Pros and Cons of Working Nine-to-Five with the Happy Hour Ladies


Pros and Cons of Working Nine-to-Five with the Happy Hour Ladies

Today is the last Friday of the month and my regular listeners know that on the last Friday of the month, I host a happy hour on the podcast where I gather great friends with me to drink cheap drinks and talk about money topics.

This month on the podcast, I’ve had a theme of entrepreneurship, and we are continuing that theme to happy hour. All of the happy hour ladies have worked traditional nine-to-five jobs and started their own businesses. Today we discuss, as we discuss all things, honestly the pros and cons of both career choices and whether or not we could go back to a nine-to-five job after being entrepreneurs.

What are we drinking?

Melanie from Dear Debt and Lola Retreat — Vodka Martini

Tonya from Budget and the Beach and — Sierra Nevada Pale Ale

Liz, Mrs. Frugalwoods, from — On Vacation

Shannon —  Boxed Rosé

Podcast Notes

  • Tonya worked a nine-to-five job up to 2008. Her goal was to always have full-time work. After that, she was a freelancer until December 2015 and then went back to a nine-to-five job until June 2018. She has been freelancing ever since.
  • Tonya graduated from college in 1992 and her first job out of college was at Ford Motor Company. She was paid terribly and had no benefits.
  • Tonya quit her job to move from Detroit to Seattle. She temped for about nine months before getting a full-time job at Northwest Cable News. It was really easy to find work back then. The majority of her work life to that point was working nine-to-five.
  • Melanie graduated college in December 2006 and worked nine-to-five from 2007 to 2010, in the non-profit sector, at an after-school program, as an arts director. Then she went to grad school from 2010 to 2011 and was working three part-time jobs.
  • From 2012 to 2014, Melanie was working side hustles here, there, and everywhere. Her last full-time job was from 2013 to 2014, which was an events and communications coordinator at a non-profit, making $31,000. Melanie quit that job in 2014, even though she had $40,000 in debt, because she was convinced she could make more. She was right – she doubled her income right away, to $60,000, and she paid off her debt in 2015.
  • Self employment isn’t for everyone, but for those who are stuck in the low-pay trap of non-profits, it can be really helpful. Melanie threw a five-year self-employment party a couple of months ago. This is her longest job.
  • Shannon graduated college in 2000, and her first job was at Bank of America, then a hedge fund, then Bank of America, then Merrill Lynch. In 2013, she had her “aha” of the Financial Gym. There are different growth points for the Gym. She got her first investor in 2015 and her larger investors in 2017. She has been at this for seven years.
  • Shannon had different jobs in that 13 year span, trying to find “the thing”. Toward the end, she had three different jobs in three years, and then she told Bill she wanted to start the Gym.
  • Shannon and Melanie opted to leave the nine-to-five for something else. Tonya didn’t have a choice in 2008. She was working for Vivendi Games as a senior video editor and producer and she had been there for eight and a half years. She probably would have stayed there forever because she was making decent money and she liked her boss.  Her company was bought out by Activision and her department tried to convince them to keep them as a video department, but they didn’t, so the company dissolved and she was let go.
  • Tonya was always interested in being a life coach, and that was in the back of her mind, but she didn’t have any experience and she didn’t know what to do.
  • She had an amazing severance package of six months pay and full benefits for that time, plus she saved her vacation and she had a big chunk of money.
  • The first week, someone who was brought on to help at Vivendi had a huge project waiting for her, like $18,000, for two to three weeks of work. Freelancing was great!
  • However, it was like a tease. She did not have jobs like that all of the time, and it got progressively worse. Tonya didn’t know what she was doing, and she was spending a lot of money. It was the perfect storm.
  • Entrepreneurship is not for the faint of heart. It is a rollercoaster.
  • Even though there are so many challenges, Tonya is not ready to go back to a nine-to-five job.
  • A huge con of going out on your own is the ask. There is a lot of time spent being uncomfortable and asking for the business you need to feed yourself, but you have to ask. If you are someone who struggles with that and can’t push through the pain of it, just know that it never stops.
  • No matter how much you want to be given business and have things thrown at you, Shannon does not know of anyone who started a business and has constant work thrown at them. It takes a while to get to that point. About 99 percent of the time, you need to ask for what you get. It doesn’t matter who you are, it is uncomfortable.
  • Melanie takes rejection personally, because she is the business.
  • Shannon has raised $7.5 million to date for the Gym, and she still struggles with the email she sends out asking for money. She needs to ask, because she needs to pay herself, her employees, and her contractors.
  • If you are a nine-to-fiver, really appreciate how nice it is that you are just given money every two weeks and they are paying the government for you. Be grateful for that.
  • Tonya recently had to cancel a trip Hawaii, because she needs to work.
  • A pro of a nine-to-five job, is that it is not your problem. At the end of the day, your employer isn’t going to go out of business if you wait to reply to an email. If you are on your own, it is always your problem. You are all of it.
  • This podcast was recorded on Labor Day, because Shannon, Tonya, and Melanie were all working.
  • Melanie’s number one pro for being on her own is the flexibility. Everyone knows that working nine-to-five is not a great schedule. No one’s natural energy is sustained from nine to five. Melanie is a night owl and she doesn’t like working in the morning. She usually doesn’t start working until 11:00 am or 12:00 pm, she takes a nap in the afternoon, and sometimes she takes Mondays off to visit her grandpa.
  • Having the flexibility to do that is so much better. She likes going to the grocery store on a Tuesday or a movie during the week. Melanie doesn’t like having to watch the clock and she can have a drink at lunch.
  • Tonya agrees with this as well as no more office politics.
  • As the Gym has grown, Shannon has had less flexibility. She is still the boss, but she has so many people she answers to, like clients, employees, and investors. When it was just her for four years, she got into a rhythm.
  • A pro of being a freelancer is the flexibility, but if you aren’t careful, you could end up working seven days a week.
  • Blogging was a big part of Shannon’s world when she had time on her hands. A lot of blogging happens Monday, Tuesday, and Wednesday. Friday ended up being her Saturday, because on Saturday and Sunday she would write blog posts for the next week.
  • Every other Friday is held for Shannon’s free day. She wants it to be a Saturday for her, but lately her free days have been blocked.
  • In the beginning, almost every Friday Shannon and her mom would go out for drunch (drinking lunch). Now that free day doesn’t happen as much.
  • Melanie misses health insurance the most. She spends $358 per month on the cheapest, most crappiest insurance. It is confusing and hard. The taxes, retirement, and health insurance are the worst. She misses having sick time and vacation time.
  • Vacation time it isn’t only time you need off work to decompress, it is also time that you aren’t making money.
  • Right now, Tonya isn’t making anywhere near what she was making as a full-time employee. The constant adjusting and time tracking is difficult. She needs to make sure she is staying focused and assess if the jobs she does are working for her.
  • Shannon misses things being someone else’s problem. When the computer doesn’t work, it is IT’s problem, or if she has an issue with health insurance, it is HR’s problem. Even when it is just you, everything is your problem.
  • When Shannon was on her own, her website was hacked. She had to figure out how to fix it. You have to do everything. As her team grows, she is getting better at delegating.
  • Another pro of being on her own is that Melanie likes being able to execute a vision of what she wants her life to look like and what she wants her schedule to look like. Lola Retreat is difficult to produce but very rewarding to see it come to life.
  • A pro for nine-to-five is having people around you who could be a mentor for you.
  • As much as office politics suck, it is nice to have someone who is going through what you are going through.
  • Tonya wonders if it is worth it to pay for a business coach. It feels like you are on an island by yourself. Even though you have fellow freelancers around you, it would be helpful to have someone help you hone your vision into the right avenues. There is so much experimentation and it might not work.
  • The highs are really high. If Tonya is helping someone with their company, and she is making a bigger difference than if she was working for another company.
  • Shannon was uncomfortable being in the box (working for someone else) when she saw her co-workers who had been at the company for 25 years lose their jobs in 2008.
  • There is nothing better than having a direct result to your actions.
  • Melanie doesn’t see anything that would coax her back to a nine-to-five job. It would have to be a really great job, but she doesn’t know what that would look like.
  • Tonya cannot imagine a job that would get her back to nine-to-five.
  • Shannon doesn’t know if she could work for someone else again. She has been the boss of other people for three years now. She has been the problem solver and the implementer.
  • Shannon is hiring 25 new people. The Gym is going from 24 employees to 49 employees.
  • Shannon was recently featured in Shape Magazine, in an article called How Shannon McLay is Bringing Financial Fitness to all Women.
  • On October 6, Shape is doing an all-day event in NYC. Shannon will be on a panel called Change Makers: Women who are proactively addressing an issue to affect change.
  • If you are thinking of taking the leap into freelancing, Tonya recommends having as much money saved as possible. It will be that much less stress.
  • Melanie says to learn as much as possible in those first couple of years and build relationships and your reputation. Once you have a network, you have some leeway to be a human being and not freak out when things happen.
  • Shannon recommends playing nice on the playground. Always be the better person, because you never know when that will come through.
  • If you want to start something, have at least one year of expenses saved up and be really passionate about what you choose to do. You are going to work a lot of hours and, if it feels like work, it is going to be really challenging.
  • Shannon is passionate and motivated by the work and the thing she is building and it sustains her through the rollercoaster and long hours.

TAKEAWAY: My biggest takeaway is that the entrepreneurial journey is truly not for everyone. If you have a strong stomach and a willingness to hustle, despite the ups and downs, you may actually find out, like I did, that it is the only way you could ever work again.

If you want to work with my team at the Financial Gym and find out what it takes to start a business, remember that Martinis and Your Money Listeners get 15% off Financial Gym services. My financial trainers have seen it all. No matter where you’re starting, we have the tools and resources to get you where you want to go. So head over to, or send friends to,

If you have any topics you would like for us to talk about during happy hour, please feel free to email me at or tweet to me at blonde_finance or join the private martinis and your money Facebook group and let us know. Until next time, take care!!

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