In the spring of 2015, I decided to open my own brick and mortar business. I had been a massage therapist for about four years, and I was… let’s say mildly frustrated… at my professional prospects. I recognized that in order to advance my career, I needed to level up from worker to entrepreneur.

Like many workers-turned-business-owners, I knew almost nothing about how to actually run a business. Fortunately, there is a wealth of information online from those who have made that journey, and I drank up their knowledge and experiences. Over the next five and a half years, I grew my business from “I am making enough to cover my business expenses and maybe take myself out to lunch once a month” to “I am paying all of my bills with a little leftover,” which helped tremendously when the pandemic hit and I was compelled to finally close my doors.

(I’ll skip the details of my decision to close my first business. Suffice it to say, I weighed the costs of continuing to operate against the risks of starting a new venture, and now I am in a new city working from my cozy old house as a freelance blogger and writing coach.)

Over those five and a half years of running my first business, I learned some things that go beyond the practical, material concerns of being a solopreneur. In this post, I’ll share some tips and strategies to help you with what I think is the most critical:

How to actually be a good boss for yourself

One of the primary benefits of not starting a business, of continuing to work for other people (whether as an employee or a contractor) is that you don’t have to do the hard work of managing yourself. As many folks discovered in the early days of the Covid-19 lockdown, managing your work environment and tasks without someone looking over your shoulder can be daunting.

When you’re your own boss, you have to make all the decisions and set all the boundaries for yourself and your work. It’s easy to get overwhelmed. Critical things fall through the cracks, which stunts your fledgling business’s growth (and your income).

It’s so easy to fall into the mindset of forcing yourself to do too much all at once.

It’s easy to establish unhealthy patterns that you wouldn’t tolerate from any boss you’d work for as an employee or contractor.

So let’s address some of these problems with solutions I’ve found for each of them over the years.

Tip #1: Be a good boss by setting and respecting your boundaries

Being able to set your own hours has a lot of benefits, but it also has a lot of downsides too.

When you’re self-employed, it’s entirely too easy to “take your work home with you.” This is especially true if, like me, your office is literally in your home. Without clear boundaries, you will begin to sacrifice not just leisure time with family and friends (or just yourself), but important self-care things like exercise, healthy eating, and even sleep.

And when your clients and customers reach out to you at all hours of the day and night, it’s difficult to resist the temptation to respond immediately. After all, if you don’t respond right now, they may take their business elsewhere, right?

The primary issue with weak boundaries is, to put it bluntly, a lack of respect for your own time and well-being.

We all intuitively know that “you can’t pour from an empty cup.” But setting those boundaries can feel scary, even overwhelming.

If you’re in the position I was early in my self-employed journey and have no boundaries set up, here’s what you can do:

1. Set clear work hours and stick to them. If your office hours are from 9AM-5PM with a one-hour lunch break at 12PM, respect those hours. Don’t be a bad boss and demand that you work outside of your regular business hours. Once you clock out for the day, you need to be done. No exceptions.
2. Well, almost no exceptions. But make the exceptions truly exceptions. If a client wants you to work outside of your regular business hours, you should almost always respectfully decline (“I am not available at that time, but I am available at X time if that works for you”). If you decide to accept work outside of your regular hours, communicate clearly to your client that this is a one-time exception, or charge them significantly extra for the trouble.
3. Only check your email and messages during your regular business hours. If you only have a single phone for both work and personal use, do not allow notifications from your work accounts when you are not actually working. Most email clients have auto-responders that you can set up to reply to any emails you get outside of your regular hours.
4. Resist the urge to continue engaging with work when you are no longer working. This can take time and practice. (I began using sticky notes and eventually a bullet journal so I could make notes of the work-related things I was compelled to do outside of work hours. That way, I was able to incorporate those things into my work schedule over the following few days.)

If you find that your boundaries are weak, consider asking yourself whether you would allow a boss at a “regular job” to make these sorts of demands from you.

Setting and navigating your own boundaries can take some trial and error, especially if your clients and customers are used to you being available all the time. I promise that it’s worth it in the long run, though. Your customers will respect you more when they know your time is precious, and you will have a more pleasant relationship with your business.

Tip #2: Be a good boss by outsourcing your areas of weakness

When you are self-employed, you quickly find yourself wearing too many hats. You have to do literally everything in your business. This can quickly become overwhelming and lead to burnout.

If you had a boss that piled on responsibilities that you weren’t qualified to do, responsibilities that took time away from your actual areas of expertise, you can bet you’d develop some resentment and start looking for the door.

But what can you do?

Well, the answer is simple, even if it isn’t easy:

Take an inventory of those tasks that you struggle with, and outsource them to other qualified professionals.

I know, this is a huge ask when you’re first starting out and you may not have much overhead to work with, but please trust me on this one.

Like many things in running your own business, recognizing your limits and hiring people to help is an investment. When you compare the cost of doing these things yourself (which takes time and energy away from the parts of your business that utilize your strengths and bring you joy) to the cost of hiring someone whose expertise is doing those things, you will often come out ahead.

When you’re looking to outsource work, this could mean:

• a virtual assistant to help you with answering emails, scheduling, and keeping appointments
• a phone answering service to field calls from customers and suppliers
• an accountant to help you with your budget and taxes
• a freelance writer to write your blog posts, website copy, email newsletters, and sales copy (like yours truly!)
• a graphic designer to make beautiful posts for your social media accounts
• a custodial service to clean your place of business

By delegating the business tasks you don’t enjoy, you have more opportunity to grow your business and increase your income.

Which brings me to the third strategy to being a good boss for yourself:

Tip #3: Be a good boss by recognizing and rewarding your strengths

Once you outsource the work that clutters up your workday, you’ll be left with the work that lights you up – or at the very least doesn’t drain you.

You may be tempted to leave it at that, and simply carry on with your work routine. But there are a few strategies regarding your strengths that you can implement to increase your work satisfaction as a small business owner.

We’re talking about being a good boss to yourself here.

So when you’re doing the work that you do well, treat yourself like a valued member of your corporate team, rather than taking your own presence for granted.

When you’re doing the work, when you finish a project, when you complete a task, take some time to recognize your efforts.

Reward yourself for a job well done.

This may be as simple as making a note to yourself about how well you handled a particular project or customer, or as involved as taking yourself out for coffee or lunch.

The key is to establish and reinforce positive behavior in your mind. Obviously, you’ll want to save the more extravagant rewards for those times where you went above and beyond.

And you’ll want to make sure to truly unplug from work when you’re enjoying those bigger rewards (don’t check work messages when you’re having that celebratory pastry!) to reinforce in your psyche that your hard work and talents are appreciated.

Speaking of taking yourself out to lunch…

Tip #4: Be a good boss by having “company meetings” with yourself.

If you’ve never tried this particular strategy, it can sound really hokey, but I promise you’ll see a big increase in your own morale and productivity when you implement it.

When you’re a one-person show, regardless of how many other professionals you’ve hired to help you, you still carry the weight of making and implementing all the plans to make your business run smoothly and grow.

There are so many moving parts to a business. When you’re in the weeds, it can be difficult to maintain the perspective needed to help your company thrive.

Enter: The CEO Date.

At least once a month, physically leave your usual workspace (work strategy meetings don’t usually happen in a cubicle, after all) and have a meeting with yourself. Go over everything that’s happening in your business, and the plans you have going forward to fix problems and help the company grow.

Take the time to strategize and make plans to address issues in your company. This will help you feel more in control of your situation (which is surprisingly difficult when you’re self-employed) and reduce your anxieties about problems and unknowns.

And now, on to the final, and perhaps most crucial tip to help you be a good boss for yourself:

Tip #5: Be a good boss by cutting yourself some slack

“Listen. Mistakes happen. Don’t beat yourself up about it. Let’s just fix it, learn from it, and do better next time.”

When you run your own business, you will make mistakes.

Most of the time, these mistakes will not be catastrophic. If they are, that is definitely a time to see what went wrong and seek outside help to fix the problem and prevent it from happening in the future. (The same goes for making the same small mistake over and over again.)

Occasional small mistakes, though? Those are valuable opportunities to establish a healthy work environment not just for yourself, but for future contractors and employees who will take over those responsibilities as your business grows.

A small mistake is not the end of the world or your business.

In fact, mistakes and failures are some of the most powerful tools to improve your company.

Mistakes are opportunities to tighten your systems and operations and make compassionate human connections with those who are impacted by the mistake (whether that’s only you, or also a customer, employee or contractor, or supplier).

When you realize that you have made a mistake in your business, seize the opportunity to establish a healthy work culture. Treat yourself the way you would want a boss to treat you.

Don’t let yourself off the hook, but don’t bully yourself about it.

Solve the problem, examine why the mistake occurred in the first place, and then set up a system to help prevent the same sort of mistake from happening again.

Conclusion

By using these five strategies, you will start to see a change in your attitude toward your work. You will have more power in your business (“work on your business, not just in your business”) and a healthier relationship with your work.

Plus, as your company grows and you need to add people to your team, you will already have established a workplace culture that helps everyone feel more safe and supported. Everyone will be able to do the work they are skilled at without the expectation of constantly picking up work they aren’t good at and loathe. Your team will be more motivated to strive for excellence, and they will be able to address problems as they arise (and even beforehand).

By being a good boss to yourself, you set the pattern of being a good boss to others. This helps make your company a better place to work and do business with. Customers can feel the difference as well, and they are more likely to respect you and your company because of the high standard of humanity you set for your company’s culture.

Now go forth and be a better boss for yourself!

Footnote: this blog post is an example of a long-form educational “how-to” style blog post. If you would like me to write for your blog, check out my current rates for individual posts, or send me a message using the form below to inquire about a longer-term arrangement. I look forward to hearing from you!

~Bea