When the Headaches of Running a Small Business Set In
Why the way we work is fundamentally broken
It’s been a few months since I began writing about our journey at Charli. And in those few months, there have been some wonderful highs and some day-to-day headaches. It’s the typical stuff, but as an entrepreneur, I can quickly get migraines 🤕when the “paperwork” piles up. Shifting gears from innovation, strategy, and product development to the administration of running a business can be a herculean task. Yet, this is an all-too-necessary shift.
In my previous post on Why We Built Charli, I shared where the idea for Charli came from (I wanted my chief of staff back). And today, I want to dive deeper into the problem that we’re designing Charli to solve. Because it’s a big one that any business owner, freelancer, or entrepreneur is all too familiar with. I like to call it “work about work”, and it’s the stuff that creates the headaches – or in my case, the migraines 😣🤬🤯
Examples of these headaches include incorporation and governance documents, legal filings, insurance contracts, vendor proposals and agreements, payroll paperwork, payroll administration, benefits tracking, employee stock options tracking, invoicing and receivables, bills and payables, client and customer statement of works, addendums and all the other important elements that are required in running a business. It’s not all the glamour of a “startup”. It’s real businesses with very real issues on a day-to-day basis. Not keeping your corporate records organized can come back to bite you and it’s important to keep them up to date. Even in the startup world of organizing a data room for investors can be a real aggravation.
You get the picture: it’s all the stuff that induces groans and that takes away from fun work (and billable hours).
The “Work About Work” Phenomenon
People start businesses because they’re passionate about an idea, a product, or their craft, not because they’re excited to spend hours a day managing all the administrative stuff. Yet, approximately 60% of our time is spent doing “work ABOUT work”. That’s a big imbalance and it adds up to several days each workweek. That amounts to sometime upwards a month per year of lost productive time. This shouldn’t be the case, but the way we work is fundamentally broken, and a lot of time and effort is spent trying to find the golden ticket to fix this imbalance.
This problem isn’t reserved just for small businesses and startups, but it is amplified for them. Most small businesses (especially solopreneurs, freelancers or consultants) don’t have an accounting team, a legal team, dedicated project managers, and so on. Yet, these owners do have the same requirements and responsibilities to learn and manage administrative tasks carefully.
In fact, there are very significant risks and costs to your business that come up if you’re not keeping on top of certain tasks (think: missed deadlines, missed tax filings, risks to IP, lost clients, lost investors, and so on).
Software is Eating the World
“But what about all those productivity apps?” you might say.
Sure, technology has evolved dramatically over the past decade, and the dominance of cloud software has ushered in thousands of SaaS solutions ranging from productivity software to automation tools. Yet, I would argue that these solutions haven’t actually taken work away from individuals. If anything, it’s required us to learn more, do more, and pack more “stuff” into the day. It’s fueled an exhausting quest to optimize every moment of every day.
Think about it like this:
We have more apps, spreadsheets, and communication tools than ever before, yet rather than less work, they’ve amounted to more data entry, coordination, and headaches than ever before (not to mention notification 🚨🔔overload).
We have more innovative cloud-based solutions, but also more complexity in accessing documents and people who are distributed across different platforms and geographies.
We have more ways of optimizing workflows, yet there’s a learning curve to new software and many automation tools require specialized knowledge to set up and manage. The burden is still on users to unlock value, integrate with other tools, and orchestrate all the pieces.
Even our startup team at Charli uses many apps per person to get our work done, and each app has its own set of tasks that involve data entry, updating, tracking, and organizing--nevermind the endless learning curves. And, as a distributed team (which is increasingly the norm), staying organized in order to collaborate effectively is a challenge. The bright side to this, though, is that we understand the problem firsthand. We empathize deeply with our ideal users because we are them! We live and breathe the challenge, and we’re building a solution that will bring us value too.
In fact, our entire team is now using Charli to organize and manage our cloud content including documents, invoices, contracts, agreements, and other stuff. Charli even recognizes expenses and creates reports for our team to send them off to our accountants. We also have to create and manage a data room for our investors--which is no longer a headache as Charli has taken on that task.
So what’s it all mean...
Yes, the challenges of working in today’s hyper-connected digital world are vast, and for small business owners and startup founders, these challenges run deep. While it’s easy to get excited about running your own business, it’s harder to execute some days without feeling like you’re drowning in a sea of joyless stuff.
Can you relate? That’s precisely why we’ve built Charli.
Stay tuned for my next post, where I’ll explain how Charli is built to tackle these challenges and eliminate the headaches.
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What do you think? I’d like your feedback. If you’re a small business owner, what aspects of running your business get you excited, and what parts would you rather do without?