The Sole Proprietor Dilemma: Are You Really Your Own Boss?

Since there’s only one person running the business, often times, sole proprietors assume they are the boss. But is this really the case?

Several years ago my father, a sole proprietor, hired business consultants to analyze his small business.

The main feedback the consultants gave him was this: He was so busy working in his business that he devoted no time to working on his business. Many small business owners share this common problem — especially sole proprietors without employees.

Since there’s only one person running the business, often times, sole proprietors assume they are the boss. But is this really the case?


The Truth About Management

In corporate America, not many people love having a boss. However, there are perks to reporting to a boss. For starters, employees always know what they need to do and how well they are doing because it is their supervisor’s responsibility to tell them.

If you were once an employee, reminisce back to the bosses you have had throughout your career. Think about their management responsibilities that directly impacted your role. Typically they would:

  • Assign short-term and long-term tasks
  • Set goals and practical steps for achieving them
  • Examine productivity and overall work performance


The Sole Proprietor’s Management Dilemma

What happens when there is no boss — no single person managing other people, as is the case of a sole proprietor? The business entity, owned and run by one individual, has no legal (and in most cases operational) distinction between the owner and the business.

Often critical management duties are placed on the back burner because the work of running the business takes up every minute of the day. If there are customers to service or orders to ship, that work will always take priority over goal setting, productivity examinations, or planning.

Management tasks are difficult to accomplish because, for sole proprietors, they require self-analysis. It is much easier to stay busy with work than to take the time for self critique.

As a result, many sole proprietors never set goals or analyze business productivity. They wake up Monday morning, start completing busy work and putting out fires rather than allotting time for pivotal tasks that can grow and expand their businesses.


How Sole Proprietors Can Become Better Bosses

It is essential for sole proprietors to set aside time to work on their businesses, in contrast to solely working in them. Here are three simple ways to get started:

  1. Review a daily or weekly to-do list.

    If you start the day, or week, without strategic direction you will easily become busy, but not necessarily productive. To remedy this, set aside time and examine your to-do list. An ideal time for this activity is on a Sunday evening before the week starts or a Friday afternoon as the week winds down. For example, I try to do this on Sunday night before the start of each week. At this time, I’m not in a busy “get things done” mindset and I can be more objective about the week ahead. I take 10 minutes to create a to-do list, prioritizing the most important and productive things for the week that will help me reach my goals.

  2. Separate strategic and tactical tasks.

    For me, this is a physical separation on the white board where I list my tasks for the week. One side illustrates the work I am planning to do on (i.e. strategic work) my business including overall strategy, operations and goal-setting. The other side of the white board lists the tasks I am doing in (i.e. tactical work) my business. In my case, working in my business includes developing websites for clients. Depending on the nature of your business this may prove difficult. For example, if you ship orders and answer a phone in your garage, you may need to get out of that space, literally, to work on your business. An escape to a local library, coffee shop, or even another office might be all it takes to clear your head and get you in the right mindset.

  3. Have an out-of-body experience.

    Don’t worry. I’m not going get too psychological with you here, but an out-of-body experience is a good way to visualize the type of self-critique you need to manage yourself and work on your business. Examine your work from an outside vantage point, as if you were another person. Evalutate the work that was done throughout the week and ask the following questions:

  • Did I complete tasks that helped me reach the goals I’ve set for my business?
  • Did I waste time doing things that were not on my to-do list?
  • When and where (i.e. time and location) did I complete my most productive work?
  • Which tasks produced the best results; and should I repeat them?

Sole proprietors start small businesses to “become their own boss,” but it’s probably time for many to actually start managing themselves. In fact, they might just end up being the first boss they’ve ever liked!


Ryan Bowman makes his online home at WebEminence.com, where his mission is to create 200 websites for small business clients who need a simple affordable website. He also writes a blog for small business website owners.


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