Three pros and cons of the self-employed lifestyle

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Working outside: a perk of freelancing (image by Christin Hume via Unsplash)

I made the switch to self-employment two years ago, and have since enjoyed my professional life so much more. However, like with everything in life, self-employment also has its drawbacks. Here are a few ways — good and bad — in which self-employment has affected my day-to-day life.

Pro: You choose when you want to work

One of my favorite benefits of self-employment is that my work schedule is no longer dictated by someone else. I’m able to plan my work life around my personal life, whereas most people do the opposite.

A prime example of this advantage is my access to off-peak benefits. The gym, post office, and grocery store are all noticeably emptier during the day, so I don’t spend time waiting in long lines! I am generally able to travel during off-peak days and times, which saves both time and money. Buying off-peak plane tickets during the holidays has been especially great on my wallet.

No more long post office lines! (image via Yelp)

Another benefit of a flexible work schedule: the number of hours you work is up to you. While I typically like to work around 40 hours per week, there are weeks when I only work 20 hours — like when a friend is visiting from out-of-town — knowing that I can make up the time the following week. The freedom is awesome, and it’s a great way to build my time management skills!

Con: There’s no external pressure to work

A major downside to not having a boss is that you are the only person responsible for how much you work. The lack of external pressure makes it easy to put work off until later.

I struggled with this at the beginning of my self-employment, and it wasn’t until I started tracking my work hours that I became satisfied with the hours I was working and the amount I was completing. I found that it also helps to have a specific work goal in mind; for example, my goal is to work around 40 hours a week.

My daily Toggl screen, where I log the project, location, and time for each work session

Pro: You choose where you want to work

This benefit mostly applies to those with digital skillsets like myself (I’m a freelance web developer). Being able to work from anywhere allows me to live an efficient lifestyle, especially given that I can tether to my phone if the location I’m working at does not have internet. Long bus or train rides are no longer a loss of time because I’m able to work on them. I can even work when I’m at a park!

Another advantage of remote work is the ability to travel more often and for longer. A perfect example: I’m currently traveling in Southeast Asia and will still be able to work 20 hours this week. As mentioned before, I am also able to tack on a few days to my weekend trips to take advantage of weekday flight prices.

The hipster cafe in Singapore I’m at right now (image via AspirantSG)

Con: Holidays and vacations are unpaid

While self-employment allows for more travel, the downside is that you’re not getting paid for these “days off” anymore. Because of this, I always try to plan for a few work sessions during my travel. I don’t mind this because I love checking out local coffeeshops, but this may be tough for those who like to completely forget about work during vacations.

The no paid leave affects holidays as well. While my salaried friends are always looking to spend the long weekends having fun, I’m conscious of the work hours that I’m losing. My compromise is usually to take off the three-day weekend of the holiday, and then make up the hours either the weekend before or after the holiday.

Con: It’s harder to build out your professional network

One disadvantage that I didn’t foresee was losing out of the networking opportunities that come from working at an established company. When you’re at a company, you not only have access to your immediate colleagues and team, but also to the broader employee roster through corporate events. To meet more people in my field of work, I started going to more meetups but have found it difficult to build long-lasting relationships.

A few months ago, I decided to join a co-working space and have been extremely pleased with the decision. I chose the Centre for Social Innovation in New York, which has been great. They have events designed specifically for members to network and meet each other. (Note: not all co-working spaces are designed for people to meet, so if that is important to you, make sure you do your research before signing up!)

The awesome co-working space that I work out of (image via Art InFact)

Pro: You choose what you want to work on

The power to choose what to work on is the main reason I started freelancing, and I’m happy to say that so far I’ve only worked on projects that I truly wanted to be a part of. It helped that I knew what I wanted to focus on: helping early-stage startups build out their product. This allowed me to highlight the relevant experience in my portfolio, which made it easier to secure the opportunities that I wanted.

In addition, I’m happy that I’ve been able to be selective when choosing which companies I work for. It’s important to me that my work is being used to support society in a manner that I believe in, and because I make the final call, I haven’t had to compromise on this.

I hope you enjoyed reading my thoughts on self-employment. If you’re thinking about the switch, in my opinion the main thing to consider is whether the work flexibility is worth the sacrifices that come with not having a full-time job. It was well worth it for me, but everyone is different!

Have any questions about my transition to being self-employed? Feel free to tweet at me or email me!

Originally published at golmansax.com on September 28, 2017.

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