Have Enough to Retire (Early)? 10 Steps to Make Sure

Will you have enough to money to retire (early or otherwise)? Achieving financial independence requires many key elements to be in place and special consideration if you plan to retire early. You need a plan: what will you do? What will you spend? Where will it come from?

In this episode, Eric and Jason discuss a recent blog post by Fritz @ The Retirement Manifesto where he discusses the “10 Steps to Make Sure You Have Enough Money to Retire”. We cover how we’ve been designing our “dream retirement”, how we track current expenses and project future spend, how Jason is drawing down assets and Eric’s evolving plan to use “the bucket strategy”, and much more.


Show Notes

10 Steps to Make Sure You Have Enough Money to Retire – This is The Retirement Manifesto blog post that inspired our episode. Be sure to visit Fritz’ website for this article, as well as all the associated tools we mentioned in the show. We also highly recommend his three-part series on The Bucket Strategy, which we referred to in the episode.

Social Security is an important aspect to consider in most US retirement income plans. This link will take you to calculators that you can use to estimate your retirement benefits. SSA Tools is another useful site, one in which where you can copy/paste your SSA.gov data and use “…clear interactive visuals that let the user investigate how different choices might affect their overall benefit.” It’s a really good tool for modeling different scenarios.

New Retirement.com – More and more people on Reddit seem to be discussing this comprehensive retirement planning suite. They have a very full-featured free offering as well as a modestly priced paid version (free trial here + $10 off if you choose to extend!) with a host of really nice features, as well as consulting services. There’s a very active Facebook community as well.

Financial Order of Operations (Money Guy Show) – is a really great resource that “outlines the 9 steps anyone can take to build wealth and reach financial abundance.” We recommend downloading a copy and having a look at the associated episodes on their YouTube channel too. This is an essential tool to ensure your personal financial habits are supporting your FIRE goals.

You Need a Budget (YNAB) – By our observation, there is no budgeting tool more widely discussed, nor with a user base so passionate than YNAB. If manual spreadsheets aren’t your thing, or you’ve struggled with budgeting, look no further. YNAB has a free 34-day trial and the subsequent annual fee readily pays for itself. (affiliate link – a free month for each of us if you sign up!)


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Healthcare is my Second Highest Cost in Early Retirement

Health insurance may not be top of mind in early retirement when you’re young and healthy, but it should be. In the US, healthcare costs are a significant line item in our budget. To help us decode what you need to know, we’ve invited a retirement benefits expert to answer our questions through the lens of those seeking financial independence and early retirement.

To protect against astronomical expenses resulting from unexpected medical issues it’s prudent to carry insurance and if you’re retiring before 65 (when Medicare kicks in) you’ll be responsible for covering those costs. What do you need to consider? What ARE the costs involved? What insurance shouldn’t you purchase? Are there other options for coverage? What about long term care insurance? These are just a few of the topics we cover in this hour-long episode.

Our sincere thanks to Amy Manning for sharing her time, knowledge and expertise with us!


Show Notes

In this episode we mentioned a number of useful resources primarily for US residents seeking healthcare that we’d like to share with you. Note that many apply whether you are on a FIRE path or traditional retirement age.

COBRA is an important bridge strategy for health insurance for many people in the US, just as it was for Jason. The linked page is a great starting point and points to a variety of other sources that you will find helpful. Please note that some states have additional information available, and may even have further extension coverage offered beyond the federal requirements. As one tip – the best time to research COBRA is before leaving your employer. Your HR benefits partner or healthcare plan administrator is an ideal starting point to gather more information about your company’s plan and coverage options.

Healthcare.gov is the best starting point when it comes to information about Affordable care Act (ACA or “Obamacare”) plans. In many cases, you will be directed to a state-run plan with its own website, but this is not always the case. Presently, a number of states have federally-run, state-federal partnership, or federally-supported plans. Where there isn’t a state exchange, you’ll see options and apply for coverage directly from healthcare.gov.

ACA plan subsidies are a topic worth a deeper dive than our time allowed in this episode. Many on a FIRE path plan on having incomes well within the limits where cost-reducing subsidies apply. Typically, as long as your household income is below 400% of the Federal Poverty Limit (FPL), these apply. When you investigate ACA coverage options, information will be provided on your eligibility for these based on the income information you supply. Importantly, in 2021 and 2022, provisions of the American Rescue Plan (ARP) legislation made further improvements to eligibility, eliminating so-called “subsidy cliffs”.

Healthcare Sharing Ministries (HSMs) are an option of interest to many. However, neither of us are experts on the topic. We’ve looked into HSMs and decided they weren’t for us, as they’re not bound by the same requirements as true insurance plans. That said, this page seems to be a reasonable starting point for high level information on a number of options available. If you have interest in these plans, be sure to dig deeper. Many user stories are available online via Reddit and other sources. For information on the potential downsides of HSMs, we found this recent John Oliver segment very eye-opening. Caveat emptor, friends.

GoodRx and RxSaver are convenient tools to find out where you can get your prescriptions filled for the lowest cost via coupon discounts. A related tip for diagnostic testing + labwork is that for many insurance companies, it’s easy to use their website to confirm your options for in-network testing. Don’t be surprised by higher bills that come from using labs that are out-of-network! A few minutes of work is well worth it to ensure you’re getting the lowest cost options available to you.

Medicare.gov should be your starting point for researching healthcare coverage options for US retirees once they reach 65 years of age. It’s never too early to understand what this will look like for you even though it may seem far in the future. If you’re new to the topic, easy to digest summary information is available on this page. As you develop your retirement budget, this site will be a useful source of information to estimate those future costs.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

How We Travel: Pre + Post Financial Independence

A seven day vacation or 5 weeks of travel – which would you prefer? When you’re working towards financial independence, vacations are a time to set aside work and everyday chores. But they’re constrained by things you don’t often control: accrued vacation time, work and school schedules, business obligations, and holidays, to name a few. In this episode, Eric and Jason compare notes from their two respective sides of FI and their recent vacations: 7 days for Pre-FI Eric and 5 weeks for Post-FI Jason. See just how different is travel once you reach FI and the constraints have been removed.

For more information on Jason’s five-week trip, including the valuable lessons he and his family learned on their longest trip ever, check out his blog post: https://thenextphaseisnow.com/longest-vacation-of-my-life/


Show Notes

As we mentioned in the episode, one leg of Jason’s travels brought the Two Sides of FI together in the same place for the first time in several years, as he and Lorri visited Eric and Laura in Maine. Along with all the fun times we’d planned (and carried out!) for our few days together, we’d intended to film episodes with our spouses – which we did. Unfortunately, a few technical issues meant that we decided not to use that footage after all. However, we believe the two episodes we recorded later with our spouses (Part 1 and Part 2) turned out even better in terms of the quality of our conversations. If you haven’t seen these shows yet, please check them out. Two times Two Sides of FI is the only way to get the full picture!

Two times Two Sides of FI: Jason, Lorri, Eric and Laura
Dinner time in Maine: (back) Eric + Laura, (front) Lorri + Jason

For a closer look at some of our trip photos, check out these galleries:

Eric’s photos:


Jason’s photos:


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Retired Early and I Hated It : How NOT to FIRE, Part 2 (Post-FI/RE)

Imagine hitting your FI number, retiring early, and discovering you hate it? In this episode we discuss four examples of such an outcome: from quitting the perfect job and regretting it, to feelings of depression and lack of purpose. Some are unable to find motivation without financial incentives, while others realize they haven’t budgeted enough to do things they enjoy in life.

This is part 2 of our How NOT to FI/RE series. For part 1 and the PRE FI/RE examples, be sure to check out that video here: https://youtu.be/Jb438jvebd0


Show Notes

For Jason’s own thoughts, observations, and lessons learned in his first year of early retirement, check out this Two Sides of FI episode, as well as his blog post.

Are you on Reddit? Join us in the Two Sides of FI subreddit if you’d like to continue the conversation.

Full text of Reddit posts from the episode:

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.

How NOT to FIRE – Part 1 (Pre-FI/RE)

How much do you really need to achieve financial independence? We decode the math On the path to financial independence, there are ample opportunities for mistakes and missteps. In today’s episode, we review stories from people who shared their FIRE experiences online in the hopes of educating others. Here we review five of these tales: incurring tragic losses due to trying to beat the market, losing 75% of your portfolio value due to sector investing, regretting aggressively saving at the expense of living your life, and resenting your partner who doesn’t have the same degree of FIRE ambitions as you do.


Show Notes

You can find information on the tools we mention in the episode along with additional information in the Resources section of this site! To navigate to this material at any time, just click the menu button at the top of any page on the site.

Full text of Reddit posts from the episode:

Answering Your Financial Independence Questions

You asked, we answered. Bringing the Two Sides of FI together to discuss changing withdrawal rates, Jason and Eric’s own FI numbers, redefining identity in early retirement, rental real estate, and more.

Want your question featured on an upcoming show? Drop a comment on the video or reach out on our contact page.


Show Notes

Given the diversity of topics and tools discussed in this episode, it was challenging to go into much depth on any one of them. We’ve shared more information below on several of these items so that you can get the full details on each.

  1. Our FIRE numbers: We only briefly touched on this topic in this episode, but we’ve actually done an in-depth two-part series in the past. “So, What’s Your FI Number? Sharing Ours Here” is the first, and addresses the question of how to determine how much you need to achieve financial independence. We decoded the math used to calculate our own FI targets, talked about the different flavors of FIRE, and shared where our numbers fall on the FIRE spectrum. The second part of this series, “Discussing our FI Numbers : Changing our Minds, Talking to Family”, goes a step further. There we talked about how our early FI goals and calculations underestimated today’s needs. We then went beyond the math of financial independence to discuss the psychological aspects, including important conversations we had along the way with family and friends.
  2. Modeling your FI plan’s success: In this episode we showed some examples of modeling using cFIREsim, one of our favorite tools for examining the likelihood of your assets lasting the duration of your retirement timeline. This is a commonly used and highly regarded tol among the FIRE community. Newretirement.com is another great site (with both free and subscription options) that provides similar functionality, while including more in depth planning options. Both can be found on the Tools section of our Resources page.
  3. Modeling rent vs. buy decisions: While this wasn’t a major topic in this show, it is a question that comes up often both pre-FIRE and when thinking about modeling housing costs post-FIRE. It’s easy to model scenarios using the Rent vs. Buy calculator at SmartAsset.com.

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

First Year of “Early Retirement” Lessons Learned

Retiring at 47 is early by any definition. In this episode, Jason reflects on his first year in early retirement after reaching his FI goal in 2020. Not everything went smoothly as you might expect. Learn what’s changed, what’s been better, what’s worse, and – importantly – has it lived up to his expectations? If you’re excited to reach this milestone but still harbor some reservations about crossing into “retirement”, Jason offers a grounded, thoughtful perspective on what to expect and how to prepare for such a life-altering transition.

Be sure to read Jason’s milestone post for additional thoughts and details not covered in the video.


Show Notes

Eric here, checking in with a little behind-the-scenes detail. If you’re a long-time viewer, you’ll have noticed we switched sides in the edit. The reason? I joked with Jason after we finished recording the original episode that his next “skill development task” was to learn Final Cut ProX and cut the episode together. He agreed, not knowing the depth and form my critical feedback would take nor the time and effort making changes would entail! The editing switch was a subtle “tell” that we switched roles. And, although I don’t think this marks a permanent shift in our roles for this project, it did give each of us a better perspective on the skills we bring to the collaboration.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site.

Financially Independent, Live Anywhere? How to Choose (Parts 1 and 2)

Part 1:


Part 2:

Choosing a place to call home once you’ve reached financial independence can be an overwhelming task, given just how large the problem space is. As Eric nears his FI number he asks Jason for help and advice on how to narrow the range of options of where to live. Jason shares how he and Lorri approached where to live in “retirement” before taking the plunge to move their family. Irrespective of your own retirement path, the “Where to Live” process they used can be applied universally to making decisions about relocating to a new area.

Show Notes

Would you like your own FREE “Where to Live” tool just like Jason and Eric used in the episode? Please fill out the form below to request a copy:

NOTE: Two Sides of FI will NOT share or sell your information with 3rd party sites. If you are a new subscriber to Two Sides of FI you will receive several emails, including one to confirm your email address.


Do your future plans include relocation in the US? We found a great web-based tool called Mapping FI that we think you’ll find useful. While not as flexible as the approach used in the video, this tool is great for narrowing your search by cost, climate, and demographics.


For a closer look at Jason + Lorri’s and Eric + Laura’s “Where to Live” sheets, please see the images below.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site. To navigate to this material at any time, just click the menu button at the top of any page on the site.

Lessons Learned in 7 Years Earning Passive Income – A Path to FI (Part 2)

Passive Income Flatlay

Diversifying your sources of income is an important step on the path to financial independence. On average, millionaires have at least seven streams of income. In part 2 of our series on passive income (click here for part 1), Eric shares the lessons learned and mistakes made as he created passive income streams for his architecture practice. In 2020, 90% of his small business revenues came from passive sources, bringing him closer to reaching financial independence. Join us as we explore these topics and more in this second episode in our series about passive income.


Show Notes

For more details on all the sources Eric is employing today to achieve this 90/10 split between passive and active services income, the best source is his website: 30×40 Design Workshop. There you’ll find examples of his current offerings, including courses, digital assets, books, videos and even a few of the physical products he’s experimented with.

Eric’s Current Passive Income Streams:

Video content is at the heart of this passive income strategy. For an introduction to Eric’s YouTube content – made not just for architects – his studio + desk tour is a great choice:

To set the passive income flywheel in motion Eric relies on YouTube’s native function as a search engine and positions the video at the center of a hub-and-spoke approach popular with content marketers. The YouTube video captures search traffic, provides information and builds community. As viewers consume the content, the passive income earning assets are positioned contextually to support the information. In this way, a video can show a process and link out to all the tools necessary to recreate the results shown in the video. Some of the assets are products Eric has created, others are more integrated into the ecosystem, like ads. Each video will earn advertising revenue as it’s watched over and again and will also natively link out to content he’s created on his own site, see his blog for an example. The blog post contains even more helpful details and information as well as embedded affiliate links which earn commissions, and links to products he has on offer. They also crosslink to related video content which, in turn, sets the process in motion once again.

Passive Income-Earning Products:

For those unfamiliar, affiliate marketing is where vendors offer content creators a small commission – generally a small percentage of cart sales – for product referrals. Amazon Associates is one of the largest affiliate programs online and, once the content is created, is one of the most passive forms of income you can create. Joining is easy and direct and they offer commissions of up to 4% of total cart value, making the holidays a particularly lucrative time (see below). The Learn section of 30X40 provides a good introduction to how Eric approaches this key opportunity – one appropriate for all interest areas and content types.

Amazon associates revenue page from Nov/Dec 2020
Eric’s Amazon Associates Dashboard from Nov/Dec 2020

Each piece of content he creates aims first-and-foremost to be helpful and points to resources created to complement the information he’s sharing. From short form video lectures, to digital templates, courses, podcasts, products and everything in-between; he converts the by-products of the active design work he’s doing each day into assets which produce income even when he’s away from the studio. This income is then directed toward hyper-saving for his FI goals.


You can find information on the tools we mention in each episode along with additional information in the Resources section of this site. To navigate to this material at any time, just click the menu button at the top of any page on the site.

Financial Mistakes We Won’t Make Again (Part 2)

We all make mistakes on the path to financial independence. Learn from ours as we chronicle the poor choices, bad habits, and missteps we’ve made on the road to FI. In this episode we talk about big ticket items like cars, student loans, and mortgages. Mistakes made in these areas can certainly have a large impact on your FI journey! Join us as we explore these topics and more in this second episode in a series documenting our financial mistakes and missteps on the path to FIRE.

Part one of this series can be found here.


Show Notes

You can find information on the tools we mention in each episode along with additional information in the Resources section of this site. To navigate to this material at any time, just click the menu button at the top of any page on the site.