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Making Entrepreneurship Work for You

Behind The Scenes
I’m often convinced that self-employment is simply one never-ending learning experience. So much of what it takes to succeed is simply learned over time in the act of doing, and I continue to learn new lessons with each project we tackle. For example, I’ve worked on several projects—as I’m sure you have as well—where an unexpected hiccup arises midway through the project, throws the timeline off course, and forces me to find a solution. Challenging as it may be at the time, handling situations like these help me make better and more informed decisions down the road. Even if the specific hiccup never arises again, other things inevitably will, and I’ll be better equipped to handle them when they come around.
Author Jessica Comingore

Bring this same approach into your own business to build a thriving, stable foundation for long-term success. Rather than trying to learn everything—and get everything right on your first try—focus on taking your business seriously, and equipping yourself to handle and learn from your mistakes. It was only once I accepted the reality that there will be mistakes, and there will be screw ups in my business—no matter how hard I try to learn them before experiencing them—that I was able to grow as a business owner, and step into being the leader my business needed me to be.

Over the past several years in my own entrepreneurial journey, a few things stand out as being the most beneficial for long-term balance and success:


Flexibility is often named as a benefit of self-employment, but it can be incredibly easy to get carried away with that, and allow it to impact your overall mindset. You still need to run a serious business, which means creating accountability and structure for yourself. If you’re prioritizing errands, friend lunches, and naps consistently over the needs of your business in the name of “flexibility”, your business will likely struggle to grow. The more seriously you take yourself, the more seriously the business runs, and flourishes like a business should.

For example, when it comes to structuring time and days, I tend to keep a standard 9-5 schedule (at least Monday through Thursday). As much as I wish my set-up was more flexible at times, at the end of the day, this is my full-time job, so standard office hours are when I’m devoted to work like business growth, client communication, and project management. Even if it isn’t a conventional 9-5,consider what working hours are best for you, set them, and stick to it. It may be hard at first to turn down a pool afternoon the first time your friend calls, but the impact you’ll see this discipline have in your business will be worth it, I can promise.

Time tracking

In addition to your business being serious, it also needs to be profitable, which means pricing your work correctly. To do that requires an understanding of your own processes, and how long it takes you to complete a variety of tasks—especially when you’re just starting out. If you aren’t paying close attention to your hours, it makes it almost impossible to price projects appropriately.

To ensure maximum profitability with each of my projects, I still track all of my tasks in Toggl each day to see how long they take. This way, I’m able to easily tag tasks throughout a project, and look back on them when it comes time to price a project with a similar scope in the future. The amount of time involved, the tasks included, and which team members I need to enlist are all laid out clearly. It also helps me better judge issues that could arise from those occasional time consuming and unexpected hiccups in the middle of a project that I mentioned earlier.

Managing projects, people, and income is critical at every stage of business, and doing so helps me ensure that I’m estimating prices that not only cover my costs, but also ideally turn a profit.

Financial system

Finally, it’s important to have tight systems in place for managing your business’s money when it does come through the door. As an example, I divvy up my own income by putting 10% toward taxes, 10% to long-term savings, and 10% to emergency savings.

Truth be told, when I first ventured into the world of self-employment, it was a somewhat premature leap. I didn’t have a savings in place, and used credit to get things off the ground, only leaving me to dig myself out of debt later. This system has been a game changer for my business’s cash flow, and I follow this formula with every check that comes in, even if it’s $100.

Savings and financial security accumulate quickly when you have a plan for your finances from the start, and pay attention not to spend beyond your means. Again, it will be hard to turn down that spontaneous spa day if it doesn’t fit within your budget,but when your budget is paired with getting paid what you’re worth, it can finally stabilize your business’s cash flow, and allow you to invest in resources that will be necessary for growth in the future.

Once you begin implementing these boundaries within your business—even if you just start with one and work your way up to implementing all three in time—you’ll notice profound effects on your mental health, the health of your business, and start to see the early signs of sustainable growth take hold. Personally, I’ve found that the more structure and boundaries you set for yourself within your business, the more your business will thrive. It seems counter-intuitive, but it’s true.

How did the idea of flexibility sabotage your business when you were first starting out? Was it like a kid in a candy store or did you bring the 9-5 structure immediately over into being your own boss? What structure do you have in place in your business now to take it more seriously? Share your most successful tricks with us in the comments below.

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One thought on “Making Entrepreneurship Work for You

  1. I’ve been making an effort to apply the lessons of each project/client to the next as I try to figure out best practices as well. Looking to improve systems whenever I can and I so appreciate you sharing your insights! xo

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