I hired a 'trainer' to get my finances in shape — and this is what I learned

A "Financially Naked" session with a finance trainer taught me some hard-learned lessons about saving money, investing and debt.
US 1 dollar bills ascending diagonally from stack
Many of us avoid conversations about money — but laying out a financial blueprint can help you take control of your finances.PM Images / Getty Images
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By Jen Glantz

Anyone who knows me knows that I'm always up for talking about the personal and intimate details of my life. I've been sharing them to millions of strangers, via the wonderful world wide web, through blogging and podcasting, for the last ten years.

I'm open about my SAT score (I scored a 950 my first time), my credit score (it lingers around 700), and even how many first dates I went on in February 2016 (that would be 14) in hopes of meeting my soulmate (spoiler alert: I did).

But there's one topic, that if brought up at the dinner table or in an email will stop me dead in my tracks.

That topic is money.

More specifically, personal finances. Ask me how much money I make, how much debt I have, or what my savings account looks like and I will practically spit the water out of my mouth.

It turns out I'm not alone. According to a recent survey from Aspiration, a California-based financial services firm, about one in five Americans don’t tell anyone how much money they make, including their spouses or partners. Aspiration found that only 60 percent of women and 52 percent of men share their salaries with their significant others.

But recently, I did just that. I sat down with my boyfriend of two years and disclosed all my financial details to him, from my savings and checking accounts to my credit card statements. Immediately he eyeballed a huge mistake. The bank that held all the money to my name (AKA my savings account) was only giving me .01% interest every year. His bank was giving him 2.2% interest. In a matter of seconds I found I had been making a very expensive mistake for years.

Since my boyfriend's background isn't in finance (and since it can be hard to listen to a person that you love dearly rip apart your financial state without getting too defensive or frustrated), I turned to Google, typing in: "Finance help NYC that treats you like a therapist".

This is how I first heard of a place called The Financial Gym, which according to their website is a group of financial trainers looking to put you in control of your finances, one step at a time. (Financial trainers aren't certified financial planners, but trained by the company to help you get your finances in shape). My initial thought was that this place combined the two things I rolled my eyes at: going to the gym and dealing with finances. But I decided to give it a shot, especially because I was nearing 30-years-old and was eager to leave my money mistakes in my twenties (along with the cringe-worthy first dates and bad haircuts).

What happens when you work with a "financial trainer"

I booked myself what they call a "Financially Naked" session with a trainer who would compile a comprehensive financial report and help me establish money goals. All of this would be done in-person over the course of one hour, with a follow-up session a few weeks later. This all came as a part of a monthly membership, which is $85/month for one in-person meeting, an on-call financial adviser, and a financial fitness plan suited to my life goals. (For couples, monthly rates start at $145, and for students, it's $35 a month.)

Okay, I'll be honest. The idea of sitting across from a stranger — even one who was qualified to give me financial advice — and exposing my money mistakes (and paying for it nonetheless!) was so terrifying that I canceled this appointment and rescheduled it four times before I finally showed up at the office.

I was greeted by my financial trainer, Georgina, and I admitted how nervous I was to disclose my financial state. She reassured me I wasn't alone. "Most people never tell people about their finances," she said. "Even if it's good." She went on to explain that we’re okay telling friends that we’re on a diet and ditching carbs, but why aren’t we okay saying we’re on a financial diet and want to go somewhere inexpensive?

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We’re okay telling friends that we’re on a diet and ditching carbs, but why aren’t we okay saying we’re on a financial diet and want to go somewhere inexpensive?

I hesitantly unveiled the documents and information I was asked to bring: my monthly expenses, bank account and credit card balances, IRA/401K statement and/or brokerage account, credit score, and goals for the year and the future. That's when she pulled out a questionnaire and I started getting financially naked. We went through my money history and ended with a question I had never been asked before.

“What’s your sacred cow?”

I learned that is an item that you must-have every month. For some, it might be getting their nails done or eating meals out once a week. My answer? Taxi cabs to and from the airport. Since I travel a lot, having to go to the airport at 3 a.m. just isn’t something I want to do via subway or train and paying the money for a taxi is my non-negotiable spending item every month.

We laughed, I cried, Georgina took notes and did every comforting thing a therapist would do, short of saying, "Tell me how that made you feel". When the session was over, she had my entire financial blueprint on a piece of paper and I was hugging her as one would a good friend. That second session I was initially hesitant about was already on my calendar for two weeks later.

What I learned from getting “Financially Naked”

That's when the fun started. I met Georgina again late on a Saturday afternoon, and in her hands was a folder filled with a detailed report on my financial mistakes, goals and future plans.

The report is 18 pages long and Georgina walked me through every single word on the report, explaining things to me and asking questions. Here are the three biggest financial takeaways that changed my personal money game:

1. Make an emergency fund ASAP

As a self-employed business owner and freelancer, one of the things that I always had in the back of my mind, but never acted on, was having a game plan in case something happened to my health or work status (clients letting me go or no new projects coming in). Georgina recommended starting an emergency fund ASAP.

“Typically, we instruct clients to save between three and six months of expenses as their emergency fund,” Georgina wrote in the report. “Since you are self-employed, you should target two additional months to be extra secure.”

Georgina recommended putting this in a separate savings account and going forward allocating at least 20 percent of my gross income each month to this account.

2. Consider investing a percentage of saved cash

One conversation that made me itch with nerves was over my retirement plans. Other than having a SEP IRA, Georgina recommended considering investing to meet other goals, both now and in the future.

“I recommend you start to think about what you might like to invest for,” Georgina wrote. “Your asset allocation will vary, depending on the time frame for using the money.”

Her report also detailed the breakdown of stocks and bonds based on my investment goals. (For me, my short-term allocation was 60 percent stocks and 40 percent bonds).

I knew that before I began investing, I needed more education. Georgina pointed me to a handful of books and podcasts to listen to. While this was something Georgina put in my "game plan" for immediate consideration, it was something I decided to mentally file for later this year, only after I've done my research to make sure I'm investing smart and doing it at a place that doesn't swarm me with hidden fees.

My immediate takeaway, though, was to increase my monthly contribution to my SEP IRA, which Georgina recommended I do just based on how much I have in savings and how much I'm making every month, and to consider putting money into investments, which I promised I'd do sometime in Q3 after conducting more research.

3. Play the points game

Since I travel a lot, for both work and fun, and have a good credit score, Georgina recommended that I pay particular attention to earning rewards for travel and consider if I was maximizing the potential benefits.

One immediate takeaway was to look over my credit cards and assess my miles. When doing that, I realized I had a pool of travel miles that could cover a few upcoming flights later this year. The advice also made me start a conversation with my landlord to see if I could pay my rent via credit card (the answer was yes), so that I could gain even more miles a month on the card for future travel. This simple change wasn't only enough to fund more travel adventures in the future, but could actually save me money on travel I already had on the calendar.

Georgina also noted that the biggest benefit of these cards comes from the sign-up offers when you open them, so I made a mental note to follow this rule before any big life event where I’ll have to make expensive purchases, like moving to a new apartment and finding myself in need of furniture or planning a future wedding. During these types of major life events, it may pay off to open a new card and capitalize on the generous sign up bonuses that come with hitting the spending threshold over the first couple of months.

When the session was over, my head was pulsing and my wallet was smiling. I took the report and held it close, realizing the power of those pages of personalized money suggestions. Would I follow them all? Yes and no. I told myself I’d start slow. I set a 2019 goal of implementing three pages of the report each month into my financial habits.

Just like a personal trainer whips you into shape for bikini season, my time with a financial trainer kicked my butt into finally getting smarter about my finances. And I must say, stripping down to my metaphorical underwear has left me feeling more outfitted to take control of my financial future than ever before.

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