5 Strategies to Survive the First Year of Your Second Job


Today’s workforce is rapidly evolving. Many professionals are opting for a side hustle in addition to their regular professional 9 to 5 job. There are a lot of reasons like a financial crisis, family priorities, experimenting different career options, and many others to take up a second job on a part-time/remote basis.

Whatever the reason is, working a part-time job along with a professional 9 to 5 job and being successful at it can pose a lot of challenges. Before taking up a second job you should do a thorough self-assessment of your strengths, weaknesses and personality to determine if it’s the right choice for you. This a critical step in determining your success in pulling off a second job, so ensure that you’ve done your homework..

So, you’ve decided to plunge into a part-time/remote second job. What next?

Once you start with your second job, the first year will be rigorous and full of surprises. You will be trying out new things, which naturally brings up lots of twists and turn. But, with proper planning and understanding of the obstacles and pitfalls and the ways to overcome them, you can turn your first year of the second job into a rewarding one. Here are 5 strategies to make your part-time / remote second job a smooth one and go from survive to thrive in the first year.

1.Pick your jobs wisely

The first and foremost step is to settle into a niche that lets you utilize your skill set. Choosing your area of expertise requires some time, trial and repetition. There is a wide range of fields and opportunities for would-be part-timers. Making money while at the same time pursuing your passion is one of the best things that can help you survive the first year of working part-time. Leverage your strengths and look out for second jobs in what you are already familiar with.

“Choose a job you love, and you will never have to work a day in your life.” – Confucius

2.Be organized

Whether you work in a regular office for your part-time job or work from home, you need to be organized to survive it. Being organized is important to maintain your balance and be able to do the jobs well. Write down your weekly plans, your daily to-do’s, create a goal for yourself and set a deadline for each job. If you’re not organized, it can create a lot of confusion and wasting precious time, which you can’t afford especially when working a second job.

“For every minute spent organizing, an hour is earned.” – Benjamin Franklin

There are several methodologies that can help you be organized and improve your productivity – Getting Things Done (GTD), Inbox Zero, Bullet Journal, One Page Project manager, Don’t Break the Chain – the list is endless. And the plethora of software and apps available today makes it super simple to implement these methodologies and stay updated with your work on the go.

3.Create a schedule & Stick to it

The schedule you make decides your long-term success. Flexibility is an important benefit of part-time work. But, it does not mean that you take a casual approach to part-time work. In the first year of your second job, it is better if you follow a rigid approach instead of a flexible one. Do not take more jobs at the same time and do not commit to work you cannot complete. Be clear-sighted with how much you time you have, take up work accordingly and schedule it.

Once you create your schedule, stick to it until it becomes your routine, and success will follow. And don’t forget the productivity techniques and tools mentioned earlier. Pretty much all of those tools have a daily calendar to help you with your scheduling, take advantage of it.

“A schedule defends from chaos and whim. It is a net for catching days.” – Annie Dillard

4.Keep up your commitment

Juggling between a regular 9 to 5 job and a part-time second job requires a higher amount of dedication, discipline and patience. The single most important thing is to keep up with your commitment. If you say ‘yes’ to a job, you should persist with it. Learn to prioritize things and find out what you may want to slash in order to finish your work. If you find that you could not complete a work on time or you’re often late to your work, kindly step back.

“Commitment is what transforms a promise into reality. It is the words which speak boldly of your intentions and the action that speak louder than words” – Shearson Lehman

Yes, you will have to make some tough decisions and that’s part of what you have signed up for. Prioritizing is an important skill that you should master if you want to keep up your commitments. Again,  there are tools and techniques to master prioritizing – The One Thing, Eisenhower Matrix, Warren Buffet’s “Not to do list” (25/5 rules) and more. Give them a read and get back to work. Concentrate on excelling in a limited number of activities. This is what will help you move further in your career.

5.Keep an eye on your Health

Burning the candle at both ends impacts your performance at either your full-time or part-time job as well as your personal life. Scientific research says that resting is actually good for your health and can also help you to be more productive in the workplace. Watch out for signs of work-related stress and anxiety, give yourself a break, have some “me time” and that should help you keep things under control. If at any time you feel that working multiple jobs is causing serious health issues, it’s time to cut back.

Taking a part-time/remote second job is all about expecting the unexpected. You might face a bit of struggle to being with, however that doesn’t mean that you’re a failure. It just means that you need to refine your ways and learn from every opportunity. The five strategies we’ve given here are the ones from the distilled knowledge of highly successful and experienced professionals. The first year of working a second job along with your regular professional 9 to 5 job is the toughest, but once you survive it, you will become a thriving professional. Best of luck to you!!!


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