Working For Yourself Vs. Working For The Man On 'How To Money'


On this episode of How To Money, Matt and Joel talk about the pros and cons of being an entrepreneur and starting your own business, or working a more traditional, 9-to-5 job. Entrepreneurship can be put on a pedestal sometimes, but there are solid reasons to strike out on your own. However, a traditional corporate job structure might be more suited to your personal goals and skills. So they get into a lot of things to take into account before starting your own business. Firstly, consider your age: The average age of a first-time entrepreneur is 39 and 42, and the entrepreneurs that fail most often are in their 20s. Starting younger has its benefits: Less to lose, less people counting on you to pay the bills, and more chances to try again in the future. On the other hand, starting a little later means you can gain valuable skills and knowledge in a corporate setting that will translate well to successfully managing your own business. And you’ll have more time to save some significant capital, so as the business is getting up and running, you can still cover your expenses.

Another thing to consider is your own temperament and work goals. If you’re working for yourself, that means you’re the boss. That’s great if you’re feeling stifled at your current job, unable to use your creative energies or pursue interesting projects or ideas. But it also means you have to set your own workload each day, and manage all the other aspects of business that might not be very interesting. For example, you might bake great cookies, but that doesn’t mean you should start your own bakery. You might be happier concentrating on the baking at someone else’s company, while they handle the insurance, payroll, sales and marketing, client services, and other administrative tasks you’d rather not deal with. Working for someone else allows you to specialize in a skill more easily, where entrepreneurs have to learn multiple skills to operate successfully.

Additionally, work/life balance can be difficult to achieve when you work for yourself. Entrepreneurship is a “kill what you eat” kind of scenario, which can mean feast or famine. When that’s the case, it can be nearly impossible to “clock out.” With a traditional job, your nights and weekends belong to you (with exceptions, of course), and there are paid vacations as well; entrepreneurs might work holidays just to keep up. However, dealing with bureaucracy and busywork, making you feel stuck or uninspired in their current career, is the number one reason most people decide to strike out on their own. The flexibility and autonomy that comes with entrepreneurship can be extremely tempting. There’s a lot to take into account before you choose to start your own business; listen to the episode for all the factors to keep in mind, and some practical steps to tackle them, on How To Money.

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