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How to Use Multiple Side Gigs to Achieve Financial Freedom

Updated: Oct 29, 2022


Note: transcription provided by Otter.AI, which is a technology company that develops speech-to text transcription and translation applications using artificial intelligence and machine learning.


Christopher H. Loo, MD-PhD: On today's show, we have Dr. Hisla Bates. Dr. Hisla Bates is a board-certified, Harvard trained Pediatric and Adult Psychiatrist with over 20 years of experience in the diagnosis and treatment of severe mental illness and managed care. She's had additional training in Primary Care Internal Medicine at Yale. Her General Psychiatry training was completed at Mount Sinai in New York City. She completed her Child and Adolescent Psychiatry Fellowship at Harvard Medical School's Massachusetts General Hospital in the Department of Psychiatry program.

She's also studied with Dr. Tal Ben-Shahar and is certified in positive psychology from the holding Institute. She has an integrative and holistic approach to the treatment of mental illness. And she uses tools in Mindfulness, Positive Psychology and the expressive and creative arts, working with children and adults. She is the co-chair of the Art Committee for the American Academy of Child and Adolescent Psychiatry. She is a Parsons School of Design Graduate in Fashion Design, and an artist and printmaker who enjoys photography and filmmaking as well.

She utilizes all of her skills in her practice as a psychiatrist and coach. And so, in today's episode, you're going to hear all about how she developed these multiple streams of income on her side through real estate, as well as how she integrates all of her creative endeavors and pursuits outside of psychiatry as a coach and as an artist. So without much ado, here is Dr. Hisla Bates.

Dr. Hisla Bates, MD: When I was doing my fellowship at Harvard, in pediatric psychiatry, I just knew that I wanted to purchase a condominium in Brookline, Massachusetts, because I was told that was where all the great schools were. And raising my daughter as a single mom, I wanted her to, of course, have a wonderful education. So I didn't know a lot about real estate, but I started reading books about it, and decided I would purchase my first condominium. It had to have certain criteria. It had to have an outdoor space. And it had to be in my price range.

At that time, it wasn't very high. And so it was a bit of a fixer upper. And I fixed it up and lived there for probably about three to four years and then sold it for a nice profit and went on to purchase a second one. And then a third, and similar story. And with each purchase, there was more fixing, so to speak. So I renovated two kitchens, two bathrooms. And then I moved on to purchasing a single family home. And that was outside of Brookline, and I completely renovated it. So it was a gut rehab. And it was one of the largest undertakings that I've ever done. And lived there for about five years.

I sold it, and with the equity that I had earned from that home, I essentially had financial freedom. And I was able to pay off my daughter's college tuition, which was well into the six figures. And to live debt free, and start doing a lot of the things that I had put off for a very long time.

And so for the past two and a half years, I have taken lots of courses, educated myself in areas of interest in the arts and coaching, in entrepreneurship. Traveled a lot, went to a lot of conferences, and just really explored a lot of areas that I hadn't before. And, I moved from Massachusetts to New York, which was always a dream of mine to to come back to New York City and to be here.

So, real estate I'm very grateful for. And since I've been in New York, I purchased a duplex. And so my next plan is to start doing some short term rentals. And I'm looking forward to that experience. And I hope over the years to continue to purchase real estate and now that my daughter's an adult, I feel like I have more time to invest in that area. So I'm excited about the possibilities when it comes to real estate.

Christopher H. Loo, MD-PhD: That's amazing. A lot of the physicians that I talk to and that I collaborate with say a very interesting quote, which is, “You cannot work your way to financial freedom, you have to invest it.” So a lot of it was through real estate and through equities. But real estate is really highly popular among physicians, because it has so many advantages, which you described. So it sounds like your real estate strategy was over time, it's not like you just delved right in, you did it on the side. You learn a little bit about renovation and improvements, and you just sort of bought slowly accumulated your wealth. And then and then you sold it and it helped you to get out of debt and help pay for your daughter's college education was really interesting.

Dr. Hisla Bates, MD: Well, the reason why I did it slowly was number one, I was a single mom and I had just finished my fellowship. I don't come from a family that has had resources or money to help me. So I have to do it all on my own. And, trying to raise a child and be a real estate investor. Honestly, at the time, I didn't know how to do it other than kind of the slow boat, the slow, slow method. And I'm still kind of doing it that way. But I feel like I like to be in control. So, I've learned a lot along the way and I just love it. So I'm constantly looking at real estate.

Christopher H. Loo, MD-PhD: Yeah. For the listeners out there, you hear all these stories, they became a millionaire in less than a year and but, there's very, like, there's a good book, which was just, slowly accumulate your wealth over time. And usually at the end of eight or nine or 10 years, you will have accumulated, so, you don't have to do it all in one sprint. And you can also do it in your spare time. You have a lot of physicians, they invest on the weekends, they look at deals at night after their kids are asleep. There's so many different timelines, different strategies.

And now you're doing a lot of creative things, looks like you're doing a lot of creative design. You're involved in the arts, and then you're also coaching. So tell us more how financial freedom allows you to do different things.

Dr. Hisla Bates, MD: Before I had financial freedom, I was working 70-80 hours a week, I was working like a dog, like everybody else in medicine. And, I was pretty miserable, actually. And I had this desire to paint and, and just go back into the arts in some way, because I had pushed all of that aside through my training and residency. I always felt like I never had enough time to do it. And, I started buying the art of other artists, and admiring their work.

I actually moved to Arizona, and I was planning on having an art studio in my Casita. And I had this dream of having this art studio and living in Arizona, and having a simpler life, so to speak. But then I went to Arizona, and it wasn't so simple. And I had no community and no network. And so I quickly moved back to Boston.

And I found, when I moved back to Boston, an art community. A community of other painters, printmakers and so on, and I stopped buying the art of other artists. Because my daughter said to me, “Mom, I think you can do that. I think you can do [the art that I was about to buy],” which was significant. And I started painting and printmaking. And it all felt very new to me because I was a fashion designer. I know how to do fashion illustration, but I'd never really had any experience with oil paint and canvas. And so that was all new for me. And I felt very vulnerable.

But over time, I became more comfortable with it. And I dedicated an evening a week to going to the studio. And we all met as a group, there were about 10 of us. A mix of people, I was the only physician there. But I made sure that I went on a weekly basis and that really nourished me and nurtured me in a way, and I really started to feel more joyful again. And, and it I just think I became a better parent and a better physician because I felt more connected to myself, and to everything else.

So I then went on to submit my artwork to juried shows, got into a few juried shows, the Boston Printmakers Biennial, which is a big printmakers show in 2011, selling my work. And so this part of me, this artist, artistic part of me just seemed to blossom during that period of time.

Christopher H. Loo, MD-PhD: That's so amazing. I'm not sure if you've heard of Dr. Susie Sharpe, I interviewed her on my podcast, and also Dr. Olapeju Simoyan, she's up on the East Coast. She's also an artist.

Dr. Hisla Bates, MD: I’ll have to listen. I interviewed Susie Sharpe as well. And her story, of course, is very fascinating. And my podcast is actually based around creatives and physicians who are using the arts in ways to heal themselves.

Christopher H. Loo, MD-PhD: You mentioned so many interesting things such as being vulnerable, and because medicine doesn't allow you to, it's like an assembly line. And you're not allowed to be creative. But the thing is, as humans, we're creative beings and we're creative creatures. I also loved your reference to just showing up, just being consistent.

When I started blogging, nobody listened. It was more of a creative outlet for me. And, it's since grown. And a lot of people are interested in what you write about. And, whether or not you make money off of it or monetize it, it's doing it for the sake of doing it. And I think a lot of people would be interested in contacting you or meeting you. So what's the best way to get in touch with you and follow you on social media?

Dr. Hisla Bates, MD: Well, one way is to go to my website, and get on my mailing list. I don't email people very often so you won't be bombarded with tons of email. Because I don't like email very much. I'm also on Instagram quite a bit and Clubhouse. So that's another way to get in touch with me. And I started a Facebook group for Physicians and Healers who are interested in the Arts. And you can sign up through my Instagram. Just tap on the bio and you'll see a link to the Facebook group. And, yeah, reach out to me. I love speaking to artists. I love also speaking about real estate and am happy to share.

Christopher H. Loo, MD-PhD: You've given such an incredible story. And you've talked so much about creativity. What's one less piece of advice for the listeners to take away for the show?

Dr. Hisla Bates, MD: Well, I'd like to say, tap into your creativity, if you have any kind of yearning to paint or to draw. You will feel much more connected to yourself and your patients. It'll make your life much more joyful. And, don't leave parts of yourself out because you want to focus only on medicine. Open yourself up, become vulnerable, and enjoy, have fun.

Christopher H. Loo, MD-PhD: Those are beautiful parting words of advice. Thanks so much for your time on this show, and we look forward to hearing about your future successes.

Dr. Hisla Bates, MD: Thank you so much for having me. It was a pleasure meeting you and speaking with you, Dr. Loo.

Christopher H. Loo, MD-PhD: Many thanks again for being here. If you’re new, you can find me online at Christopher H. Loo, MD-PhD, where I have links to other episodes or links to online resources that will support you on your financial literacy journey. I’ll see you there in on next week’s show. While I bring you thoroughly vetted information on this show regarding a variety of financial topics, I cannot promise you a one size fits all solution. This is why I caution you to continue to learn. Educate yourself and seek professional advice unique to your situation. If you want to talk to me, I welcome it. Please reach out via my website or email at I read and personally respond to all of my emails. Talk soon!


Editor's note: This transcript has been edited for brevity and clarity.

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