Stressors That Take the Joy out of Running a Small Business

When the novelty of being your own boss wears off, many small business owners finds themselves stressed out.

Maybe it’s a late-paying client or the realization that there’s no employer withholding money for taxes that pushes them over the edge. Whatever the frustration, the solution often involves being more organized and intentional with your small business.

Here’s a look at several stressors that many small business owners face, along with solutions.

Whatever your line of business, erratic income can throw you for a loop. After all, your living expenses may be consistent from month to month even if your income isn’t.

1. Experiencing Feast or Famine Cycles of Cash Flow

Any kind of project-based work ebbs and flows. You may have several big projects one month, followed by a leaner month once those projects wrap up. Or perhaps demand for your services is seasonal: for instance, if you run a landscaping or wedding planning business.

Whatever your line of business, erratic income can throw you for a loop. After all, your living expenses may be consistent from month to month even if your income isn’t.

The fix: One way to smooth out cash flow is to set up one or more “anchor” clients on a monthly retainer instead of just working on an as-needed basis. This is likely a client who’s a good fit for you and wants an ongoing relationship.

The benefit to you is steadier income, and the benefit to them is better budget forecasting and the assurance that you’ve reserved a set number of hours for them each month. Once you have a retainer client, you can set up recurring invoices to streamline invoicing, saving yourself some administrative time too.

2. Getting Paid on Time

Getting paid weeks or months after you complete a project is no picnic, but it’s a reality for many small business owners.

Even once 30, 60 or even 90 days passes, they’re sometimes still waiting for a check due to unclear processes or lost invoices. Late payments not only frustrate us but can create cash crunches.

The fix: Use invoicing software that makes it easy to make and track professional-looking invoices with a clear set of invoice terms and be sure to invoice promptly. Automate reminders to avoid those awkward conversations. You can even consider charging late fees.

3. Juggling Multiple Projects

Most small business owners who provide a service have multiple projects or clients running concurrently, so remembering the details and due dates for each project is no easy task.

But dropping the ball on a white paper or website project isn’t going to endear you to your clients. If you’re collaborating with other freelancers or using subcontractors, project management is likely to get even more complicated.

The fix: The right project management tools help you stay on top of project due dates, share images and files with others and more. With FreshBooks, you can even roll tracked time into your invoices, eliminating that pesky reconciliation between invoicing and time-tracking software.

So, why rely on a patchwork of Post-It notes, whiteboards or spreadsheet when you can manage projects from a single dashboard? It also creates a more professional impression for those you’re collaborating with.

4. Structuring Your Day Outside of an Office

Managing your time isn’t easy when there’s no boss looking over your shoulder or coworkers reminding you about an upcoming deadline.

Without this external accountability and the structure of an office environment, some small business owners find it difficult to prioritize and stay productive throughout the day.

The fix: Whether you bill for hourly work or not, tracking your time provides accountability for yourself and helps you gauge your productivity.

Also, if you bill clients by the hour, a time-tracking tool also provides an accurate time log for your clients and their invoices.

5. Tracking Income and Expenses

Many small business owners just want to focus on doing their work and serving their clients.

It may be a lot less exciting to keep detailed records on of the work you’ve performed, or the expenses you’ve incurred along the way.

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But a lack of organization can create huge headaches come tax time, as you scramble to find invoices or receipts. The other problem with haphazard accounting is that you may not realize that your expenses are out of whack, or that you’re about to hit a slower period in your business.

The fix: Keeping organized records throughout the year is a lot easier than gathering it all during tax season.

Using a tool that integrates invoices and expenses helps you create straightforward business reports. You can even scan expense receipts on your phone so you’ll never worry have to worry about misplacing a receipt.

Plus, tracking your profit and expenses over time helps you assess how your business is doing, which will give you a better sense of control as you grow your business and help inform smarter business decisions.

about the author

Freelance Contributor Freelance journalist Susan Johnston Taylor covers entrepreneurship, small business, and lifestyle for publications including The Boston Globe, The Wall Street Journal, Entrepreneur, and Follow her on Twitter.