Forward in Heels with Jenny Maenpaa


Forward in Heels with Jenny Maenpaa

If you’ve listened to the show before, you know that mental health is a topic that is really important to me. I always say that without physical, mental, or financial health, what are we doing this for. I view all three as equally critical to allow us to live our best lives.

Even though May is Mental Health Awareness Month, I wanted to kick off my discussion in April and speak to a mental health practitioner to answer all of the questions I’ve had around my own mental health, like how do I find the right therapist? How much should I pay? Can I negotiate? and more. Joining me to answer my questions, and hopefully yours, is Jenny Maenpaa, Psychotherapist and Women’s Leadership Coach and Founder of Forward in Heels. Jenny is a long-time friend of the Gym and I love her perspective on all things mental health.

What Are We Drinking?

Jenny — Pinot Grigio

Shannon —  Chardonnay 

Podcast Notes

  • Shannon knows Jenny, because she is a client at the Financial Gym.
  • Jenny’s trainer used to call her the billions woman, because of her job at the time.
  • In college, Jenny was a psychology major, because she thought it was interesting to study how people interact with each other.
  • She wanted to be a criminal profiler in college and she took some forensic psychology classes. 
  • After she graduated, she found out quickly that you cannot really do anything in mental health without a masters degree, so she went back to school and earned her Masters of Social Work (MSW).
  • Jenny always thought she was going to be in social services and work for the government. She realized quickly that she didn’t love criminal profiling, because you have to wait until bad things happen to people before you get information.
  • She worked in victim’s services for a while and didn’t like to feel as though she was a bandaid on the end of it. She decided to go more into prevention.
  • After she finished her masters degree, she worked in juvenile justice in a high school with over-aged/under-credited students. These are 18, 19, and 20 year olds who are not able to graduate because they don’t have enough credits. This happens if they’ve had a lot of interruptions in their schooling due to behavior or instability in their homes.
  • She was really aligned with the mission of the school, but the vision and mission didn’t align with the practices. People had good goals and wanted to do well, but they weren’t trained in leadership. When a bad boss is in physically and emotionally dangerous and taxing circumstances, that burns you out quickly.
  • A lot of the kids hadn’t learned emotional self regulation, so there were a lot of fights and challenges within the community and within the school, and the leadership didn’t know how to work with the mental health professionals to understand that they were also having experiences. 
  • Jenny worked in a lot of circumstances where therapy was forced on people and that is not what works for most people. 
  • In the spring of 2015, near the end of the school year, Jenny was burning out and she didn’t think she could do the job anymore. She was having her own trauma symptoms where she was waking up in the middle of the night in a cold sweat, her physical body would change when she walked into the building, and she didn’t know what to do. She only knew how to do therapy in that type of environment.
  • Jenny’s coworker asked her if she had ever thought about coaching, where you use the same skills you learned as a therapist but work with people who are high functioning, in a job that is high-powered, and they come to you by their own choice.
  • Jenny left the school at the end of the school year in 2015 and she enrolled in a coaching program. She knew how to be a therapist, but she didn’t know how to run a business.
  • Jenny loved the program and she found it added a counterpart to social work, because she found that coaching is rooted in people reaching for their dream lives versus therapy that is fixing a problem and getting to a level of maintenance.
  • So many people could benefit from therapy, even if we think we are okay or good, by having that impartial and unbiased person who is trained. They can add an extra perspective.
  • Jenny liked that she could combine the clinical part of social work with the idea that you can dream a big life for yourself no matter where you are starting.
  • One of the reasons Jenny loves the Financial Gym, is because when she started going there, they made her feel like there is no financial problem that they can’t fix. It is all about getting out of debt and financially preparing for a life that you want to live. 
  • The motto of the Gym is “What are you working for?”
  • Many people have limiting beliefs of what they can do, and it is the financial trainers’ jobs to tell clients new stories. This is similar to what Jenny does. 
  • When asked what type of therapy she does, Jenny says she does a combination of psychodynamic (Freudian stuff, your past, parents, etc.) and cognitive behavioral therapy (rewriting the narrative we’ve come to accept).
  • Shannon finds the second school of thought, cognitive behavioral therapy, to be helpful to her.
  • If you do just the psychodynamic therapy without changing the narrative you’ve come up with, it isn’t that useful. Going back and examining the trauma or pain without any action is just navel gazing. 
  • A financial example would be someone who felt like there was never enough money as a child. Their parents always made it feel like they were pinching pennies to afford to eat and now the person has in their head that there will never be enough, even if they make six figures. You can examine that, but then figure out how to rewrite the idea that there is never enough by looking at the evidence and the facts. Look at the behavior and then the facts – look at the bank account and expenses. That fear is rooted in childhood, but now the person is in charge of changing that story. You can understand where the idea comes from. The pain and the experience is real. 
  • You have to find a therapist or a coach that works with you. If you are someone who wants to understand some of the past traumas, relationships, or patterns, and you do want to spend time on that, you will need to find someone who does more psychodynamic work.
  • Finding a therapist is like dating. You don’t go on one date one time and say dating is not for me because that person is not right for me, but we do it with therapy all the time. Many people go to therapy once and say it isn’t for them, but there are thousands of ways to do therapy. 
  • If you don’t have your physical, financial, or mental health, what are we all doing here?
  • There is such friction to find the right person and the right type of therapy. It is a lot like online dating, because you can filter for the types of things you are looking for.
  • The biggest clearinghouse of therapists is It is where all therapists are listed by their degree and credentials, and you can search by ZIP code and/or specialty. Each therapist has a short bio that they wrote. They should have a website and a free consultation call or visit.
  • For people who think they can’t afford it, this is an investment. It is like brushing your teeth — you want to brush your teeth every day, even when your teeth feel fine, because when you stop brushing, that is when things get bad.
  • We go to the gym and we look at our finances for our physical and financial health, and we need to do the same for our mental health. 
  • If you think you can’t afford it, you may find that you are spending money somewhere else to cover up what you are feeling and not addressing the issue.
  • Jenny has worked with people who have high paying jobs that they hate and, because they are so unhappy, they do a lot of online shopping. When the bill comes at the end of the month, they realize they need the job to pay for their shopping. Once they start to examine why they are unhappy and make a change, they break free of the cycle, and it frees up money to spend on what they actually want. 
  • Other people do this with drugs and alchohol. 
  • Seventy percent of the population live paycheck to paycheck and there are a lot of emotions around money. When you address some of the emotional challenges, it frees up the financial resources.
  • For some Financial Gym clients, they figure out the financial aspects first and then figure out the emotional stuff. It is all entwined. 
  • Many Gym clients say their sacred cows are travel, family, time with friends, and gym memberships, and their top spending categories do not reflect what they are saying they value. It is because of the disconnect. It is easy to spend money.
  • There are plenty of great therapists that take insurance. 
  • Jenny doesn’t take insurance. She has worked for managed care companies and when you sign up for health insurance, you sign away some of your privacy, because you are agreeing a third party can access your records so they can determine if it is medically necessary.
  • Therapists who take insurance get paid a lower rate, which means they may need to stack their schedules to have enough people to see to break even. On the insurance side, they can deny treatment, limit sessions, and see all of your records. The health insurance company’s bottom line is financial, not your mental health.
  • It is important to keep in mind that therapists are required to do continuing education to specialize. Every two to three years, they need to do more and more specialization, because nobody is really great at being a generalist. When you get into more specialized fields, the cost goes up. 
  • If you are going to a therapist for post-partum depression, that is a short-term commitment. That is not someone you will see throughout your lifetime. After 12, 15, 30 sessions, you will feel like you’ve got the tools you need and you won’t need to come back. 
  • There is no set number of appointments that is going to be right for everybody.
  • There is something to be said about the chemical changes in our brains and bodies as we go through life. People may go through therapy, have the toolbox, and think they don’t need therapy anymore. That sets us up for failure, because we get mad at ourselves if we can manage it. You learned the technique, but there is still so much that is not known about the brain. Information is evolving. 
  • There are some therapists that reserve a certain number of slots for a sliding scale fee. Most therapists that Jenny knows who do not take insurance do a sliding scale for the fee. If you have been seeing someone and there is a built in, ongoing relationship, it is Jenny’s ethical obligation not to just say sorry that you can’t afford it. It isn’t just wrong, it is something she could be sanctioned for.
  • Her requirement is to work with the person to see if there is space they can free up in their budget, maybe do a sliding scale, or refer them to somewhere that is a “warm transfer”, where she knows the therapist, it is the right specialty, and she can foster the transition. 
  • Ask about sliding scale and ask about negotiating. There are a lot of regulations in mental health, even more so than financial services.
  • Therapists are not allowed to barter and they can’t charge different rates for different people, because it has to be a standardized set. Sliding scale is allowed, because it is standardized: X number of people can pay Y amount.
  • Mental health professionals are bound by certain rules and most would love to give therapy for free, but it is a service they are providing and they had to get advanced degrees to do the work. It isn’t like law or finance where you expect a return on the investment. Therapists tend to make the same amount of money post-degree as they did pre.
  • It is hard because you do spend time and invest in the relationship, and sometimes people need to stop because of financial reasons.
  • Many people think about therapy only when they are in crisis mode.
  • Last April and May, Shannon had a difficult time where she didn’t want to be the boss anymore. She sought therapy and she was financially strapped at the time, because it was right when she was trying to sell her house. She looked for an online solution, but she prefers to talk through it, not email. Oprah’s supersoul conversations and a gratitude journal got her through that time, and now she feels good, but it is not always a good idea to wait for a crisis.
  • Jenny finds that waiting is the most detrimental with couples. Nobody goes to therapy until it is too late. So many things get in the way and the fixable things become unfixable at that point.
  • Shannon has clients that have been with her for years and it is like their therapy. She has other clients who have been with therapists for years. Having a disinterested/interested third party is critical to invest in the life you are living. 
  • No matter how you feel mentally, you are just one issue away from things falling apart.
  • There seems to be this idea with millennials that nothing is ever good enough. Nobody reaches the pinnacle and says they are satisfied. It is all about the next thing. When there is never an end game, and you will never be happy with whatever you accomplish, you are just constantly on a treadmill going nowhere. 
  • Things change over your lifetime. If you are going to seek help, it is not forever. You don’t have to go to weekly appointments for the next 70 years. Sometimes it is weekly for a while and then it is every two months. It is based on what is going on with your live. It is when you need it, how you need it and you are an active part in deciding what that looks like.
  • After a therapy session there are times when people leave Jenny’s office and feel worse than when they came in. She will often check in with clients before they leave, because she doesn’t want to send them out into the world with an open wound.
  • Is it productive, is it getting you somewhere new or are you raw, sad, hurt and staying there? Therapy is an inherently shaming process, because it requires you to examine things that you don’t want to examine.
  • Your therapist is not judging you. They are not closing the door, calling their friend, and talking about you. There are trained to roll with resistance.
  • It may not be until an hour or a day later, but leave feeling like maybe it got worse but then it got better. Ideally, Jenny wants her clients to leave feeling like they are moving forward every time, but there are going to be days where you feel worse at the end of the hour. As long as that is propelling you forward in the big picture, that is okay. If you are always leaving feeling worse or if you don’t feel like you walk out with any tools or actionable ways to feel better, it wouldn’t be serving you. 
  • Speak up for what you need in the moment. You can say you feel uncomfortable and ask for a different way to talk about the issue. You can only address things if you speak up so you can find a way to make it impactful for you.
  • There is nothing you can say to Jenny that will offend her, and there is no amount of resistance she can’t work with, because of her previous experience with forced therapy in the school. She is not going to fight you and will ask open-ended questions. 
  • Having a mental health person in your life is so important. Physical health, financial health, and mental health are all investments that get returns and reflect in the quality of your life.
  • There are so many things coming at us, it is easy to get lost.
  • There is definitely a difference working with someone virtually versus in person. Jenny wants to have a relationship with somebody first, before anything is done virtually. She wants you to see her body language and she wants to see yours. This way she will know different things that are coming up, if she is on the phone with you.
  • You have to find the preferred mode of communication for you. Some people prefer to have everything written instead of spoken. It is all about creating the system that works for you.
  • Jenny is now fully committed to starting her own practice.
  • While she was putting her business together, she came across a hedge fund that was looking to reduce unconscious bias in their forecasters. She worked with them on a contract, and it was fun, but it was so different than what she was used to. This is why her trainer called her the billions woman.
  • Even in the ideal environment where everything was flexible and there was a lot of trust, she still didn’t want to answer to someone and she wanted to be in charge of how she works, set her own boundaries, and live according to her value system.
  • At this point, she has all of the degrees and has done all the gold star work, but what is it for? Why did she do all of this?
  • Jenny could probably have gotten to where she wants to be by working for someone else, with a lot less debt, but she wants to create a practice where she can decide to take insurance or not, because of what she values in privacy.
  • She wants to hire therapists who represent a wide array of experiences, different races, backgrounds, and religions as well as different practice modalities. Jenny doesn’t want to surround herself only with people who do things and think like her. She wants to create a good structure.
  • Jenny thinks women should be at the forefront of this, and her business name is Forward in Heels. It comes from an old cartoon where Fred Astaire and Ginger Rogers are dancing. Someone said that Fred is great, but Ginger had to do everything he did backwards and in high heels.
  • Jenny wants to flip the idea of us trying to mimic male leadership and say women have their own inherent strengths and ways of doing things. We’ve done it the male way for a long, long time, so let’s see if we can design something from the ground up that is different, instead of trying to fill in the gaps where we can be just like men.
  • Jenny wants to be the therapist she wished she had in her twenties and she wants to be the mentor and the leader that she never saw.
  • It is important to stay true to yourself. 
  • Jenny started with coaching in 2015 and she made a lot of mistakes at first. She blew through her savings and she invested in things that paid dividends, but they didn’t pay right away. She did everything wrong with a mindset that it will still work out. 
  • Part of the reason she took the billions job is because if her business doesn’t work out, she can’t just go out and get a six-figure job, because her field is not high paying.
  • She now is seeing the line on the graph go up and she feels that she is on the right track with her business.
  • Jenny found the Gym, because she went to a Ladies Get Paid Breakfast at the Gym’s old location. She has been networking and it has been a very positive experience for her and her business. It all snowballs. 
  • Jenny did a workshop for her school in 2016 and two and a half years later, she got a phone call about coaching from someone who was there. 
  • Things take time. When the student is ready, the teacher will enter.
  • You can’t force people to be ready. When they are ready, it will be more meaningful.

TAKEAWAY: My biggest takeaway is that physical, mental, and financial health all require some sort of financial investment, but when you invest in these things, you’re truly investing in the greatest possible investment you can make — you! Why would you want to short-change you on living the best life possible?

Random Three Questions

  1. What is a food you hated as a kid and do you hate it now?
  2. What is a show you like to binge watch?
  3. How do you take care of yourself mentally?

Connect with Jenny


Instagram/Twitter/Facebook: Forward In Heels

Workshop: Aligning Your Values with Your Actions (May 1, 2019 at the Financial Gym)

Book: Forward in Heels


If you’d like to get financially naked with my team, and drop any fear or shame you have around money, I hope you’ll reach out to us at the Financial Gym. My trainers have literally seen it all so nothing will surprise us. We don’t care how you got here, we just care about getting you where you want to go.

The great news is that Martinis and Your Money listeners get 15% off Financial Gym services. So if you’re ready to manifest your dreams, like Jenny, in 2019, head over to to get signed up today.

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