Happy Hour Crew Talks Entrepreneurship and Side Hustles
Today is the last Friday of the month, and my regular listeners know that on the last Friday of the month, I host the happy hour on the podcast, where I gather great friends with me to drink cheap drinks and talk about money topics. This month, I’ve talked about side hustling and entrepreneurship, a subject matter that is very near and dear to my heart as I’ve been on an 11-year entrepreneurial journey at this point. My friends join me today to talk about their entrepreneurial endeavors and the pros and cons of it vs. a 9 to 5 job. As always, I loved hearing what my friends had to say on the topic.
What are we drinking?
Melanie – 0 Sugar San Pelligrino Lemonade
Colin – Martini – Cinnamon Apple Martini
Shannon – Ketel pre-mixed Cosmo
Podcast Notes
Personal Journeys in Entrepreneurship and Side Hustles
Shannon, Colin, and Melanie all have experience working for a traditional employer and being self-employed or business owners. There is no right or wrong option, but about doing what works best for you, your goals, and your lifestyle.
Shannon wanted to start The Financial Gym as a side hustle, but her employer would not allow it. She had to make the tough decision to leave that job and pursue The Financial Gym full time. She is thankful for her path but would not recommend it to others.
Melanie has been a full-time freelancer for many years. Some aspects are great, while others can be a challenge. She loves the flexibility of being able to create her own schedule and being able to work from anywhere. Having to directly produce work to make money, rather than having a salary, means there is a constant grind, which can lead to burnout.
Colin has experience being a freelancer and working a full-time job. After being laid off, he’s been freelancing again but is still looking for other employment opportunities. Colin thrives in structure and with a team, which is why he prefers a full-time job over being a freelancer, but he would be open to either option with the right company.
Challenges of Freelancing and Self-Employment
Running a business is a lot of work, especially in the early stages, and burnout is a real risk. If you do not have the drive or work ethic to keep yourself motivated, it can be challenging to be a freelancer.
Freelance work can be inconsistent. While the flexibility can be great, the lack of paid time off and benefits can be stressful. Freelancing also requires a decent amount of unpaid labor, like invoicing, bookkeeping, and other logistics.
Freelancing or being a business owner can be extremely isolating, especially if your work doesn’t require you to be social. If you thrive in a team environment, this solo lifestyle can be challenging.
As an employee, you have certain protections under labor laws. If you are a freelancer or contractor, there are far less protections. Companies often try to take advantage of people by paying them as contractors but requiring them to work as if they were employees.
Advice for Aspiring Side Hustlers / Freelancers
To have a sustainable business or freelance career, setting boundaries and aiming for a healthy work-life balance is important. There will be a lot of work, but if you do not take care of yourself, you will burn out.
If you want to leave your consistent job to start something on your own, build an emergency fund bigger than you think you’ll need. This will help you budget for sick days, vacation time, and slow periods in the business.
Even if you don’t think your side hustle will grow, get organized early. Track your income and expenses and find a tax professional who understands your work. Don’t wait until it’s time to file taxes to look for an accountant or CPA.
Know yourself and your energy levels. Freelancing is a roller coaster, and you need to be prepared for the unexpected. Sometimes, you don’t know if you like something until you’ve tried it out, which is why it’s always great to start with a side hustle.
Takeaway: My biggest takeaway is to listen to your inner voice. If you’re being called to start something, whether it’s a side hustle or a full-blown company, there’s a reason you feel that way, and you need to lean into it. Your journey may not be about creating a successful company, it could just be about the lessons you’ll learn along the way. Either way, trust your gut and don’t be afraid of the big risks.
Connect with The Happy Hour Crew
Melanie Lockert: melanielockert.com
Colin Becker: @iwillbecolinyou & colinbecker.com
Shannon McLay: Founder & CEO at The Financial Gym
If you have any topics you would like me to cover on this podcast, or if you’d like to get in the financially naked hot seat, I encourage you to email me at Shannon@fingyms.com or join the private Martinis and Your Money Facebook Page, and let me know what you want to hear.
As many of you know, other than running this podcast, I’m the founder and CEO of The Financial Gym, and we are celebrating 10 years of this journey. Now more than ever, I see the importance of the work we do every single day. Rising inflation, the return on student loan debt, high-interest rates on loans and mortgages, and volatile stock markets make it a time where, now more than ever, you need a best financial friend to help you make the best choices along the way.
At Financial Gym, you get paired with a Certified Financial Trainer, who we call your BFF. Our team has coached clients through every financial season, whether they were living paycheck to paycheck or headed into Financial Independence and Retirement. As a reminder, we work with individuals, couples, or business owners.
The exciting news of 2024 is that Financial Gym now has a sister company, FG Advisory Services, available for people looking for more traditional financial advisory services like asset management delivered by a team that looks and behaves nothing like a traditional financial advisory services company. We literally have a solution for you, no matter where you’re starting from. So what are you waiting for? Head over to or send friends to financialgym.com to get started today. Our warm-up calls are free of cost and judgment, so you have nothing to lose.