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.

How Do I Tackle the Challenges of Being a Multi-Project Entrepreneur?

How Do I Tackle the Challenges of Being a Multi-Project Entrepreneur?
Entrepreneurship Business Management Personal Development 9 min read 3 comments

Learn how Ian Wiedenman navigates the complexities of managing multiple entrepreneurial projects, offering insights and strategies for aspiring multi-project entrepreneurs.

Introduction: My Journey from Somiibo to a Multi-Project Empire

Hey there! Ever wonder what it’s like to juggle more projects than a circus clown has balls? Me too! Well, actually, I don’t just wonder; I live it every single day. My name’s Ian Wiedenman, and my entrepreneurial journey kicked off with Somiibo, my digital baby that grew up faster than I could say “startup.” But Somiibo was just the beginning, the spark that ignited a wildfire of creativity and ambition. From there, I branched out into new ventures like Slapform.com and StudyMonkey.ai, turning my solo gig into a bustling empire of innovation and sleepless nights.

When I first launched Somiibo, it felt like jumping off a cliff and building a plane on the way down. Somiibo was a social media automation platform designed to make life easier for influencers and marketers. Little did I know, it would also lay the foundation for my multi-project escapades. As Somiibo gained traction, I realized I had a knack for identifying gaps in the market and filling them with something unique, something useful, something… well, awesome.

It wasn’t long before my brain started buzzing with new ideas, each one clamoring for attention like kids in a candy store. Slapform.com came next, a platform built to streamline web form creation. Then, StudyMonkey.ai swung into the picture, bringing AI-powered study tools to students worldwide. Each project was a new adventure, a new puzzle to solve. And let me tell you, the pieces didn’t always fit together neatly.

But that’s the thrill of being a multi-project entrepreneur, isn’t it? The chaos, the creativity, the constant challenge to outdo yourself. Sure, there were (and still are) moments when I felt like I was drowning in a sea of deadlines and to-do lists. But then there are those exhilarating moments when everything clicks, and you see your ideas come to life. Those are the moments that make it all worthwhile.

So, stick around, and I’ll share the tips and strategies I’ve picked up along the way. If you’re a fellow entrepreneur—or just someone looking to bring a little more organized chaos into your life—you’ll find plenty of nuggets of wisdom here. Plus, a fair share of my personal triumphs and facepalm-worthy blunders. Because let’s face it, no journey is complete without a few epic fails, right?

The Art of Juggling Multiple Projects: Tips and Strategies

Let’s face it, being a multi-project entrepreneur is like being a circus juggler, except instead of balls, you’re tossing around entire businesses. When you’re managing multiple ventures, there’s always a risk of dropping one. But hey, that’s part of the thrill, right? So, how do we keep all these balls in the air without losing our sanity?

First off, prioritize. Not all projects are created equal, and some will demand more of your time and energy than others. I like to start my day by identifying the top three tasks that need my immediate attention. This way, I can focus on what truly matters and avoid getting bogged down by the small stuff.

Next, get organized. I can’t stress enough the importance of having a robust system to track your progress. Whether it’s a digital tool like Trello or a good old-fashioned notebook, find a method that works for you. Personally, I use a combination of ProjectManager and sticky notes plastered all over my desk. It might look chaotic, but it keeps me on track.

Another key strategy is delegation. As much as we might like to think we can do it all, the reality is, we can’t. Surround yourself with a reliable team and empower them to take ownership of their tasks. Remember, it’s not about micromanaging but about trusting your team to deliver. If you’re looking for some more in-depth tips, this article from Entrepreneur offers great insights into effective delegation.

Time management is crucial. Block out specific times in your calendar for each project and stick to it. This prevents one project from monopolizing all your time and ensures that each venture gets the attention it deserves. I often use time-blocking techniques, and trust me, it’s a game-changer. If you need more ideas, Inc. has a great guide on managing multiple projects.

Don’t forget to take breaks. It might sound counterintuitive, but stepping away from your work can actually boost your productivity. A quick walk or a coffee break can clear your mind and help you come back with fresh perspectives. It’s something I mention often on my blog because it’s so vital.

Lastly, always be adaptable. Things won’t always go as planned, and that’s okay. Being flexible allows you to pivot when necessary and seize new opportunities as they arise. For more on adaptability, check out my thoughts here.

So there you have it, folks. Juggling multiple projects can be challenging, but with the right strategies, it’s entirely manageable. Embrace the chaos, stay organized, and most importantly, enjoy the journey. After all, what’s the point of building an empire if you’re not having fun along the way?

Overcoming Common Hurdles: Personal Experiences and Solutions

As a multi-project entrepreneur, I’ve faced my fair share of stumbling blocks. But here’s the kicker—every hurdle is just a stepping stone in disguise. Let me take you through some of the most common challenges I’ve encountered and how I’ve managed to leap over them with (mostly) grace and a sprinkle of humor.

First up, the dreaded time management conundrum. When you’re juggling multiple projects, it feels like you’re perpetually racing against the clock. I remember many a night spent brainstorming for Slapform.com, only to realize I had completely neglected my duties at StudyMonkey.ai. The trick? Prioritization and a dash of delegation. I started using project management tools to keep track of tasks. Now, I can see what needs to be done at a glance rather than getting lost in a sea of sticky notes. And when things get really tough, I remind myself that Rome wasn’t built in a day, and neither will my empire be.

Next, let’s talk about the financial rollercoaster. Investing in multiple ventures means your wallet takes quite the hit. There were times when I felt more like a money magician, trying to stretch every dollar. One particularly tough period had me questioning whether I should keep pushing forward with my new ventures or cut my losses. My solution? Diversification. By spreading my investments and not putting all my eggs in one basket, I managed to keep afloat. Plus, having multiple revenue streams means that if one project is underperforming, another can pick up the slack.

Then there’s the mental toll. Managing several projects can be mentally exhausting. Burnout is real, folks. At one point, I found myself so overwhelmed that I couldn’t even enjoy the success of my projects. That was a wake-up call. I learned the importance of self-care and setting boundaries. Now, I make sure to carve out time for myself, whether it’s a quick walk, a hobby, or just some Netflix binge-watching. You can read more about my methods for staying sane while managing multiple projects here.

Networking is another hurdle. When you’re focused on multiple projects, it’s easy to become a lone wolf. But building connections is crucial. I had to push myself out of my comfort zone, attend industry events, and engage with other entrepreneurs. These connections not only provided support but also opened doors to opportunities I hadn’t even considered.

Finally, staying innovative across different projects can be a head-scratcher. How do you keep the creative juices flowing without burning out? I found that each project can actually fuel the others. The skills and ideas from one venture often spark inspiration for another. For instance, the insights I gained from developing Somiibo have been invaluable in shaping StudyMonkey.ai. For more on how I keep the innovation flame burning, check out my detailed thoughts here.

In the end, every challenge comes with a lesson. And while the path of a multi-project entrepreneur is filled with twists and turns, it’s also incredibly rewarding. Embracing these hurdles has taught me resilience, adaptability, and the importance of a good sense of humor. So, here’s to tackling challenges head-on and celebrating every little victory along the way!

Conclusion: Embracing the Challenges and Celebrating Success

As I reflect on my journey from Somiibo to managing a bustling array of projects, one thing becomes abundantly clear: embracing the challenges is just as important as celebrating the successes. Sure, there have been sleepless nights and moments where I questioned my sanity—who hasn’t had those? But each hurdle overcome has shaped me into a more resilient, adaptable entrepreneur.

Let’s face it, juggling multiple projects isn’t for the faint of heart. It requires a balance of meticulous project management and the willingness to dive headfirst into the unknown. If there’s one nugget of wisdom I can impart, it’s this: don’t shy away from the chaos. Instead, get comfortable with it. Feel the exhilaration of tackling a problem head-on and savor the victory when you find a solution.

One of the real joys of being a multi-project entrepreneur is the sheer diversity of experiences. Each project, from StudyMonkey.ai to Slapform.com, brings its own set of challenges and triumphs. Learning to navigate these varying landscapes has not only broadened my skill set but has also kept my entrepreneurial spirit alive and kicking.

Let’s not forget the importance of celebrating each micro-success along the way. These small victories are the building blocks of larger achievements. Whether it’s launching a new feature, hitting a milestone, or simply getting positive feedback from a user, take a moment to appreciate it. These are the moments that fuel your passion and drive you forward.

For those of you on a similar path, remember: you’re not alone. The entrepreneurial community is a treasure trove of support, advice, and shared experiences. Don’t hesitate to lean on it. Engage with other solopreneurs, share your stories, and learn from theirs. You’ll find that the camaraderie can be both enlightening and comforting.

In closing, being a multi-project entrepreneur is like riding a rollercoaster. There are ups, downs, twists, and turns, but it’s one heck of a ride. Embrace every challenge, celebrate every success, and most importantly, enjoy the journey. And if you ever need a little inspiration or a sanity check, feel free to check out my other blog posts like How I Stay Inspired While Managing Multiple Ventures or Why Juggling Multiple Projects Keeps Me Motivated.

Here’s to the chaos, the triumphs, and the endless possibilities. Keep pushing forward, and who knows? Maybe one day you’ll look back and realize that the challenges were the best part of the journey.

Cheers to embracing the chaos and celebrating the success!


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