When times are good it’s easy to feel like entrepreneurship is the only path for you, but what about the times when your hit with multiple crises at once? We wondered if all entrepreneurs have moments when they wonder whether they should have gone with (or stuck to) a more standard job where they worked for someone else.

Tamya Bell

The life of a business owner is a mix of joy, challenges, and moments of reflection. Most days, I feel incredibly grateful to wake up and pour my energy into something that’s mine. But, sometimes I do wish i could go back to a 9-to-5. I sometimes wish i was still a teacher. One of those moments happened not too long ago. In october, I turned 24 and the week of and before my birthday had been a whirlwind—balancing my cosmetology classes, responding to clients, creating content, and prepping for a weekend shift at the salon. On top of that, I had a idea to start my podcast Infused With Melanin. I had to choose between staying up late to get it done or postponing my own plans. My cat was curled up next to me, purring softly, which was comforting, but I still felt overwhelmed. Read more>>

Gaston Kaufer Barbe

As a business owner, I find immense satisfaction in building something meaningful and making an impact, but I’d be lying if I said I never reflect on what life would be like with a traditional job. One such moment came after a particularly long day of juggling client demands, managing my team, and dealing with unforeseen challenges. The weight of responsibility was overwhelming, and I wondered if a regular job—with fewer variables and more predictable hours—would feel less stressful. However, as I reflected, I realized that while a regular job might offer stability, it wouldn’t provide the same sense of fulfillment I get from solving complex problems, driving innovation, and creating opportunities for others. I concluded that the challenges of entrepreneurship, while daunting at times, are deeply rewarding because they align with my passion for growth and making a difference. That perspective helps me navigate tough days with renewed purpose. Read more>>

Gabriel Felipe Osorio

I’ve experienced both sides, and for me, entrepreneurship is infinitely more rewarding. When I began my entrepreneurial journey, I was on my own—figuring out everything. Marketing, sales, operations, finance, management—you name it. That experience alone accelerated my knowledge and deepened my passion for business. I spent countless hours reading, networking, researching, building websites, crafting content, launching marketing campaigns, and managing finances. But you might wonder: Why would anyone choose to work 14+ hours a day? What’s the motivator? How could that possibly be fulfilling? Here’s the thing: as an international college student with limited work hours (20 hours a week at $8/hour), financial instability was my reality. My soccer scholarship covered tuition, and my family helped with some expenses, but I was barely scraping by—capped at a mere $600/month. That’s when the existential questions hit: Why is someone else deciding how much my time is worth? Who made that rule, and why am I abiding by it? Read more>>

Lily Fox

Yes to both. I do sometimes wonder what my life would be like if I had a regular job. I think about the structured work hours, predictable responsibilities, and consistent salary and benefits. But when I reflect on those things, I realize they don’t appeal to me the same way my current role does. The truth is, I enjoy having a lot of responsibilities and the fast-paced, creative work that comes with leading a nonprofit. Yes, my hours are unstructured, my compensation is less stable, and the work can be unpredictable, but these challenges energize me. They make every success feel earned and meaningful, and I wouldn’t trade that for predictability. Read more>>

River Dantzler

As someone who has held all kinds of different jobs working for other people over the years, it was a big shift to jump head-first into owning my own business. Last year I was working as a housekeeper in the morning and waiting tables in the evening, and my body was really paying the price. After injuring myself at work and realizing I wasn’t taking my chronic health condition seriously, I finally called it quits. With the help of my partner, I took a break from work and then re-evaluated what my work life could look like. I’ve always loved creative expression, so it came pretty naturally to look at how I could use my creative skills to create a healthier life for myself. Now, I’m so grateful to have the freedom and flexibility to prioritize my health when I need to. I love working for myself and making my own decisions about my work life. Even though it can be stressful, I’m much happier as a business owner than I was as someone’s employee. Read more>>

Lia Cohen

Being a business owner sounds so romantic at first. People often imagine it as a way to escape the 9-to-5 grind, with more freedom and time. But the reality isn’t quite like that—it’s not passive at all, and a lot depends on how you’re financing your business. In my case, it’s all self-investment, which means I’m usually the last to get paid. Sometimes, all I wish for is an extra day in the week just to catch my breath and recharge. But that’s not how it works when you’re building something from the ground up. Sure, there are moments when I dream of the simplicity of getting a paycheck at the end of the month, closing the office door behind me, and leaving the responsibilities with someone else. But then I look at what we’ve achieved so far and all the possibilities ahead—and it makes the challenges worth it. I’m deeply empathetic by nature, and seeing my team (we call ourselves THE LADY TEAM) grow and thrive, both personally and professionally, is incredibly fulfilling. That’s the real reward for me—it’s what keeps me going. Read more>>

Ali Sullivan

Being a business owner definitely has its ups and downs, but overall, I love it. I get to be my own boss, make my own hours, and decide who I work with and when. That kind of freedom was one of my main goals when I started, and it’s something I value deeply. But it’s not without challenges—taking full responsibility and staying disciplined took some time to adjust to after having regular jobs. After the pandemic hit, I realized how important it was to rely on myself. Starting my own business felt like a butterfly effect—I made a choice, took a leap, and it changed my life. It’s not just work for me; it’s a lifestyle that aligns with my values of freedom, creativity, and independence. Read more>>

Edna Sims

I am glad I am a business owner; there are no other options for me. Every morning that I wake up, I thank God for what I do. I have worked a nine-to-five job, and I was unhappy. Never do I wonder what it would be like to have a regular job. Read more>>

Isabella Doherty

Am I happier as a business owner? Absolutely. But let’s be real—it’s not always easy. There are moments, like when a client decides to leave and a chunk of my income goes away, and every once in a while I catch myself thinking, wouldn’t it be simpler to just have a steady 9-to-5? That thought doesn’t last long, though because my mom has always taught me to be someone who loves taking risks. Growing up, I was the kid who tried out for competitive cheerleading, went for the solo in choir, and just went for it—even when the odds weren’t in my favor. That mindset drives me as a business owner. If I lose a client, I know I can bounce back and find another—or maybe three if I’m feeling ambitious. Read more>>

Rachel Goad

I love being a business owner — of course there are drawbacks (such as having to provide your own benefits like health insurance and paid time off), but I love having so few obstacles between vision and execution. What I mean is: if I have an idea for my business, I can implement it straightaway without going through an office hierarchy, funding proposals, or approval delays. I love having a direct relationship with the consequences (good and bad) of my own decisions, and having a direct relationship with clientele. Not only have I had the privilege of becoming better immersed in my community, but in this line of work, every dog walk is an opportunity to network, an opportunity to self-market, and an opportunity to meet your next client (or even your next business partner or business affiliate). Especially in Annapolis and Eastport, which are not only incredibly pet-friendly places, but communities that fervently and earnestly support small businesses. Read more>>

Kim Hernandez

My story of entrepreneurship is quite different from most because after I dropped out of college, (due to health reasons) I walked into entrepreneurship and never had a regular 9-5 job in my life. Many might hear that and think, “that’s the dream” but being a business owner is very challenging and is definitely not for everyone. I started my journey with fashion reselling on sites such as eBay and Poshmark. I transitioned into creating my own products such as positive affirmation t-shirts on Etsy. Lastly and more recently I launched a Christian clothing brand “About God Shop.” In the beginning of my journey I didn’t think much about having a regular job because my health didn’t allow for it. I was being treated for hyperthyroidism that then turned into hypothyroidism after radiation treatment. Fashion reselling was part time work that I would do while I was navigating my sickness and recovering. Read more>>

Katherine Avila

I can genuinely say I am happier as a business owner. Having a regular has not been in my plans for so long, but I’ve had seasons where I had no choice but to get a regular job. I’ve never been happy at the jobs I worked because they were never jobs I was passionate about. Doing hair is my happy place. It allows me to be creative, make my own schedule and I simply enjoy it. I love making others feel better about themselves and seeing my work come to life and just get better each time. Read more>>