How to Rate Yourself as an Employee When You’re the Boss?

There’s no reason you always have to go it alone, just because you’re a solopreneur or freelancer. Being your own boss can be as tough as it is rewarding, especially once you realize you are also your own employee. There’s no shame in not wanting to be ‘Chief Cook AND Bottle Washer’, especially if you really hate washing bottles, and went into business for yourself because you love to cook.

The good news is, finding the right help is easier and more cost effective than ever thanks to the Internet, and can save you time, money and stress. Here are five questions to ask yourself to find out if you need outside help:

1. Do I want to be my own employee all the time?

What if you had to write your own performance review? How would you rate yourself as an employee?

If you’re anything like me (and every other solopreneur or freelancer out there), you went into business for yourself because you wanted to be your own boss. Perhaps you wanted a flexible schedule, or the freedom to pursue the types projects you enjoy working on, and the types of clients you like working with? Maybe you just wanted to be able to set your own salary goals, and be responsible only to yourself to meet them? Whatever your personal reasons for going it alone, you should still take the time periodically to ask yourself if you also wanted to be your own employee all the time, and how you’re doing at your job?

Even if you were a rockstar as an employee in the full-time world, being the boss of you can be tough. It’s one thing to answer to clients, and deliver the work they ask of you. Presumably you are good at that, or you wouldn’t have considered starting your own business doing that work in the first place.  But what about the work you need to ask of yourself? If you were your own client, responsible for delivering work in support of your own business, how would you rate yourself? If you’d give yourself anything less than a rockstar rating, guess what? It might be time to find your own replacement by seeking outside help.

2. What kind of help do I really need?

This is one of the best questions you can ask yourself before seeking outside help. There are really three steps to answering this question:

Step 1: Make a list of the non-billable things you are doing, and how long it takes

Figure out how much time per day or week you are spending on non-billable work. Is it work only you can do, or could it be outsourced to someone else? Literally sit down one day (or across an entire week) and document what you’re doing in writing, how long it took, what systems you used, etc… Keep track of every minute, not just the time you spend on each task, but even transitioning between tasks. Did you know it can take you 20 minutes to refocus on work after checking email alone?

If you are losing momentum, it will show in list.

Step 2: Make a list of the non-billable things you aren’t doing, and why

Figure out which tasks you know you need to do, but aren’t doing at all. Unlike step one, in which you documented the things you are doing on your own, that perhaps someone else could do for you, this step will probably involve you sitting down and going through your past to-do lists, and looking at all the things you’ve never crossed off, that keep getting put off or moved forward in time to some future date that never seems to arrive. These might be things like “Update my blog,” or “Brainstorm marketing ideas,” or “Research project management software.

Everyone has these items on their to-do list (yes, I have them too). Find yours, and see if there’s a pattern. Do they all revolve around things you aren’t good at, activities you don’t enjoy, or require the use of tools you don’t even have? See what they have in common, and write that down too.

Step 3: Figure out what kind of delegator you are

Let’s face it, some people (many of them freelancers and solopreneurs in fact) are uncomfortable delegating. The very independence and entrepreneurial spirit (not to mention work ethic) it takes to go into business for yourself can make it that much harder to both admit you need help, and to get effective help because these traits can make it harder to let go and trust others to meet your high standards.

Others are perfectly comfortable with letting go, especially of tasks that bog them down or they hate doing, but they went into business for themselves because they didn’t want to be a boss, weren’t interested in managing other people, or having other people needing their input or feedback on a regular basis. For these folks, the thought of getting outside help might seem like a way to create different work (managerial tasks perhaps), rather than a way to offload work.

Still others are only comfortable letting go for defined periods of time, on a project basis perhaps. They know they need a new website or content strategy, or perhaps a new CRM system, but they need someone else to design and built it, analyze and recommend it, or research and implement it, leaving them to self-serve after that.

Most people are a combination of these types, and often it depends upon the tasks or the business you’re in, but it’s very important for you to figure out which one you are in relation to the things you identified in steps 1 and 2 if you’re going to find the right kind of help, never mind the right person or people to provide it.

Take your first two lists, and make a note of your comfort level delegating the tasks you identified. Which ones would be projects, which daily or weekly activities? As precisely as you can, assign a time-budget and deadlines for each. This will help you answer the next couple of questions.

3. Am I charging enough for my services?

Let’s say you answer question 2, and realize you’ve reached that point where you are looking for help–for someone else to do those things you don’t like doing, or that keep you from doing the things you went into business to do in the first place. What that means is, you’ve also reached the point where it’s time to look at your rates.

If you are so busy with client work you can’t find the time to do business development, marketing, and client service, or conversely, are so busy doing those things you can’t do your best work for the clients you have, chances are you are in-demand enough to raise your rates commensurate with what it will cost to get the help you need.

Take a look at the time-budgets for the tasks you identified, and do the math. Pretend it’s billable hours for the things you are doing, and pretend it’s unrealized gains for the tasks you’re not doing at all. I realize it’s hard to quantify the money you might be ‘losing’ because you haven’t done something, but common sense alone will tell you there’s a reason you put those items on your to-do list in the first place, and there’s a cost associated with never getting around to them. Even if you’re swamped with work right now, if the things you push to the back burner are marketing and prospecting tasks, you could end up with longer dry spells simply because you didn’t establish a plan for keeping your pipeline full.

4. What’s the ROI of hiring help?

Consider this: Every hour you spend doing work clients don’t pay you to do is an hour’s worth of your time, at the rate you charge, spent. You can look at it as an ‘investment,’ or you could look at it as what it is: money out of your pocket.

Let’s say you charge your clients $100/hour. If you spend 2 hours per week doing admin. or business development work, that’s $200 you just ‘invested’.

What does the ROI need to be on $100/hour vs. $25, or $50/hour you might pay someone else to do the same things?

ROI aside, what if you could get someone else to do that work for you for half as much? That’s $100 you just saved.

4. But how does hiring help impact my cash-flow?

Good question! What about it? Where does cash come from when you’re in business for yourself? The money your clients pay you, right? Well what if you have to stop producing billable work to do the work to collect it? What then? That hour you spent producing and sending invoices, and the other hour you spent making reminder calls to clients? There’s 2 hours gone–or $200 invested in getting your hands on the cash you’re owed.

Let’s look at that marketing example again. How will it affect your cashflow if you don’t put time into non-billable tasks like promoting your business? What if you end up in a long dry spell without work? Even if you have several regular, loyal clients or customers, their budgets might suddenly be limited because they didn’t plan ahead either. Maybe they will find a way to automate, or your project for them will wrap up? Anything can happen. If you are dependent on a few clients, all it takes is for one to scale back, or move on to hurt your cash flow.

If you’re busy enough now that you don’t have time to do everything you need to do yourself, an ‘investment’ in outside help could end up protecting your future cash flow too.

Expenses and budgets are what they are, but it’s worth taking a look at yours honestly, and asking yourself how much time (read: money) you are already spending by not having someone to help you with your non-billable tasks.

5. What can I spend paying other people to replace me?

If you’ve answered the questions above following the steps as-written, you should have a pretty good idea what you are ‘spending’ right now doing (or not doing) work for yourself. You are paying yourself that much already. Your task is to decide how much of that you would rather pay someone else instead.

Then ask yourself what type of person you realistically expect to get for that amount? There are many resources online where you can find other freelancers and Virtual Assistants to meet the needs of a wide variety of budgets, but as with everything, you often get what you pay for.

oDesk, Elance, and Freelancer are great resources for Virtual Assistants, especially if your budget is very small. You can find people who will work for you for as little as $3/hour because they are located outside the US, or are doing work on the side, as a part-time thing to make a little extra money. You can also find specialists in a particular field or skill set, if you know precisely what you need, for how long, and how much you’re willing to pay. These services do require you to spend time posting a request for a proposal, and then reading through what could be dozens of responses in order to find the right person, but you may find their typically lower rates, or the ability to read feedback from other clients worth the time on your end.

If you have a regular need, for someone on retainer, who is perhaps answerable to a boss of their own, you might consider trying a business concierge service like Red Butler. Red Butler works very differently. You purchase a plan that gets you a certain number of requests per month. The more dedicated your help, and the more requests you want to make,  the more you will pay. This is great for those with a higher monthly budget, who need dedicated support and the ability to make short-notice requests to someone “on-call” as well as on retainer.

For more great tips to help you figure out if you’re charging enough, or if hiring outside help or a Virtual Assistant would be better use of time and money than doing it all yourself, consider reading any or all of the following:

7 Reasons You Should Hire a Virtual Assistant, by Michael Hyatt

Startup Bros-The Virtual Assistant, by John Gower

Should You Hire a Virtual Assistant? by Andrea Ayers

Answer these 5 questions for yourself, then get in touch to set up your FREE 30 minute consultation to talk about how I can help you make the most of your time!


  1. Great article! Too many entrepreneurs and solopreneurs (myself) included spend time on non-billable items that should be delegated. This article should be an eye-opener to any small business owner who wants to grow their business.

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