Welcome to Michelle is Money Hungry, I’m your host Michelle Jackson and I focus on holding financial conversations that lean into social equity, policy and access with a splash of pop culture. My goal is to lead these conversations with empathy and help both my listeners and myself learn more about money along the way.
For the next week my guests and I focus on when American women decide that they want more in their lives. Interestingly, many of the conversations center around going into entrepreneurship. With that in mind, I do want to say that my guests and I aren’t necessarily encouraging you to go into business.
Instead, this conversation in my mind is a reflection of the policies that aren’t in place here in the United States. Policies such as paid parental leave, generous paid sick leave. Or, just having a degree of flexibility and autonomy over your days so that you can run an errand, schedule a doctor’s appointment or take your kid to ballet or help your parents out when things come up. I often wonder how different American life would be if we had some of these policies in place. Would the choices we make be different?
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HARLOW
When I moved into digital entrepreneurship, I found myself collaborating with brands, doing 1099 work and needing to send out invoices and set up systems to keep my business organized.
It has been an ongoing process to find the right tools and systems for me. I’m so excited about a new tool that I now use that allows me to invoice clients, set up tasks, and even track my time as I work on tasks. I also use it as a CRM or client relationship management system. What’s the tool’s name?
I’m so obsessed with Harlow and am so excited that Harlow has partnered with me to bring the conversation around women wanting more personally, financially and professionally to life. Harlow is a woman-owned business, designed by former freelancers who understand the challenges of keeping creative businesses organized. I love how responsive the team is to my questions and emails which is a big deal as they continue to improve and refine this new tool. If you’re looking for a comprehensive system to organize your invoicing, client management and keep yourself organized I encourage you to give Harlow a try. I’m also a proud affiliate. Go to michelleismoneyhungry.com/harlow to check it out.
Show Notes
Jen Ruiz-I’m a lawyer turned full-time travel writer, content creator, author and digital entrepreneur (Jen on a Jet Plane)
Michelle-How did you do this?
Jen-It was a slow trajectory. For me, it was a lot of trial and error. I actually launched my first blog because I wanted a creative outlet and found that I really enjoyed writing. I just started writing to do something fun and challenge myself during the day. I actually rebranded twice. It wasn’t until mid-2016 that I landed on Jen on a Jet Plane
Michelle-What did the people around you think about this project? How were you able to pursue your dream life? This is a very vague and broad question.
Jen-The same core skill sets that drew me into trial law, I used in my content.
Michelle-You were doing things like flying a plane. Were you seeing other women dreaming in the same way?
J-No, I was in South Florida and the focus was more on status symbols. It felt like I needed to have a particular car, or a particular purse. It never felt authentic to me. I remember thinking, I worked so hard to get here and this kind of sucks. I realized that I wanted to do more things for myself than for other people. Every year I decided that I would be traveling for my birthday. I would never regret going somewhere. It was a way for me to mark my life in a meaningful way.
M-American women are often conflicted about pursuing things that bring us joy. What did you wish your friends understood about why you wanted to do this?
Jen-I wished that my friends understood why I enjoyed traveling on my own. It wasn’t a lonely experience. I’m eating and drinking what I want (Butterbeer) and I’m having the best day and this is my “work” The only person you’re looking to please is yourself.
Michelle-I love that you use the word “selfishness” Are we being selfish for wanting more? My grandma has on more than one occasion said that I’m selfish. I think that there are some generational tensions around designing a life that allows you to thrive. How did you embrace this totally different way of being, how did you decide that you could thrive in a different way?
Jen-It was…interesting and it wasn’t something that I had been taught. I had spent my whole life worrying about getting into a good college and trying to meet these external markers of success and I realized that I spent my entire 20’s living for other people. Especially in the law space because you’re spending so much time fixing other people’s problems. I handled almost 700 cases by the time I was 29 and not focusing on who I was. So I decided to do 12 trips in 12 months before I turned 30.
Michelle-Me, me, me!! How did you have the time? How were you doing this?
Jen-I didn’t have the time. I worked for one company that made us work on Christmas Day.
Michelle-The Christmas Day?!
Jen-Yes, and they threw a pizza party too. I was like I just want to be home and I hate it here. I remember that feeling that I couldn’t believe that they thought they were being generous. That was part of why I wanted a job that gave me more time and space. Then, I worked at another private firm and the same issue came up. I switched to public service but I had public holidays. So, I had more time available. I also worked normal hours at this non-profit firm.
Michelle-What do you want other Latinas to think about if they’re thinking about reframing and redesigning their lives?
Jen-Ask yourself what you want to do. People want to protect you, but those concerns also are framed from trauma and fear for you. Most of our parents work really hard. When you do what you’re called to do the money will come later.
Michelle-Could you share what this transition was like? How did you prepare financially from doing traditional work to what you do now? I love that you shared that it wasn’t overnight.
Jen-It’s been 8 years and 4 years of doing it full-time. I know that at some point someone is going to say I was an overnight success. But, it’s more about taking baby steps. One of the big things for me was to a travel blogging conference (my first one) . I was feeling some kind of way about it because it was in Huntsville, Alabama and it cost more than some of my European trips. I felt like this cost more than what I normally spent. I noticed a difference from when I attended law conferences that I normally wanted to skip (the sessions). I hated all of the legal events that I had to attend.
Michelle-It’s so funny to me there’s a moment that it’s clear you’re not supposed to be where you’re at. I love that you decided you would be first on your list.
Jen-Even a 24 hour trip, a day trip can be impactful. I was invited to go to Epoch and experience a live taping of The Chew. I got into the park for free. It’s in Florida where I live and I’ve been there many times. I realized that anywhere can feel like a travel destination to someone else.
Michelle-For someone who’s listening and is thinking “I hear you Jen, but money is tight and I’m not sure how to approach this.” Also, how did you earn your way out of the old job?
Jen-I flew that plan by getting on Groupon and paid around $100 for that experience. I also would log into Fort Lauderdale on the Cheap website so that I could get the reduced price. There are definitely a lot of free activities to participate in. People kept asking me about how I was going to all of these places. I went to the library and learning about travel hacking both reading and podcasts. I sign up for flight alert programs, my favorite is Scott’s Cheap Flights (I’ve used them for over 5 years). Another way is budget airlines. I flew to Iceland on WOW Air. I almost look at budget airlines as a layaway structure. I do not have any loyalty to any airline. I really don’t care, I want to fly the airline that gets me there the cheapest. I will fly Frontier or Spirit. If Spirit has a $20 flight, here we go. If you know you have set dates and a set location, points and miles come in here. As a Hispanic woman I was very nervous about this. My mom told me my whole life that credit cards were for irresponsible people. My first card experience was a disaster. I took out a Jetblue Card.
Michelle-How did you earn your way out of your old job into your new career.
Jen-First, in February I realized I needed more money so I got a job teaching English online. I emphasized that I was an attorney and had a degree. This company was in China and I knew enough about the culture to emphasize what would get my foot in the door. The students would be awake when I normally sleep. I would teach every weekend all through the night. That was hard but I made $1800 that month and it felt like I was rolling in the dough. I used that money to fund my travels. Waitressing was also a backup. In March, I self-published my book and it became a bestseller, it won awards, I wasn’t rolling in the dough but it was proof of concept.
Michelle- For those people who would like to follow Jen and would like to learn more about the business of online entrepreneurship
Follow Jen
Website: https://jenonajetplane.com
How to Make Money as a Writer (Book)
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