I start and end at about the same time each day, with a little wiggle room, but having consistent work hours helps my brain shift into work mode and stay there. If I want to take a day off, I plan ahead and spread those hours across the rest of my week, just like I did when I worked for someone else. And if I put in extra hours, I balance them out later.
Along with a schedule, I’ve built rituals. When I worked outside the home, I had natural cues, like the drive to work. Now, I’ve created my own. Feeding the animals, making my breakfast, and sitting down at my desk signals the start of my day. Checking email around 3 p.m. signals that it’s time to wrap up. These little rituals help my brain shift gears.
Step #2: Time Blocks that Align with My Strengths
I also love working in time blocks aligned with my strengths. I’m sharper and more creative in the morning, so I avoid morning meetings when I can. I save afternoons for admin, meetings, and planning things that don’t require peak creativity. Time blocking can work if you align it with your natural rhythm. Maybe you’re a night owl like my sister and do your best creative work later. There’s no universal method. Experiment, be honest about what works, and adjust.
Step #3: balancing productivity, creativity, movement, and reflection each day.
Balance doesn’t mean equal time. Some days need more productivity; other days need more creativity. Sometimes movement supports me best; other times I need time for reflection. Thinking about where my business is going, what’s working, and what to tweak. I try to include all four daily, in shifting amounts. It keeps my mind sharp and focused and makes the work feel both effective and enjoyable.
Step #4: Get a Sounding Board
I make sure I have other entrepreneurs I can reach out to, people I can jump on Zoom with, Voxer, or text when I need a sounding board. Ideally, they understand business, share my values, and I respect their opinion. This can be one-on-one or a mastermind. It doesn’t have to be formal. No agendas or minutes, just real conversations. I meet with a small group of ladies every other Thursday. When we miss a couple of sessions, we really feel it. Having people who get it is invaluable in this journey, and your pets can’t replace that.
Step #5: Set Clear Boundaries
When you work from home, especially without a dedicated office, lines blur. People in your home see “home you,” not “work you.” It’s on us to set boundaries through open communication: share your work hours, ask for a distraction-free workspace during those hours, and explain how they can support you. It may take a few conversations, but when you communicate respectfully, people start to understand and give you the space you need. Boundaries pair naturally with the set schedule, be present when you need to be, and make sure the people around you know when that is.
even the best laid plans often go awry.
You can create boundaries, structure your day, tap into your strengths, and balance all the pieces, and you’ll still have days or weeks when doubt and worry take center stage. Times when you feel overwhelmed, when you question whether this was a good idea, when you wonder if anyone even wants to work with you. The longer I do this, the less often it happens, but it still happens. This week was one of those weeks.
Despite following my schedule, honoring my boundaries, aligning with my strengths, and checking all the boxes, my brain wasn’t keeping up. I was in the slump: lonely, isolated, and wondering if any of this matters.
So what do you do then? It’s time to shake things up. I have a lot of approaches, sometimes I do all of them; sometimes one is all I need.
First, I stick to my rituals with extra intention. I make sure I start on time, do my little pre-work routine (feed the dogs, play with the pups), and end on time. Sometimes all it takes is honoring the routine.
If that doesn’t work, I set a timer and focus on winnable tasks. Ten, twenty, or forty minutes, whatever you choose, then knock out quick items that are looming. Be strategic: pick tasks you can finish fast. Those quick wins can shift your energy and remind you that you’re capable and productive.
If I’m still stuck, I clean and organize my office for twenty minutes. I’ll go through the mail pile, dust my desk, water plants, clean windows, whatever fits the timer. Pouring a little love into my workspace helps me remember why I love what I do and often snaps me back into focus.
If that still doesn’t lift the slump, I reach out to my sounding boards. I call someone or send a Voxer/voice text, because it feels like a real conversation and get things off my chest. They may not respond immediately, and that’s okay. Knowing someone has heard me creates a shift.
If I’m still stuck, I have two quick fixes and two that take a bit more planning.
Quick fixes:
- Move. Take a walk, dance to a favorite song, drop for ten pushups. Something... Anything... to get blood flowing and creativity going. Getting outside is powerful. A ten-minute walk around my acreage, checking wildflowers or hummingbird feeders, can change everything. In South Dakota the weather doesn’t always cooperate and I hate the cold, so I’ll dance, do a short workout, or hop on the treadmill.
- Do a 60-second gratitude exercise. Set a timer, grab a notepad, and brain-dump everything you’re grateful for. Ideally business-focused, but don’t overthink it. I used this back in my life-coaching days and in my corporate office. I would tell everyone to ignore the phones for 60 seconds and write. It always shifts the mood.
The two fixes that take a little planning:
- Change of scenery. Go work somewhere else for the day. Yesterday I went to a local coffee shop to work on a client marketing plan, strategy and outlining with a blueberry muffin and a hazelnut latte. I left feeling energized, focused, and accomplished. Try a co-working space or a park with a hotspot. Whatever works for you.
- Schedule a day off and plan something fun. Sometimes we’re so head-down we forget to play. A couple of weeks ago, I got a massage, took myself to lunch, walked one of my favorite spots in Sioux Falls, and met my daughter for drinks after work. I stayed off my phone and didn’t think about work. I ended the day feeling amazing.
Those are the things that help me shift out of a slump and stay motivated, focused, and on top of the business I’m building. If you have ideas I didn’t share, I’d love to hear from you! Message me, email me, text me, or drop a comment wherever you’re listening.
Have a great week, and I’ll see you next time.
