Getting Wild In Retirement

Want To Reach FI Sooner? Join more than 18,000 others and get new tips and strategies from Can I Retire Yet? every week. Subscription is free. Unsubscribe anytime:

Cheryl Strayed was recently featured on the Outside podcast. Strayed authored the best selling book, later adapted to a feature film, Wild. The interview celebrated the 10 year anniversary of publishing her book, which was about backpacking the Pacific Crest Trail (PCT).

Backpack and boots

I read the book last year and loved it. I was curious to hear what she’s learned and how her life has changed since Wild was published.

A few key lessons she shared jumped out to me as directly applicable to our own journey to financial independence and early retirement.

Preparing for the Unknown

Prior to hiking the PCT, Strayed had never done a long through-hike. She addressed the most common criticism that she heard after the book was published. She was unprepared to embark on her trip, maybe dangerously so. 

Her responses were telling. “….I did nothing but prepare in the months before my hike, I just made some mistakes.” She later added, “My problem wasn’t….I wasn’t prepared, I was over prepared. I had too much stuff.”

This is portrayed in the book, and subsequent movie based on it, as she describes her backpack. She named the pack “Monster.”  It was an epic effort each time she hoisted this beast of a pack onto her back. Carrying all this weight caused pain and suffering with every step (see video below).

As her hike went on, she learned from her experience. She cut unnecessary weight in her pack. As she lightened her load, her days became more enjoyable.

This is common as we prepare for retirement. The future is full of unknowns….stock market returns, interest rates, inflation, life expectancy, personal health, tax rate changes, viability of programs like Social Security, the Affordable Care Act and Medicare. 

So we keep adding. Work longer to build a larger portfolio. Find more information. Get the right advisor. Buy more insurance. Add more complexity.

Related: Should You Work One More Year?

None of this is to say we shouldn’t prepare. We absolutely should.

Nor am I suggesting that there is not value in the right financial products or services. There may be.

But all of this leads to a second parallel between Strayed’s adventure and our financial journeys.

Overcoming Elitism

Strayed feels her critics’ arguments were often based in elitism and snobbery. These arguments dissuade people from trying hard or scary things. Strayed said, “Most of us learn most of the important things by going and doing them….”

This truth extends far beyond her backpacking adventure. It is absolutely true as we make life decisions, utilizing the financial independence we have worked so hard to achieve.

I experienced this elitism when working with a financial advisor. When I talked about wanting to retire in my 40’s, he would give a subtle eye roll and return the conversation to the fancy financial plan he created. 

My early writing was critical of this advisor and the financial industry generally. I needed to own that I wasted a decade waiting for this “expert” to give me permission.

As I found FIRE bloggers and subsequently became one myself, this elitism from the financial industry became more apparent. Most financial professionals scoff at us. What could anyone possibly learn about finance from engineers, health care professionals, school teachers, etc.?

This isn’t to suggest that there are no true experts and that we shouldn’t learn from them. But pay attention to what someone says rather than what letters follow their name. 

Are they using their knowledge and experience to educate you or to overcomplicate things? Are they more invested in your success or in selling their products and services and protecting their turf? 

In the decade since Wild was published, the internet has given more people permission and knowledge to get into the wilderness. The same can be said of helping a larger number and wider diversity of people using their personal finances to create better lives.

That has been my motivation for writing this blog and creating my book.

What Is THE Best….?

One of the most memorable moments in Wild was portrayed in the opening scene of the movie adaptation. Strayed’s ill fitting boots are killing her feet. She takes them off while taking a break along an exposed section of trail.

While she sits and rests, one boot tumbles over the edge of the cliff. Gone forever. It induces a brief mental breakdown, where in frustration she launches her other boot as well.

In the anniversary interview, Strayed was asked what boots she would recommend for a 1,000 mile journey? She replied, “The boots that feel good on your feet….There is no one way to do anything….We have to find the path that is ours, we have to walk it at our own speed, in our own way. That’s the beautiful adventure of life.”

This is a message frequently conveyed on this blog. Over the years, Darrow and I have shared our personal paths with honesty and transparency. We’ve shared what has worked, as well as challenges.

Over the past few years, I’ve tried to mix in some different perspectives, always taking care to emphasize there is no one “right” way and to avoid dogma.

In one of the earliest posts on this blog, Darrow defined early vs. traditional retirement. In one of my first posts on the site, I discussed redefining retirement.

Since then we’ve shared insights on a number of different paths to help make successful transitions to whatever you determine comes after financial independence. They include:

Choose Your Own Adventure

Take the valuable lessons that Strayed learned backpacking the PCT and writing about it in her memoir Wild. Use them as you navigate this next phase of life.

Take time to understand the unknowables involved in retirement planning. But don’t allow them to overwhelm you and drive you to inaction.

Learn from true experts. But don’t confuse expertise and elitism. Expertise is used to help and educate you. Elitism can be used to trap you in fear and sell you ever more services and products.

Find your own path. It will be different from mine and everyone else reading this. It should be. You are different from me and everyone else reading this.

* * *

Valuable Resources

  • The Best Retirement Calculators can help you perform detailed retirement simulations including modeling withdrawal strategies, federal and state income taxes, healthcare expenses, and more. Can I Retire Yet? partners with two of the best.
  • Free Travel or Cash Back with credit card rewards and sign up bonuses.
  • Monitor Your Investment Portfolio
    • Sign up for a free Empower account to gain access to track your asset allocation, investment performance, individual account balances, net worth, cash flow, and investment expenses.
  • Our Books

* * *

[Chris Mamula used principles of traditional retirement planning, combined with creative lifestyle design, to retire from a career as a physical therapist at age 41. After poor experiences with the financial industry early in his professional life, he educated himself on investing and tax planning. After achieving financial independence, Chris began writing about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. Chris also does financial planning with individuals and couples at Abundo Wealth, a low-cost, advice-only financial planning firm with the mission of making quality financial advice available to populations for whom it was previously inaccessible. Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He has spoken at events including the Bogleheads and the American Institute of Certified Public Accountants annual conferences. Blog inquiries can be sent to Financial planning inquiries can be sent to]

* * *

Disclosure: Can I Retire Yet? has partnered with CardRatings for our coverage of credit card products. Can I Retire Yet? and CardRatings may receive a commission from card issuers. Some or all of the card offers that appear on the website are from advertisers. Compensation may impact on how and where card products appear on the site. The site does not include all card companies or all available card offers. Other links on this site, like the Amazon, NewRetirement, Pralana, and Personal Capital links are also affiliate links. As an affiliate we earn from qualifying purchases. If you click on one of these links and buy from the affiliated company, then we receive some compensation. The income helps to keep this blog going. Affiliate links do not increase your cost, and we only use them for products or services that we're familiar with and that we feel may deliver value to you. By contrast, we have limited control over most of the display ads on this site. Though we do attempt to block objectionable content. Buyer beware.


  1. This really resonates with my Schwab advisor. Quizzed me on technical terms like Modern Portfolio Theory to demonstrate that A DIYer couldn’t possibly manage his own portfolio. Doesn’t provide much advice at our annual reviews, but loves to try and sell me additional products and services.

  2. “I experienced this elitism when working with a financial advisor.”

    I felt this way too in my late 30’s when I started to accumulate some meaningful wealth and considered hiring an advisor. The advisor asked me what my objectives were and I replied “rapid wealth accumulation” which was met with a condescending eyeroll. I proceeded to explain that my growing portfolio consisted of a diverfied but simple set of low cost all stock mutual funds (ETFs weren’t around at the time) including small, mid and large cap domestic and international stocks. I then asked what might be wrong with what I’m doing and what he would do to improve my situation. After much mumbo-jumbo, it sounded like he was simply trying to spin me into higher cost, similar investments. After churning through a few advisors who all basically said the same thing, I dumped the whole idea of hiring one. My very simple investment strategy back then was perfectly fine.

  3. Great article Chris. One of the things that bothers me most about the personal financial planning ecosystem is how so many people, both professionals and clients, equate financial planning with investment management. I’m sure many FP professionals provide sound investment strategies. But many are just trying to sell what they have. And many clients (I know man) think there is some magic sauce that FP’s have that controls the market. Sound FP looks at investments, but also taxes, estates, insurance, benefits, cash flow and much more. A good FP worries about you and your family and wants to see you succeed. If you don’t have that type of planner, find a new one. they are out there. Many of us are comfortable figuring this stuff out on our own, or engaging an expert where needed. For those who aren’t, paying a holistic planner to get you on a sound plan is money well spent. My first article on HumbleDollar addressed this.

  4. Great column and advice. I had similar experiences with a financial planner not providing much value. Your blog posts provides a breath of fresh air and sound information. Thank you.

    The quote above about finding and walking your own path through life sums it up well. In business, I saw many teams/committees waste a lot of time planning only to have chaos ensure once they took an action. They didn’t take time to experiment and learn from their experiences. Instead of trying to implement the entire change at once.

  5. I really needed to read this today as I am one month into my OMY. Thank you for all of the references to reread some of the wonderful archived posts.

  6. I always say there’s a reason they call it “personal” finance. I met once with a FP. He listened, and looked at what I had in place, then told me I didn’t need him. I can’t tell you how much I appreciated his honesty.

    Our path to early retirement worked for us because it was in lockstep with our values every step of the way. Not saying I didn’t make any mistakes, but I learned from them and moved on. As it turns out, a dedication to self education in the fields of finance and investing proved to be one of our biggest assets.

    Good post, Chris, with excellent analogies. Nicely done!

Comments are closed.