The Goodbye July Podcast

Hosted by Jessica Tolar

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May 2026

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About the show

Money questions don’t usually show up all at once. They show up in small, everyday moments. Wondering what to do with extra money. Feeling unsure if you’re “doing it right.” Trying to make a decision — and avoiding it longer than you want to. This podcast is a place to think through those moments more clearly. Hosted by Jessica Tolar, each episode offers a steadier, more realistic way to approach your money — without pressure to optimize everything or completely change your life. Because most of the time, it’s not about doing more. It’s about making a few thoughtful decisions that actually fit your life. www.jessicatolar.com

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47 recent

May 6, 2026Episode 467 min

046: How Much Your Tax Return Could Be Worth If You Put It to Work

Wondering what to do with your tax return? Learn how putting it to work — instead of spending it quickly — can quietly improve your long-term financial picture and create more flexibility over time. ***** Rate, Review, and Follow If you’ve been listening and something here has been helpful for you, I’d really appreciate you taking a minute to rate or review the show. It helps more people find it — especially people who are looking for a steadier, more realistic way to think about money. You can scroll to the bottom of the show page, tap the stars, or leave a quick review. And if you haven’t already, go ahead and follow the show so new episodes show up for you when they’re released. ***** Listen on Spotify? You can follow the show there so new episodes show up in your feed.

May 28, 2024Episode 4518 min

045: 4 Strategies to Dodge the Next Company Layoff

Let's confront the looming specter of layoffs head-on. If your anxiety mounts when it comes to layoffs, fear not: we're unveiling 4 savvy strategies to navigate the turbulent waters of corporate restructuring. From setting measurable goals aligned with company objectives to keeping your manager smiling, we've got you covered. Plus, don't miss our bonus tip for securing financial peace of mind in the midst of it all. Let's dive in! SHOWNOTES: jessicatolar.com/045 Rate, Review, and Follow If you’ve been listening and something here has been helpful for you, I’d really appreciate you taking a minute to rate or review the show. It helps more people find it — especially people who are looking for a steadier, more realistic way to think about money. You can scroll to the bottom of the show page, tap the stars, or leave a quick review. And if you haven’t already, go ahead and follow the show so new episodes show up for you when they’re released. ***** Listen on Spotify? You can follow the show there so new episodes show up in your feed.

March 6, 2024Episode 4416 min

044: Why "F*ck The Patriarchy" Won't Work (And A More Effective Approach to Getting What You Want)

When a coworker betrayed me, I learned a valuable lesson. I was a fresh-faced, eager 21-year-old who had just relocated to a new city for work. It was an exciting time, however, before long I started to see storm clouds that threatened to cast a shadow over my otherwise sunny outlook. It felt difficult to gain respect at work, especially with one man in particular. I remember him so clearly - this particular engineer who went behind my back and did something that felt like a slap in the face. It stirred an emotion I’ll never forget, but most importantly, it taught me a valuable lesson… I realized at that moment I had two choices: I could rebel against him, or I could choose a different approach. Join me inside to learn what I did, why, and how you can use the same approach to get what you want. SHOWNOTES: jessicatolar.com/044 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

February 28, 2024Episode 4315 min

043: Flip the Script: 3 New Stats About Women in the Workplace (And How to Use Them for an Edge)

Once a year, global management consulting company McKinsey releases its “Women in the Workplace" report about women in Corporate America. It's full of interesting data on how we’re stacking up when compared to our male counterparts, the struggles we face, and what the companies themselves can do to help. Whether it's learning what you're up against, which promotion will be the hardest, or how the corporate environment overall has changed in the last couple of years, knowledge is POWER... And I believe re-framing 3 statistics from this year's report can actually HELP you gain an edge at work. So, in today's episode, we're zooming in on these 3 stats, why they matter to you, and what you can do to benefit from them. I'll see you inside! SHOWNOTES: jessicatolar.com/043 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

February 20, 2024Episode 4215 min

042: 3 Ways Self-Love Can Make You Richer

Every February, I like to remind you (and myself!) that outside of the love you share with others is the very special and important kind of love you share with the *most* important person in your life... yourself. And, although self-love is important in more ways than I can say, I’d like to discuss a more practical reason self-love is important… Specifically, how self-love shows up in your BANK ACCOUNT (yep, you read that right!). So, if you need a kick in the pants to ensure you remain (or become!) the main character in the story of your life, join me inside to learn 3 ways self-love can make you RICHER! Let's jump in! SHOWNOTES: jessicatolar.com/042 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

February 13, 2024Episode 4123 min

041: Understanding 3 Employer Benefits That Get You Invested (401k, ESPP, and RSUs)

When I was in corporate, I placed a heavy focus on benefits when I was first considering a job, but then I'd get so busy doing the job I'd forget to use, optimize, or even just try to UNDERSTAND all the different benefits I had – especially the confusing acronym ones. Same for you? Well, it wasn’t until I used my benefits package to negotiate a raise *4x the national average* that I realized just how much benefits truly translate into MONEY. And that’s when I got serious about understanding not just some but ALL of my benefits -- and getting strategic. In this episode, we're digging into 3 of the big ones… 3 employer benefits which, if you're *USING*, means you’re already investing (whether you realize it or not!). I'll meet you inside as we de-mystify the 401(k), ESPP, and RSU - and how you can use each to make more money! Let's jump in! SHOWNOTES: jessicatolar.com/041 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

January 31, 2024Episode 4021 min

040: 5 Habits of Highly Successful People

I had the privilege of getting to know the CEO of one of the world’s largest real estate franchises and, in the ~2-year period that we all spent time together, I quietly observed him – it’s amazing what you can learn by simply watching someone who has skills you admire and would like to adopt. Much of what’s included in this episode comes from my observations of this man, whom I came to respect, and it also comes from observing other executives throughout my corporate career, conversations with them, as well as other high-net-worth individuals. For this episode, we’re defining "success" as your ability to reach the goals you’ve set. Whether that’s a certain level of wealth, a title at work, or a type of lifestyle - that’s beside the point. The point is: you have goals. Are you reaching them? Whether you feel good about your ability to hit your goals or not, you’ll benefit from what follows on 5 habits of highly successful people. Let's jump in! SHOWNOTES: jessicatolar.com/040 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

January 23, 2024Episode 3917 min

039: The Anatomy of Your Quarterly Reviews with Your Boss

IMHO, one of the best things you can do to move leaps and bounds closer to a lower-stress life with more freedom is to consistently get pay increases… and invest all of them. If you’re already living comfortably and can work out a process for getting regular pay increases and investing all of them, you’ll be amazed at what becomes possible and the doors that open up for you financially. But first, there’s the matter of securing the raise itself, in a way that’s sustainable and consistent. And one of the most effective ways to do that is through quarterly reviews with your manager. In this episode, we’re talking about just that – The Anatomy of Your Quarterly Reviews with Your Boss. We’ll cover: When to schedule them How to prepare What to cover in the meeting Let’s jump in! SHOWNOTES: jessicatolar.com/039 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

December 27, 2023Episode 3826 min

038: Welcome to Investor Prep School!

Welcome back for Part 5 of our 5-Part Mini-Masterclass on Investing. In Part 1 you learned about 9-steps to get started investing, in Part 2 you heard 5 common mistakes most new investors make and what to do instead, in Part 3 you explored 5 types of investments and which might be best for you, and in Part 4 you saw various investment models ranging from $100 to $1M and everything in between. In this FINAL episode of the mini-masterclass series, I am beyond excited to pull back the curtains and give you a behind-the-scenes look into my program, Investor Prep School! Specifically, we will walk through: Who this program is for so you can quickly decide whether or not you’re a fit What exactly you get, including a step-by-step walkthrough of each module plus bonuses Top FAQs plus information on the risk-free money-back guarantee So excited... let's jump in!! SHOWNOTES: jessicatolar.com/038 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

December 20, 2023Episode 3722 min

037: Investment Models: From $100 to $1M+ and Everything in Between

Welcome back for Part 4 of our 5-Part Mini-Masterclass on Investing. In Part 1 you learned about an A-Z 9-step roadmap to investing, in Part 2 you heard 5 little-known mistakes *most* new investors make and what to do instead, and in Part 3 you learned about 5 different asset classes. In this episode, I am excited to show you that you don’t have to have tens of thousands of dollars to invest every month to see change in your life. Specifically, we will walk through 5 examples of different initial investments, monthly investments, and age at the time of first investment so you can see how compound interest could potentially help your money grow in various scenarios. Let’s do it! SHOWNOTES: jessicatolar.com/037 Rate, Review, and Follow on Apple Podcasts “I love Jess and The Goodbye July Podcast” ← If that sounds like you, please consider rating and reviewing my show! This helps me serve more people (like you!) and support them in organizing, automating, and growing their money so they can build the HELL YES life they deserve. Click here, scroll to the bottom, tap to rate with five stars, and select “Write a Review.” Then be sure to let me know what you loved about the episode! Also, if you haven’t already done so, follow the show. I’m regularly adding episodes to the feed and, if you’re not following, there’s a high chance you’ll miss out. Follow now!

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