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How to Play Both Sides: Having Two Different Careers at the Same Time

Within today’s economy, it’s not uncommon for people to pursue two careers. According to the U.S. Department of Labor, approximately seven million Americans work multiple jobs. For some, their choices are strictly based on financial gain while others take on a second career in order to pursue a less lucrative passion. Either way, working two careers can be fairly complex.

See Also: How to Handle Multiple Jobs 

In order to be successful in playing both sides, you will need to possess excellent time management skills. As you experience more within your career choices, they will open up more professional opportunities. In many cases, roles within one career will benefit roles within the other, through newly learned skills, networking, or simply by taking a break from routine. If you are currently working within two careers or plan on taking on a second career in the near future, it’s important to understand balance. When you effectively play both sides, you won’t allow one career to negatively affect the other. In fact, if you’re strategic in terms of your approach, you can actually benefit each career based on the other. Here are some simple tips to remember so that you continually reach your professional goals without increasing your risk of failure or burnout.


1. Set Boundaries

In a perfect world, everyone who has two careers would have overlapping tasks that benefited their other career. Unfortunately, the reality is that that is highly unlikely, many individuals who work two careers find that their two jobs are a hundred percent independent of one another. Regardless of your roles, your boss will more than likely want all of your time. Since you have two bosses to please, you’ll need to set some boundaries. If you let both bosses dictate your schedule, you’ll end up burning out in a flash and you won’t be able to perform as well as you’d like to in neither job.

Whenever possible, decide what you availability will be for one career. Based on that availability, you can shape your hours for your second career. For example, you may work an office job, working an average 9-5 shift, Monday-Friday. Perhaps your second career is your own personal business. The time you put in for this career will need to be in the mornings, evenings, and on weekends.

Once you decide on your working schedule, ensure that you give yourself one day a week where you’re not working within either career. You need time to unwind and tend to your personal needs as well. Put your foot down if you’re being asked to work hour outside of your original agreement. It’s critical that you learn to say no.

2. Choose Variety

When it comes to your careers, choosing variety can be really helpful. For example, think about a customer service position. If you’re working two careers within this field, you could potentially work 60 hours, dealing with headache-causing complaints and grumpy people. Instead of taking on a second career doing the same thing as your primary job, opt for something that will give you a break from your primary roles. 

You’ll also need to focus on the level of physical activity that’s required of you from both careers. If your first job requires you to sit at a desk, then your second job could really benefit your health if you opt for something that’s more physically demanding. It’s important to analyze how each career will not only affect your schedule but your mental and physical health as well. If you’re overly fatigued, this will amplify poor lifestyle choices, ultimately affecting your overall well-being.

3. Accept Some Levels of Chaos

Although you may want to simply work 40 hours a week and spend the remainder of your time relaxing, this isn’t an option for everyone. If you are already involved in two careers, you know that life gets hectic. One career is stressful enough so once you throw a second career into the mix, things can get a little crazy.

It’s important to accept the fact that some days will be a little hectic. With that being said, just because you have a lot on your plate, doesn’t mean you need to lose control. Accepting this can bring you a peace of mind and help keep you grounded. If you have been working multiple jobs for years and are still only scraping by, you should start looking for other opportunities or negotiating a raise. Understanding that some level of chaos is inevitable is important, however, recognizing when your efforts aren’t worth the rewards is just as critical.

4. Set Goals

Before you take on a second career, it’s important to focus on your short and long-term goals. Why is it that you’re taking on a second career? If your goal is financially based, ensure that you’re putting all your extra money towards your debt, buying a home, or any other financial goal you’re working towards. This will ensure that your hard work is worth the extra effort.

If you are taking on a second career to pursue a passion of yours, have clear goals in mind which will allow you to advance. Ideally, you will only have two careers for a short period of time. You will need your original career in order to fund your new budding career. Make sure you continually assess your goals and take the right course of action, ensuring that you’ll reach your end goal. If you work towards your dream job and succeed, you can then focus on that one career full-time without needing your second career.

5. Don't Talk About Job A at Job B

To be fair, not many bosses will be crazy about you having a second career. Why? Well, they’ll think that you’re spreading your efforts thin. This is why when you’re at one job, your focus needs to be entirely on your duties within that position. You cannot work on assignments from job A while you’re at job B. When one company is paying you, you’ll need to ensure that you’re a hundred percent focused on the tasks that need to be completed within that company.

It can be tough to know whether or not a manager would react poorly to you having a second job. Although they may know you have a second career, don’t discuss details while you’re working. As far as their concerned, you work for them and while you’re at work your focus should be on what’s required of you. Although there are some special circumstances when your employer can step in, such as a non-compete agreement, there’s nothing wrong with having two careers. The key is to understand that you should keep both careers separate.

 See Also: Maintaining a Healthy Work-Life Balance 

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The sad reality is, many individuals will need to work within two careers in order to sustain a basic standard of living. Although a second career can be rewarding, make sure you’re able to handle multiple jobs. If your time management skills are poor, work on these before taking on your second career.

Continually assess your goals, allowing yourself to improve and maintain a higher standard of living. Once you have reached your primary goal, know when it’s time to quit. If you have reached your financial goal or you’re noticing that your health is diminishing, you need to lessen your workload.