Ian Wiedenman blog

I grew my company ITW Creative Works from a start-up to a thriving creative development agency through strategic business growth and strong client relationships.

The Journey of a Solopreneur: Lessons from Expanding to Multiple Projects

The Journey of a Solopreneur: Lessons from Expanding to Multiple Projects
Entrepreneurship Business Growth Personal Development 10 min read 11 comments

Discover how Ian Wiedenman evolved from launching a single project to managing multiple innovative ventures, sharing valuable lessons and future aspirations along the way.


From One to Many: My Solopreneur Journey

When I first dipped my toes into the entrepreneurial waters, I had no idea where it would lead. Back then, Somiibo was my singular focus, my baby, and boy, was I naïve! The thrill of building something from scratch, the late nights fueled by caffeine and sheer determination—it was all so gloriously chaotic. Fast forward a few years, and here I am, juggling multiple projects like a circus performer with too many flaming torches. But let’s rewind a bit and explore how I got here.

Starting Somiibo was like strapping myself into a rollercoaster without reading the safety manual. I had a vision, a rough sketch of what I wanted to create, and a lot of enthusiasm. And trust me, enthusiasm is great, but it doesn’t pay the bills. There were moments of doubt, times when I questioned my sanity for diving into the solopreneur life. But every time I saw a user benefiting from Somiibo, it reignited my passion. It was like a little nudge from the universe saying, “Keep going, Ian!”

As Somiibo gained traction, my confidence grew. I began to think, “Hey, if I can do this once, why not again?” Enter Slapform.com and StudyMonkey.ai, the next chapters in my ever-growing book of solopreneurship. Transitioning from one project to multiple wasn’t a walk in the park. It felt more like running a marathon while juggling and occasionally dodging obstacles thrown my way. But the learning curve was steep and exhilarating.

Each new project came with its own set of challenges and rewards. Slapform.com was an adventure in user experience and design, while StudyMonkey.ai plunged me into the fascinating world of AI. The diversity kept things interesting, and I found myself constantly learning, adapting, and evolving. It wasn’t just about expanding my business; it was about expanding my horizons.

Of course, the journey hasn’t been all smooth sailing. There have been sleepless nights, countless cups of coffee, and moments of sheer panic. But there have also been victories, both big and small, that made it all worthwhile. From securing my first users to getting positive feedback, each milestone has been a testament to the hard work and dedication poured into these projects.

Looking back, the transition from focusing on a single project to managing multiple ones was a turning point. It taught me resilience, the importance of time management, and the art of balancing multiple hats. And while I sometimes feel like I’m on a never-ending treadmill, the journey has been incredibly rewarding.

Stay tuned as I dive deeper into the challenges, key lessons, and future plans in the next sections of this journey. And remember, if you’re ever contemplating the solopreneur path, buckle up—it’s one heck of a ride!

The Challenges: Balancing Multiple Projects

Balancing multiple projects as a solopreneur can be quite the juggling act! At first, it feels like you’re a kid in a candy store—so many ideas, so much potential. But soon, reality sets in, and you realize you’re not just sampling sweets. You’re running the entire candy shop, from stocking shelves to managing sales. The challenges? Oh boy, where do I start?

First off, time management. If you think managing one business is tough, try managing several. Suddenly, 24 hours in a day seem woefully insufficient. One minute, you’re tweaking a feature on Somiibo, and the next, you’re dealing with a customer inquiry on Slapform.com. It feels like playing whack-a-mole, except the moles are deadlines, and they just keep multiplying.

And let’s not even get started on the mental gymnastics. Switching gears between projects can be mentally exhausting. Each project has its own set of priorities, deadlines, and challenges. It’s like having multiple tabs open in your brain browser—each one demanding your attention. Some days, I swear my brain feels like it’s running on dial-up.

Then there’s the issue of resources, or rather, the lack thereof. As a solopreneur, you’re often the CEO, the marketer, the developer, and the customer service rep all rolled into one. The pressure to wear so many hats can be overwhelming. You’re constantly asking yourself, “Should I focus on marketing StudyMonkey.ai today, or should I debug that pesky issue on Slapform.com?” It’s a never-ending game of prioritization.

But perhaps the most significant challenge is maintaining a work-life balance. With so many projects on the go, it’s easy to let work consume your life. Weekends? What are those? Evenings? Those are just extra hours to get stuff done. Before you know it, you’re burning the midnight oil more often than not, and your personal life starts to take a back seat.

Despite all these challenges, there’s a silver lining. Each struggle teaches you something invaluable. For instance, I’ve learned the importance of setting realistic goals and sticking to them. I also discovered the power of delegation—yes, even solopreneurs can delegate! Tools and apps have become my best friends, helping me keep track of tasks and deadlines. If you’re curious about my toolkit, check out the tools I use to manage multiple projects successfully.

In the end, balancing multiple projects is a rollercoaster ride—thrilling, challenging, and sometimes downright scary. But that’s the journey of a solopreneur, isn’t it? It’s not about avoiding the challenges; it’s about learning to dance with them. And trust me, the dance floor is never boring!

Key Lessons Learned: What Worked and What Didn’t

Navigating the choppy waters of juggling multiple projects as a solopreneur has been nothing short of exhilarating—like riding a roller coaster with no seatbelt. There have been wins, losses, and a fair share of hair-pulling moments. So, what worked and what didn’t? Let’s dive into the juicy bits.

First off, let’s talk about time management. It turns out, trying to manage multiple projects without a plan is akin to herding cats—chaotic and largely futile. I learned early on that having a structured schedule is non-negotiable. Tools like Trello and Asana became my best pals, helping me keep tabs on everything from development timelines to marketing strategies. But, here’s the kicker: flexibility. While my schedule was my guiding star, being too rigid often led to burnout. There were days when pivoting was essential, and learning to adapt was a game-changer.

Next up is delegation—or in my case, the lack thereof. One of the biggest pitfalls was my reluctance to delegate tasks. I wore my “I can do it all” badge with misplaced pride. Spoiler alert: I couldn’t. Realizing that outsourcing certain tasks could free up my time for more critical aspects of my projects was a turning point. Hiring freelance developers and virtual assistants was like discovering a hidden superpower. It allowed me to focus on what I do best: innovating and steering my ventures in the right direction.

Now, let’s chat about the importance of community. Going solo doesn’t mean going it alone. Engaging with other solopreneurs and joining online forums provided me with invaluable insights and moral support. Sharing experiences and challenges with like-minded individuals was immensely reassuring. Plus, it opened doors to collaborations and partnerships that I hadn’t considered before.

One of the most humbling lessons was embracing failure. Not every project was a roaring success, and that’s okay. Each misstep was a lesson in disguise. For instance, when StudyMonkey.ai didn’t initially gain traction, instead of throwing in the towel, I took a step back, analyzed the feedback, and made necessary adjustments. Embracing failure as a part of the journey, rather than the end of it, was liberating. It’s like that old saying—fall down seven times, get up eight.

Lastly, constant learning and adaptation were vital. The entrepreneurial landscape is ever-changing, and staying static is a surefire way to get left behind. Whether it was attending webinars, reading industry blogs, or simply experimenting with new ideas, keeping the learning curve steep was crucial. For more on my evolving process, check out From Concept to Launch: My Process for Developing New Projects.

So, what didn’t work? Trying to balance creativity and practicality without a clear strategy often led to half-baked ideas. It was a lesson in the art of balance—a topic I delve into here. Also, spreading myself too thin across too many projects diluted my focus. Diversification is essential, but so is knowing your limits. For insights on why I believe in diversification, head over to Why I Believe in Diversifying My Entrepreneurial Ventures.

In short, the journey from a single project to managing multiple ones has been a roller coaster of learning, unlearning, and relearning. It’s been a wild ride, but one that’s taught me invaluable lessons and shaped my path forward. Here’s to more projects, more lessons, and a lot more fun along the way!

Looking Forward: Future Plans and Aspirations

As I sit here with a cup of coffee, reflecting on the whirlwind that has been my journey from launching Somiibo to managing a slew of exciting new projects, I can’t help but chuckle at how far I’ve come. The ride has been wild, with more twists and turns than a roller coaster designed by a caffeine-fueled engineer. But, oh, what a ride it’s been!

Looking ahead, I see a horizon brimming with opportunities and, let’s be honest, a fair share of challenges. The goal isn’t just to expand for the sake of expansion but to create meaningful, innovative solutions that resonate with real needs. Somiibo was the spark, and projects like Slapform.com and StudyMonkey.ai are the flames that continue to light my path.

One of my primary aspirations is to dive deeper into the realm of artificial intelligence. StudyMonkey.ai was just the beginning. The potential of AI to revolutionize how we learn, work, and even play is mind-boggling. I envision a future where AI isn’t just a tool but a collaborator in our daily lives. Imagine personalized learning experiences, AI-driven business insights, and even creative projects co-authored by algorithms—sounds like sci-fi, but we’re inching closer every day.

Of course, technology will play a crucial role in scaling these ventures. I’ve learned a great deal about leveraging tech to streamline operations and enhance productivity. If you want a deep dive into how I do this, check out my blog post on how I leverage technology to scale my projects efficiently. Trust me, it’s a game-changer.

Another exciting frontier is community building. I’ve always believed that behind every successful project is a vibrant, engaged community. Whether it’s through interactive platforms, social media, or good old-fashioned meetups, fostering a sense of belonging and collaboration is key. It’s not just about building a user base; it’s about creating a tribe of passionate individuals who share the journey.

But hey, it’s not all smooth sailing. Balancing multiple projects is no walk in the park. It requires impeccable time management, a knack for prioritizing, and, sometimes, the ability to laugh in the face of chaos. If you’re curious about how I juggle it all, you might find some nuggets of wisdom in my post on staying focused while juggling multiple projects.

Looking forward, I also aspire to give back more. Whether through mentorship, sharing my experiences, or supporting budding solopreneurs, I want to be a part of the ecosystem that nurtures the next wave of innovators. After all, it’s a big world out there, and there’s plenty of room for all of us to grow and thrive.

So, what’s next? Well, stay tuned! The journey of a solopreneur is never truly finished. There are always new horizons to explore, new challenges to conquer, and new stories to write. And I can’t wait to share every step of the way with you all.

Got any wild ideas or just want to chat about the solopreneur life? Hit me up! Let’s keep this adventure going.

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Follow my journey as a solopreneur, and my evolution from launching Somiibo, a single project, to expanding my empire with multiple innovative projects like Slapform.com, StudyMonkey.ai, and more