There will be a point in your FI journey when a stable salary will become less important to you. You’ve built up your savings and investments to a place where you are comfortable. The freedom and flexibility over your time are more valuable than that regular paycheck.

The thought of leaving your job has you nervous though. Even after running the numbers and knowing you have enough, there are still a lot of emotions tied up in financial insecurity. “Do I really have enough? Maybe I should work for one more year.” On top of that, maybe you enjoy your job, don’t want to leave your team down a member during a busy period of work, or unsure what life will feel like without a regular 9-to-5 job.

Setting all of that aside, deep down you know it is the right thing to do, you just can’t seem to pull the trigger. That is why I wanted to chat with my friends Tess Waresmith and Nicole Franklin. Both recently left their careers to pursue something else.

If you listened to episode 138, you know Tess is a financial educator and money coach for women. Nicole Franklin and her husband Tyler are the creators behind the blog, Not Your Ordinary Plan, where they document their journey traveling the world while coasting to FI.

In this episode, both Tess and Nicole share a ton of practical knowledge such as a checklist to prepare for your leave, how to tell your employer you’re quitting, and what to do about that pesky medical insurance. We also get into the mindset side of things such as how to feel confident this is the right decision and embrace the serendipity of a job-free life.

If quitting is something you’ve been working towards, this is the episode for you. I hope you enjoy my conversation with world travelers and early retirees…Tess Waresmith and Nicole Franklin.

Key Takeaways:

• How to know when it is time to leave your corporate job?
• Understanding money dysmorphia
• Test-driving retirement
• What to do before you tell your employer?
• How to let your employer know you’re quitting
• Embracing whitespace and serendipity of a job-free life

Mentions:

Die With Zero: Getting All You Can from Your Money and Your Life

Taking Stock: A Hospice Doctor's Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life

More of Tess & Nicole:

Instagram: @wealthwithtess and @notyourordinaryplan_

Tess’s Free Course: https://www.wealthwithtess.com/fi

Nicole’s blog: https://notyourordinaryplan.com/start-here/

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

I love FI because it allows me to break the rules and live outside the norm. Like, no one has time for 40 years of traditional employment. But little did I realize I left one set of rules only to get caught up in another - the rules of personal finance.

For example, let's look at one popular idea, “spend less than you earn and invest the difference.” My friend Jeremy Schneider says this all the time and for the most part, he’s right. This is a great principle and one of the pillars of building wealth. But where we go wrong is when we get too fixated on a rule and let it box us in. Do we have to spend less than we earn…every year? No, we realize that is a silly idea. If you want to plan a year of travel, take off time to raise a newborn, or work on launching a business, that might be a year you spend more than you make…and that’s okay.

I’m not saying Jeremy hasn’t had a year where he’s spent more than he’s earned. Knowing him, I’m guessing he’s had a couple but sometimes these general guidelines create a limited mindset. Another example is the 4% rule. This one boxed me in for years making me think I needed to reach my FIRE number before I could retire.

I’ve been rethinking that a lot recently and one person who has impacted me is Diania Merriam. Through her 20s and early 30s, Diania worked in sales. In the midst of one of her peak earning years, she decided to take a 2-month sabbatical to walk 500 miles across northern Spain. A few years later, she quit that job entirely and retired from her corporate career at 33. Diania then founded the EconoMe Conference, a party about money. The conference wasn’t profitable the first few years but Diania didn’t care because she felt like organizing this event was her calling. She is the definition of rewriting the rule book which is why I wanted to have her on the show.

I’m hoping through her story, you identify a personal finance rule that might be limiting your thinking. We get into topics like how to get your employer to say yes to a sabbatical, getting comfortable leaving a high-paying job, right-sizing work, and more.

Key Takeaways:

• How to get your employer to say yes to a sabbatical
• Getting comfortable leaving a high-paying job
• Embracing an abundance mindset
• How to right-size your work
• Finding FI-lexbility

More of Diania:

EconoMe Conference: ​​https://economeconference.com/

Optimal Finance Daily: https://oldpodcast.com/optimal-finance-daily-podcast/

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

While we still have a lot of work to do, I’m really glad we’ve made strides in closing the gender pay gap. Women's increased incomes have led to significant changes in household dynamics. More women are becoming the primary or even sole breadwinner for their family.

This change is great and has led to many positives for both men and women. However, our culture is still caught up in traditional gender roles, especially when it comes to money. Many people expect a man to be the primary breadwinner in a relationship. This leads to awkwardness, confusion and tension.

In today’s episode, we are going to talk about those feelings, especially from the lens of men. There is no better person to have this conversation with then my friend Ed Coambs. Ed is a financial therapist and has over 20 years of experience working with individuals, couples, and families experiencing a wide range of money-related distress.

In this conversation, we dive into topics such as overcoming your internal feelings about contributing less financially, managing money with your partner without feeding resentment, and responding to friends when they joke about the income disparity in your relationship.

A lot of juicy topics, so if you’re ready for it, I hope you enjoy my conversation with firefighter turned certified financial therapist…Ed Coambs.

Key Takeaways:

• What happens when your partner is making more than you
• Handling resentment when one partner makes significantly more money
• Managing your internal emotions when your significant other has the career spot light
• Understanding your money origin story
• Societal messaging about gender norms and money
• Responding to your friends make jokes

More of Ed:

www.healthyloveandmoney.com

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

It’s one of the most hotly debated topics in personal finance…Roth or Traditional?

Some argue that the national debt almost guarantees higher taxes in the future and that you should choose Roth and pay your taxes now. Others argue that flexibility and low-earning retirement years should lead you to choose traditional. And of course, some “professionals” highlight that retirement accounts are a scam and you should be investing in their life insurance product to avoid taxes altogether…for the sake of this conversation, we are ignoring that one.

At the end of the day, we all know the correct answer…it depends. It wouldn’t be a controversial topic if there wasn’t nuance in the decision. Multiple factors make it a personalized decision for everyone.

In today’s episode, we dive deep into many of those factors to help you feel equipped to make this decision for your situation. To help me with this goal, I invited on my friend and CFP Rachael Camp.

Rachael recently appeared on the podcast in episode 143, so if you want to learn more about her story and her thoughts about work optionality, get that episode queued up.

In this conversation, we jump straight into it, debunking bad advice, sharing a rule of thumb to decide if Roth or Traditional is the right option for you, discuss how unique factors such as which state you live in, RMDs, and medical subsidies might impact your decision, and ultimately, a case for why this decision should be revisited every year.

So if you want to get deep into the weeds about Roth vs Traditional, this episode is for you. I hope you enjoy my conversation with the owner of Camp Wealth…Rachael Camp.

Key Takeaways:

• The math behind bad advice
• If taxes are bound to increase, how does that change our decision?
• A Roth or Traditional rule of thumb based on your tax bracket
• Changes in your life that might impact how you should be investing
• How and why to create flexibility in your retirement accounts
• A year-by-year approach to maximize your tax savings

More of Rachael:

YouTube: https://www.youtube.com/@CampWealth/videos

Website: https://www.rachaelcampwealth.com/

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

Over the last couple of years, a key group of companies known as The Magnificent Seven has emerged. This group of high-performing and influential companies includes Alphabet, Amazon, Apple, Meta, Microsoft, NVIDIA, and Tesla. These companies are at the forefront of sectors such as artificial intelligence, electric vehicles, cloud computing, and digital services.

They have also been positively impacting much of the growth in the US stock market. Just last year in 2023, these 7 companies’ stocks grew 73% while the rest of the S&P 500 grew 8%. These companies are routinely showing up in many of the financial headlines and it got me wondering, is the US stock market too reliant on a few large companies?

So I reached out to my friend and fellow CPA Erik Baskin, to see what he thought. He had a ton to say. Of course, as any podcaster would, I asked if he would be up to record a conversation about it.

In this episode, Erik shares his thoughts about The Magnificient Seven’s impact on the stock market. We discuss if this concentration is new. We also explore what changes, if any, you should make to your investments because of this.

Erik and I also had this awesome conversation near the end of the episode about when being a super-saver doesn’t make sense anymore. It really had me rethinking a few things in my life currently.

Let’s get into it. I hope you enjoy my conversation with the Airman turned Financial Advisor…Erik Baskin.

Key Takeaways:

• Has the US market become too reliant on a few large companies?
• Is this kind of concentration new?
• Equal weighted vs market cap
• Impacts of investing only in the S&P 500
• Should we be investing at all-time highs?
• When being a super-saver doesn’t make sense anymore

Mentions:

Morning Star Portfolio X-Ray: https://www.morningstar.com/help-center/user-guide/x-ray-overview

Die with Zero: https://www.amazon.com/Die-Zero-Getting-Your-Money/dp/0358099765

The Gap and The Gain: https://www.amazon.com/Gap-Gain-Achievers-Happiness-Confidence/dp/1401964362

More of Erik:

Website: https://www.baskinfp.com/

BLUF Finance Podcast: https://www.baskinfp.com/podcast

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

Things can get complicated quickly in the world of personal finance. From investing and budgeting to estate planning and insurance, there are multiple ways to accomplish what you need to get done.

Let’s take investing for example. There are different strategies including but not limited to passive index investing, value buying, the 3-fund portfolio, rental real estate, stock picking, target date funds, 70/30 splits…Honestly, I could rattle off a hundred different options which is why I wouldn’t be surprised if you got overwhelmed by all of the choices.

The more experience I get, the more I realize, that simple is usually better. Although the word simple can mean different things to a lot of people, at the heart of the meaning, it means something is easily understood and easily done.

So how can we simplify money? Well, my friend Peter Lazaroff wrote a whole book about the topic called Making Money Simple and he is on the show today to share some of those tips. In particular, we focus on investing and budgeting.

On the investing side, we discuss why Peter chose to invest his personal portfolio into one index fund although he has gained a ton of knowledge managing six billion dollars as the Chief Investment Officer at Plancorp. And if you hate tracking every dollar you spend, we discuss an alternative to traditional budgeting, the reverse budget, which is a simplified way to make sure your spending is aligned with your income.

Key Takeaways:

• What matters whenever it comes to successfully investing
• Why Peter invests in only one mutual fund
• The most important factor in investing
• How to simplify spending by reverse budgeting
• How to enjoy your money as it grows

Mentions:

Making Money Simple (free book): https://peterlazaroff.com/freebook

How Peter Invests Guide: www.HowPeterInvests.com

More of Peter:

The Long-Term Investor Podcast: https://peterlazaroff.com/podcast

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

There are going to be differences. And these differences are what lead to disagreements.

Imagine a scenario where you and your friends are booking an Airbnb for an upcoming trip. The group isn’t progressing, and you can tell by the tone people are getting frustrated. Half of the group wants a cheap option while the other half wants a nice place closer to the city center.

This kind of situation happens all of the time and if you zoom out, you can probably understand both perspectives. Someone might be trying to pay off their credit card debt, or student loans, or saving for an upcoming wedding but wants to go on the trip if it can fit within their budget. Another person might be buried in work and this is one of the few weeks they have gotten to take off and enjoy. Spending an extra couple of hundred dollars is worth it to them if it means the weekend turns from a good time to an unforgettable trip with their friends.

At the end of the day, both people want to spend time with their friends but there is conflict because they have other goals that need to fit into their plans. This is messy.

Layer on the fact that people make different amounts of money and that our upbringing makes us value money differently, you can see why these aren’t always straightforward decisions.

It’s not just friends either. These kinds of situations happen with our partners, family members, roommates, and more.

So how do we discuss money with these important people in our lives? And how do we stand up for ourselves whenever we are being asked to do something we don’t want to do?

Well, that’s why I interviewed Allie Volpe today. Allie is a senior reporter for Vox and recently covered a story on how to fight without ruining a relationship. The headline immediately caught my attention as I think this topic isn’t discussed enough in personal finance.

If you’re pursuing financial independence, you are probably aggressively saving or at least very aware of how you’re spending your money. There will be moments when you’ll have to make a decision and have an awkward conversation about money with someone close to you. Allie is going to be sharing language you can use during these situations, mistakes to avoid, and what to do whenever you just can’t see eye to eye.

Key Takeaways:

• The difference between a good fight and a bad fight
• Mistakes people make in an argument that leave the other side feeling terrible
• Questions to ask to get to the root of what you’re really arguing about
• How to listen and make someone feel heard
• How to get to a compromise
• Ways to handle your emotions whenever you’re getting upset
• What to do if you can’t see eye to eye

More of Allie:

Twitter: https://twitter.com/allieevolpe

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/

Yes, your path to financial independence is going to take work and sacrifice but it shouldn’t be miserable. Financial independence is not worth it if it means being unhappy for decades of your life. There should be lots of moments of fun because life is precious both before and after you reach FI.

So in today’s episode, Jackie Cummings Koski is back on the podcast to discuss five of her secrets for making your FIRE journey fun.

If you missed episode 64, first download it to listen to after this episode, and second, let me share a little about Jackie with you.

At 49 years old, Jackie reached financial independence and retired from “Corporate America.” This was an impressive feat in itself but even more impressive for someone who grew up poor, became a single mom in her 30s, and never had over a $100,000 salary. Jackie created her first net worth statement at 38 years old and went on a tear for the next decade saving and investing to comfortably retire before 50.

Now Jackie spends much of her time as a personal finance educator and recently wrote the book, FIRE for Dummies to help others retire early on their terms.

So if you want to reach financial independence and have some fun along the way, this episode is for you. I hope you enjoy my conversation with the dealer of $2 bills…Jackie Cummings Koski.

Key Takeaways:

• Where to cut expenses but more importantly, where to not
• Smart ways to integrate what you enjoy into your FIRE plans
• Understanding your why behind FIRE
• Where to start in your journey to FI
• Milestones to celebrate
• Why you don’t have to be flawless

More of Jackie:

FIRE for Dummies: https://www.amazon.com/FIRE-Dummies-Business-Personal-Finance/dp/1394235011

Catching Up to FI: https://catchinguptofi.com/financial-independence-podcast/

More of The Struggle is Real:

Find show notes and more at https://www.tsirpodcast.com/

Connect with Justin on LinkedIn: https://www.linkedin.com/in/justinleepeters/