TWT News

TWT S2 E5: Insurance and The Gig Environment

We can insure you that you’ll feel inspired by the people you meet in this TWT episode. In this segment, Jackie visits Markel Insurance to learn about an app they work with called Verifly. This app allows people who have a side hustle to ensure their specific projects by the day or week at a lower rate. This way, for people who have a side hustle, you only need to pay to be ensured for days or months (or hours) that you actually need the coverage. From there, Jackie goes on to meet two side hustlers, Mike and Todd, and she gets to see how the new insurance technology works for them and their businesses.

According to a 2017 Bankrate study, 44 million Americans have a side hustle. Meanwhile, The Hustle found that the average side-hustler spends 11 hours per week on their secondary work. For anyone looking to start or maintain a side hustle like Mike and Todd, here are some tips to help:

TWT Season 2 Side Hustle 1
Choose a side hustle you’re passionate about

As we learned from the awesome entrepreneurs in this episode of TWT, your side hustle should be something that you’re passionate about. Even if you’re someone who loves your day job and just wants to make some extra money, it’ll be so much easier to stay motivated and disciplined if your side hustle encompasses another of your passions. You may consider yourself a go-getter, but when you’re already working 40+ hours per week it can be difficult to add on an extra endeavor. But, if your side hustle is something you consider fun, it becomes a therapeutic hobby that’s easy to stick with.

Scheduling & Organization are key

When you’re working full time and trying to start or maintain a side hustle, it can be easy to get disorganized when it comes to scheduling. Depending on what second job you’re pursuing, it could involve blocking off specific dates/times multiple times per week. In addition, and possibly more difficult, it could be a job where you only need to work a few hours a week on your own time frame. You may initially believe this is the easier option, but for some it can be harder when there isn’t a set date/time that a task needs to get accomplished because this can so easily lead to procrastination or just forgetting the task entirely. Our recommendation is to keep a detailed calendar of what needs to be done, even for tasks that just have a due date. If you’re actively setting aside a certain night every week for your side business, this will alleviate a lot of stress and procrastinator’s panicking later on.

TWT Season 2 Side Hustle 2

 Learn to delegate when need be

If you’re starting your own side business, you’re likely someone who’s very independent and prefers to handle things themselves. The problem is, when you’re already working full time, doing all the work yourself can be trying. In addition, we all have our own strengths and weaknesses when it comes to running a business. For example, let’s say you’re working on building up your freelance writing clientele. You may be good at the actual writing side, but you have trouble establishing a social media presence to promote your work. Much as you may want to just do it on your own, bringing in someone to help alleviate some of the workload or with a specific area of expertise is definitely worth it.

Create realistic goals

When you’re pursuing something you’re passionate about, it can be easy to get carried away with your ambitions. But, if you already have a full-time job, the last thing you want to do is pour every spare second into a side business and end up burned out and miserable. Decide on a reasonable amount of time that you feel you can set aside for a side business per week and create realistic goals for the long-term.