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Struggling with Business Management Decisions
#1
I’ve been managing my own business for a few years now, and while things started off smoothly, I’ve found myself struggling recently with keeping everything organized. Let me share a quick story to give some context. About a year ago, I started taking on more clients—great for growth, but it quickly became overwhelming. There was this one month where I had three big projects lined up, each with different deadlines, and somehow, in my attempt to do everything myself, I completely lost track of time. I remember one Friday afternoon getting a call from a client asking about their project delivery, and I realized I hadn’t even started on it because I had been so focused on another client’s work.
Panic set in. I pulled an all-nighter trying to get everything done, and while I managed to meet the deadline, the quality wasn’t my best. The client noticed too. After that, I decided to step back and evaluate how I was managing things. I started using spreadsheets to track deadlines and progress, but soon, even that wasn’t enough. I felt like I was spending more time on administrative tasks—tracking emails, setting reminders, updating my calendar—than on actually working on projects.

That’s when I thought about hiring someone to help, but the idea of trusting someone else with parts of my business was nerve-wracking. Would they do things the way I do? Would the clients be okay with someone else handling parts of the process? At the same time, I felt like I couldn’t continue managing everything myself without burning out. I even started looking into software solutions that might help automate or streamline the workflow. But there’s so much out there—project management tools, accounting software, CRM systems—and it’s hard to know where to start or what’s worth the investment.

So, here I am, kind of stuck in the middle. Do I invest in better management tools or take the plunge and hire someone to help? I’d love to hear how others in similar situations have navigated this because I feel like I’m at a crossroads with my business. If anyone has experience with hiring their first employee or implementing new software to improve management, I’d appreciate any insights or advice. Sometimes it feels like just keeping up with the day-to-day is a job in itself.
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#2
Hello, I totally understand where you’re coming from—it’s a tricky spot. I’ve been through something similar, and what worked for me was a combination of both: improving my management tools and slowly bringing in help when I was ready. The big thing for me was realizing that I needed to stop trying to do everything on my own.

In your case, I’d suggest starting with the software side first. It sounds like the spreadsheets you’ve been using aren’t cutting it anymore. There are a lot of tools out there that can help automate tasks like tracking deadlines, managing client communication, and even handling invoicing. That alone might take some of the pressure off without needing to bring someone else in just yet. When I was researching options, I also looked into restructuring my business legally, which made things a lot easier to manage. Setting up an LLC, for example, gave me more flexibility and peace of mind when it came to handling finances and delegating work. I found some great resources at LLCBuddy, which not only helped me with the LLC setup but also offered useful tips for managing the day-to-day.

It’s definitely not easy, but getting some structure in place before hiring might make the whole process smoother when you’re ready. From my experience, once you have a system that works, bringing someone in to handle specific tasks becomes a lot less stressful because you already know how things should run. Hope that helps!
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#3
Just wanted to chime in here, even though I’m not in the same position. I’ve seen quite a few friends who’ve started businesses go through similar struggles. What they found useful was creating a routine and sticking to it, which helped reduce the chaos. Even though everyone’s situation is different, sometimes just finding a better way to manage your time and tasks can go a long way. Best of luck with your business!
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