Avoiding danger is no safer in the long run than outright exposure. The fearful are caught as often as the bold.
—Helen Keller

Halloween—the entire month of October in fact—has become a time of spooky, scary, and creepy excitement. Halloween is one of my favorite holidays; I love carving pumpkins, roasting the seeds, and finding the perfect costume. I delight in answering the door for all the trick-or-treaters and seeing the vast array of costumes, and I finding extra joy in handing out something tasty (meaning, not a box of raisins). One of my favorite parts of Halloween is attending music festivals and seeing everyone dancing their socks off in their best costumes. Regardless of how you celebrate Halloween this year, it will undoubtedly be different from the norm for all of us.

In honor of this monthly theme, I thought it would be fun to share some of the scariest things that I see business owners do. Hopefully, you and your business can avoid these haunting experiences and go from fright to fortune.

#1 Spook: Lack of prioritizing / self-discipline

“I wish I had more time.”
This is something I repeatedly hear from business owners. The struggle is real. When unsure of how to manage time, creating space to organize necessary tasks often fall by the wayside. This results in a twofold problem: inability to prioritize or to practice self-discipline.

This is a slippery slope to slide down when accountability falls solely on you. Because you are your own boss and calling the shots, you can take time off whenever you feel like it. When these absences are unplanned, you’ll likely have to play catch up when you return due to time management and planning failure.

Running your own business means that you only answer to yourself (and your customers/clients). One of the most incredible things about being in business for yourself is that you have complete control over all decisions: both the good and the bad. This is all great unless you don’t have a handle on managing your time. If you lack discipline, being in business for yourself can quickly feel less like freedom and more like wrangling a monster. Being overwhelmed by competing priorities, stressed about not making strides in what matters most to you, and distracted by unimportant interruptions (often self-inflicted) inevitably leaves you struggling to stay on track to meet deadlines.
Think about how are you reacting. How are you responding? How are you behaving? All of those things are within your control. Prioritizing allows you to focus on the most important tasks first—be clear about what you have to do. Create items and paths, and then milestones for those items. You are on course, and you have to reach particular milestones.
This slope gets more slippery as you get distracted by the less important/more fun tasks over the necessary ones—often feeling less and less urgency to take care of what needs to get done. You get distracted but still feel a sense of accomplishment at having done something, anything, even if the achievement isn’t valuable. Also, the more of these nonessential tasks you finish, the easier it is to push the essential ones to the periphery.

Not-so-scary solutions:

Give up some free time or flexibility? Doesn’t quite make sense. I want all owners to be agile and flexible. This is a crucial skill as an entrepreneur, but sometimes, the flex is in being more disciplined, focused. Being a dedicated business owner requires this from time to time, especially when you are starting out or during the high season of your business. You do not have to be a martyr; just work smarter!
Prioritize your tasks: Work backward from what is most important.
Commit to setting deadlines for your projects, and complete them within the time frame you set for yourself.
Avoid over-planning:
  1. Be realistic about your deadlines and goals.
  2. Overestimate the time it will take to accomplish each task, as we often underestimate our ability to get it done.
  3. Note how long a job took to become more aware of your time.
Turn off your devices/notifications.
Schedule your time off as you would if you were working for someone else.
Practice self-care: Check-in with yourself, and find ways to nurture yourself before your tank is empty.

#2 Scare: Not establishing good habits and routines

One of the best perks of being your own boss is establishing your own rules, with your working hours being one of those highlights. You can take as many breaks as you want, for as long as you want, and if you feel like blowing off the day to play, you can without anyone coming down on you (other than your own conscious). All of this is awesome until it catches up to you, and you find yourself wondering where your time went, how your projects backed up, how employee issues emerged. Suddenly, it seems, you are out of balance.
This doesn’t need to happen to you. One of the biggest pitfalls I come across is allowing this flexibility to derail you from your responsibilities to your customers, your employees, and yourself. When things get challenging, business owners tend to avoid the issue, brush it under the rug, or throw in the towel altogether. While taking a step back is good practice and allows for a fresh perspective, complete avoidance is not a good thing. Out of sight does not equal out of mind; problems do not go away, and they become an energy suck.

Not-so-scary solutions:

Get the support you need: You may have the knowledge and skills to perform your business’s necessary functions, but it may not always be the best use of your strengths or time. Finding the guidance you need to enhance your business skills with candid feedback on the progress and growth of your small business can be a priceless investment. Enlisting other professionals to help guide you with areas if weakness allows for greater effectiveness and efficiency. For example, hiring the right employees is a challenge for most businesses. Many small-business owners have little to no hiring experience, and they are unfamiliar with the differences between onboarding, training, and developing an employee. Getting help selecting, screening, and interviewing an employee is crucial. You may also need administrative support, IT professionals, or marketing specialists who can help take your company take its next steps to grow the business. Many business owners mistakenly think they can do it themselves, that they will save money and costs in the long run.
Create a schedule and stick to it: Even if you’re working from home, this will give you the structure to accomplish what matters most for your success. Setting aside time creates boundaries for everyone, including yourself.
Know when and how to “turn off”: Schedule downtime, and plan your time off.

#3 Creep: Falling behind in bookkeeping and tracking

Keeping up-to-date on business financials seems to be a challenge for almost everyone. This often stems from poor financial planning at the onset of your business. Let’s face it, having a system for bookkeeping and expenses isn’t the sexiest part of owning a business, and though it feels great to count the money that comes in, it is difficult to see what goes out. Staying on top of invoicing, records, and balancing your books saves valuable time and money down the road. These practices give you the information necessary to make smart decisions and grow your business.
Often, business owners will mix personal and business finances. Keeping these two entities completely separate makes for much easier accounting, budgeting, and reconciling the two sets of books to determine actual profits and losses. Mixing finances also means that come tax time, there will be a lot of confusion and likely many headaches.
COVID-19 has shed glaring light on many business owners’ lack of bookkeeping—paying little attention to trends and patterns until you see a dip in revenue is not an efficient way to manage your numbers. Many have dealt with penalties, having allowed interest to accrue with the IRS and the state. Being occupied with the day-to-day management of finances does not mean neglecting tax responsibilities. Paying taxes quarterly on your income will avoid surprises when tax season rolls around.

Not-so-scary solutions:

Schedule time each week to do your accounting and invoicing.
Reach out to staff to address financial strategies.
Utilize accounting software, like Quickbooks.
Know your POS system, its features, and how to reconcile and utilize its reports.
Create a clear delineation between financial boundaries, primarily to protect personal assets.
Pay yourself compensation.

Be prepared for a rainy day: Keep a safety net of two months of operating costs. COVID-19 likely depleted these funds. Force yourself to rebuild!

Hire a monthly bookkeeper/accountant: Professional assistance can help you get back to the aspects of running your business that you enjoy. Working with an expert saves time and money down the road. They can advise on operating your business in the most tax-advantageous way possible and increasing your business’s revenue potential. A monthly accountant provides a measurable impact and the results you need to stay competitive and grow. Shortcutting on professional help always catches up—take my word for it.
Establish a business entity, like an LLC or SCORP.
Pay your taxes on time.
Owning your own business doesn’t have to be scary! Avoid the everyday horrors by being mindful of your priorities, establishing good habits/routines, and keeping up on the not-so-glamorous back-end responsibility of accounting. The root of these scary things can all be boiled down to one noxious potion: avoidance. Avoidance of the obstacles mentioned above will only bring pain and a nuisance for you and your business.
By implementing these not-so-scary solutions, you can avoid the potential horror that could come to haunt you and your business. I offer the gift of perspective to lighten the burdens of these common business nemeses. Reach out to me so that we can implement change to reach your utmost success!
Arianne