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159 | Eventual Millionaire | Jaime Masters

Jamie Masters shares her story of overachieving and burn-out, finding Personal Finance, Business Coaching, and Mentoring.

Jaime’s Story

Jaime is a self-proclaimed classic overachiever. At age 19, she was earning $40,000 per year and bought her first home. At age 22, she was already earning a six-figure income. With that, she was the breadwinner of her family. In fact, she was making around three times as much as her juggler husband.

It was “proving” mode. It was–my parents didn’t have a lot of money…we didn’t even have money for shoes…back when I was eight, my mom told me to marry somebody rich because I wanted to have a lot of money. And I said, “Mom, I’m going to do it myself!” It was very much this “I don’t want to rely on anybody else.” So, therefore, I have to take care of myself no matter what.

Early on, she decided to take care of herself. Her chosen career path, tech, was an effort to make a high income even if she didn’t love the job. She thought that six figures would be the answer to everything she wanted. Once she reached that level, she realized that the money wasn’t making her happy.

What I had set myself up for was a life that I didn’t actually like…It’s a test, right. But the overacheiverness was to prove something that made a life that I didn’t even want for all the people to prove to, that, in the end, didn’t care whether I had a life that was enjoyable or not.

Listen: Struggle: The Psychology Of Poverty With Andrea Motenko


By age 24, she realized she had created a trap for herself. She was miserable, heavier, and didn’t enjoy the life she had created.

Jaime realized that she wanted to stay home with their future kids. However, without her income, it would be extremely difficult to make ends meet.

So she made the choice to set up a better financial future by making to decision to pay down $70,000 in consumer debt. Jaime chose to pay down the debt because she wasn’t sure what else to do. Looking back, she calls this a quarter-life crisis.

According to Jaime, it was a pain in the butt for an overachiever to find out what she wanted to do with her life. It’s rarely a linear path.

Enjoy [not knowing what to do] as much as you can because the amount of opportunities that you can have is absolutely amazing! Right, you could do anything. That is a fun space to be in. Except when you hate being in that space because you don’t have an answer.

Now, she tells people to enjoy that time period in their life because the opportunities that pop up when you aren’t sure what you want to do are endless. The idea of doing anything can be exciting and scary at the same time but embracing it can only help the situation.

If you aren’t sure how to move forward, then start by learning. Read a book. Find a mentor. Expand your zone of awareness to find new possibilities.

Related: Best Financial Independence Books


At the time of this transformative period, Jaime tried out a lot of things. From project management to extra gigs and everything in between. It came down to trying out new things and seeing what she enjoyed.

It’s a long-term chosen path of testing things that work for you. That’s what I suggest for my clients now. The more you start testing and figuring out what really works for you, the more you can find out.

As one of her side hustles, Jaime was coaching a friend. Since she was great at giving advice, her friend recommended that she start coaching for a living. At first, Jaime couldn’t get over the ‘woo woo’ factor of life coaching. But eventually, she came around and found her calling.

Finding A Mentor

After interviewing hundreds of millionaires, Jaime has discovered that millionaires seem to know themselves really well. They are good at knowing what they are good at and know when to ask for help. So, Jaime decided to find a mentor to teach her what she needed to know about coaching.

The first meeting she had with her mentor was a short meeting full of helpful advice. However, he was looking for someone over age 45 to train to take over his business. After the meeting, she sent a thank you card even though it was likely he wouldn’t be able to mentor Jaime. Immediately after receiving her handwritten thank-you note, the mentor reached out to offer an apprentice type relationship. Jaime accepted, even though it required working for him for free for the first six months.

Jaime’s mentor taught her everything she needed to know about the business. They were together every single day working on the business. After two years of working together, she struck out on her own. She had a developed workflow to obtain results for her clients. She even offered a 100% money-back guarantee at first to show clients that she was serious.

Nowadays, most mentors and mentees don’t talk every single day. However, it can still be helpful to talk to someone that is walking the path ahead of you that can give you direct advice. There are many nuances in the labels of coaching, mentors, helpers, and such thing, so be aware of the context and needs.

When you reach out to potential mentors, be respectful of their time. Don’t offer to trade a single project for countless hours of their time. Be respectful and the right mentor will find you.

Building Your Business

If you are building a business, then a business coach might be a great asset. In the following example, Jaime dives into her advice for a contractor bringing in gross revenue of $150,000 per year that wants to grow. Generally, she tries to help clients double their income in the first year. If her client is making less than $150,000.00 then the goals focus on sales and marketing. Over and above, the focus changes to getting a team in place.

Assess Your Team

First, you need to assess the team you have. Talk to your people and grade them. Start by ranking people from A to F. Often, you’ll have to fire someone. It can be hard to make that decision but typically you’ll see an increase in revenue quickly.

Sales And Marketing

Successful sales and marketing are critical to growing your profits. First, extract what is really working. Pull that out and double it to start earning more money. Start with the most successful tactic and continue to work your way down the list.

So what we are trying to do is pull out the pieces that will make the biggest difference on the short-term.

Continue working on improving different aspects of your business. Try diversifying your income and weeding out any issues that pop up. You’ll have to recalibrate your systems as your business continues to grow. Don’t be afraid to make changes along the way.

Time Management

You only have so much time in the day. It is important to realize that. You shouldn’t focus on doing more. Instead, focus on the things that only you can do.

Start this process with a time audit. Jonathan uses Toggl, Jaime recommends a Timeular device. After tracking your time, break down the data. Divide how you spend your time into different categories such as administrative, sales, and more. Go down the list and weed out what you should not be doing. For example, consider passing along any administrative work to your right-hand man. Focus your time on where you add the most value.

Focus on being an effective person that accomplishes your priorities. That should include a balance between your home and work life. Don’t confuse productivity or efficiency with getting actual results. Be clear in the results you are working to achieve, and be willing to take a close-up look at which tasks are busywork, and which ones get the results you are looking for.

Doing Less

Don’t be afraid to build a team you trust and hand off tasks to that team. Find a team that can become autonomous without you. Train them well and move forward. You can stick to the tasks that are your ‘special sauce.’

In the long run, most business owners either want to sell their business or work as little as possible. You need to focus on building something that can run without you as opposed to a ship that will sink without you. Learn to let go piece by piece.

How To Connect

You can connect with Jaime on her website, Eventual Millionaire.

Her book is called Eventual Millionaire.

The Hot Seat

Favorite Blog, Podcast, or Book: The Untethered Soul and The Surrender Experiment

An Inflection Point: Sitting down to add up $70,000 in consumer debt. Plus, being on Yahoo’s homepage is pretty amazing.

Favorite Life Hack: Sending out her laundry.

Biggest Financial Mistake: She bought a brand new car for $19,000. She sold it two months later for a $1,500 loss.

The advice you would give your younger self: She didn’t realize how fixable things are. She was so scared to do things wrong that she didn’t want to try. She would tell her younger self that you can always fix something later.

Bonus! What purchase have you made over the last 12 months that has brought the most value to your life? A waterproof notepad in her shower to capture her shower thoughts. And an eye mask because sleep is so important. Plus Nootropics to help her focus. (And don’t forget the Timeular device.)

Listen to the Friday Roundup of this episode here.

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New to FI? Be sure to check out Episode 100: Welcome To The FI Community!

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