It’s time! Our kids are 12, 10 and 7. Our employers know, the kids agreed, and we have hit all the benchmarks we agreed to.
- A gap year, career break, mini-retirement is a period of time when you stop doing traditional employment and schooling to focus on life.
- Our gap year may or may not be a year. We are taking an extended period of time to travel, adventure and explore our interests together.
- We are not trust fund babies or irresponsible. We have been planning with this goal in mind for several years.
- While we have the core concepts and ideas of what the year might look like, we also are designing it to be flexible. To stay longer if desired or get going if things aren’t clicking.
One of the hardest parts over the past few years is finding a guide on how to leave a job you love? There isn’t one so I thought I’d lead off by creating one and also share what led to this decision.
At age 36 I accepted my dream job. For the past 6 years I’ve had the honor to lead a private family foundation in an executive leadership role to guide grantmaking (giving away nearly $5M each year) , facilitate strategy with community leaders, to see the change in the trajectory of people’s lives, while also personally growing and developing in a way that allowed me to optimized business operations and back office systems to minimize pain points and mitigate risks behind the scenes. I had the personal and professional autonomy and trust of the board members to move strategy forward. I interacted with many nonprofit leaders – having real conversations and exploring meaningful opportunities. I developed a strong relationship with my boss, having one of the best mentors of my life. I had great relationships with peers who also led funding organizations – both in the same community, but also at corporate and national levels. I was well compensated, my ideas were received with gratitude and a desire to improve. Sounds like a dream job, eh? It is.
The decision to resign and take a gap year was not made lightly. As I considered all the options and factors over the last 12 months, I could not find a single example of someone who willingly left a job they loved. Almost every scenario someone was fired or they left a toxic work environment behind. That wasn’t my story, which is why this decision does not seem rational – even to me at times. It’s also why I feel compelled to share how I came to this decision and the steps I took to test various options.
Why am I leaving a job I love? The simple answer is because my kids are 12, 10 and 7 and if ever there was a “right time” to take a gap year and explore the world, this is it. This is an extremely personal decision and looking at each of the factors with your own lens and engaging in conversations with your partner/spouse/kids has been critical throughout this journey. I will share our journey and attempt to answer both the tactical and strategic approach we have taken to get here. I should also mention that I go into much more detail on how we got here in my book (Beyond Normal: A Field Guide to Embrace Adventure, Explore the WIlderness, and Design and Extraordinary Life with Kids).
These are the top 10 FAQ related to this decision
1. What’s the real reason you are leaving?
2. Why a gap year, why not a sabbatical?
3. Couldn’t you just work part-time?
4. What will you do for your kids’ schooling? Won’t this impact your kids education?
5. What about your relationships with friends and family?
6. What about health insurance?
7. What are you going to do? Where are you going? What will atypical day look like?
8. Aren’t you nervous? (inflation, opportunity cost)
9. What has been the hardest part?
10. How can you afford to do this?
Both my husband and I came from working class families and the only way to get ahead was to work more and work hard. Learning about Financial Independence was less about following a formula, and more about how might we look at money differently? What do we actually spend our money on? How does that feel? What do we want in life and is our spending aligned with our values? For example, I really love hanging out with friends BUT I don’t love happy hours. I’d much rather sit around a campfire than in a bar. I’d much rather be actively hiking and exploring than sitting in a spa. I’d prefer the time we spend together as a family doing something rather than watching something. I designed a process I call the Joy Audit (detailed in my book) that helped to define what does joy look like for each member of the family and what resources (time/money) were required for highly rated joyful experiences. The short answer was less than you think.
There are really two answers to this question – Math and Psychology. The math is pretty direct. Your income – expenses = the gap. The goal is to grow the gap, then use tools to reduce the psychological impact. I am not a naturally gifted budget follower. I’m not a natural saver. I am thrifty, creative and always looking for ways to optimize for value but things like tracking our spending or following a budget are overwhelming. Which is why learning about tools that could help me were important.
Psychologically I have learned that we aren’t “normal” meaning that we really try to minimize the stuff that clutters our life. I call those things anchors, often expensive things that offer a dopamine hit, but in 3-12 months later have very little value.
From the technical perspective our life as a family of 5 costs between $75,000-$90,000 a year. We increased our savings each year to eventually live off my salary and save my husbands. While this is not financial advice, I appreciate learning how other are using these tools so here is how we use each of those financial tools and why:
401k/403B: These are long term retirement funds. They reduce our taxable income now and can be a source of income at age 59 ½. We use these as our Coast FI funds. Coast FI determines the amount we need to reach which we then can stop contributing and allow that amount to compound over time. We will have what we need in retirement allowing us to back off our savings rate. We are well past our Coast FI number in those funds
457: This is a deferred compensation fund. When you sever employment this can be used without penalty to cover living expenses. We saved a year’s worth of living expenses with the intention of using it for living expenses once we were no longer employed.
Roth IRA: This is post-tax savings that grows through investments and can be withdrawn tax-free. Before age 59 ½ you can withdraw the contributions without penalty. Children can have a Roth IRA if they are receiving income. This will be our back-up emergency fund
Taxable Brokerage: This is our “savings” investment fund, meaning we automatically contribute post-tax money to this account each month and invest it so we have access to cash whenever we need it. This is the fund we will use first for our gap year expenses.
Savings account: Is a place we put money that we don’t want to spend. This is purely a psychology tool for us. If the money isn’t in our checking accounts we can’t spend it. We generally keep a small amount of money in this account as a safety net from month to month.
HSA: Health Savings Account is a triple win. We put put pre-tax money into an investment account. The money grows tax free and can be used tax-free to cover health care expenses forever. We currently cash flow a majority of our health care expenses and save the receipts to be reimbursed at a later date.
Using these financial tools we have considered very carefully what we need and tested the numbers over several periods of time That being said, we are still considering project-based work which leads into the next question.
9. What has been the hardest part?
Emotionally I am invested in this work. I don’t think I’m done yet. I have more to contribute to this space. Both my husband and I are very honest in saying we’re coming back at some point and we have a desire to stay connected to the work. This might be project-based contract or consulting work, it might mean part-time remote work once we are one our way. As we have done the financial modeling on our life we are not requiring income, yet neither my husband or I are the type of people who sit around.
8. Aren’t you nervous?
There is this thing called inflation and the gap could be an opportunity cost in our resume. We have been following these things, and yet we also know ourselves enough to know that we have tested various elements of this life. Hence the range in costs, and the back up funds available. However there is also considerable transition happening not just in my life and work, but in the life and school of three kids, my husband and I. Some days I take that book of anxiety off the shelf and just spend some time allowing myself to feel that, and yet I have been in much worse scenarios. I take a deep breath, ground myself and put that book back on the shelf. It will be there waiting for me whenever I need it, but lingering with fear and anxiety doesn’t help.
I actually share several practices and tools I use to keep these big feelings in line. Mindfulness, fear-setting, and manifesting are really important to me. I guess to answer the question – are you nervous, I would respond, I am human. I have a variety of feelings on any given day, the days have been on a positive trajectory and sharing the new publicly has actually given me more confidence and encouragement than I expected.
7. What are you going to do? Where are you going? What will atypical day look like?
LOL. This is probably the most loaded question. I think the biggest assumption is that we will travel. Yes, that is true- we will travel during all the times we couldn’t with the traditional school schedule AND we’ll come home too. The way we are approaching this time has less to do with destinations and more to do with people we want to see and connect with that just doesn’t seem to happen. Relatives and friends whom we’d like to connect deeper with, linger longer, learn more about. Our current life still feels busy and we want the opportunity to not HAVE TO get back for something. We are very aware the kids will want to hang out with other kids. We do plan to spend the majority of our time in our RV across the country. I am hoping to even host a few Ordinary Sherpa meet-ups or maybe try hosting a fun community-based family friendly adventure or retreat if it works. We do see our RV as a vacation home on wheels, but we aren’t opposed to continuing to travel hack or finding some cheap flights on a Tuesday. The intention remains: to inspire families to connect through simple and authentic adventure experiences.
To give you a sense of this I will share what we did this weekend that we all agreed was an ideal day for a gap year. We took the RV for the weekend to our cousin’s house, parked in the driveway. The first day my husband helped them with a few projects (unplanned minor thing- life with a handyman), the kids played and ran around the yard, later all the guys took their boat out fishing fishing. That night we had a campfire and made our new favorite campfire snack to share. The second day we went to the farmers market, walked through a story book garden trail, had late lunch at a brewery and hiked to a waterfall, grabbed ice cream and we head to bed.
I can’t stress enough the foundation of creating simple adventures in your own backyard has been the building block for this entire lifestyle. We find we are able to travel anywhere and have so much fun doing the simple things. This weekend we parked the RV and the kids were genuinely excited to be together and figure out what they might try in the new space. There was a beach, a pump track and desire to watch an outdoor movie. The majority of this lifestyle doesn’t cost much, if we travel slower we can also maintain our gas budget a bit better. I know some are saying, but inflation – we traveled 5,000 miles this summer at the peak of gas prices on purpose so that we could experience what this felt like. We adjusted and figured it out and are moving forward.
6. What about health insurance?
This will be an entire episode because there are so many variables at play and options to consider. One factor to share is that we met our deductible for in-network and out-of-network on January 1st 2022 with my daughter’s bike accident. Therefore we are sticking with COBRA on our existing insurance plan through the end of the year. COBRA is an option for 18 months after separation, and in all fairness it’s not nearly as expensive as I thought it was going to be. Once we are on the road there are some other considerations and I want to walk through many more details and give the topic the depth it deserves.
5. What about relationships with friends and family?
As I stated above we are very open to what this looks like, but connection is a huge factor in how we are designing this experience. We are determining where to go based on the people we want to see. We will invite others to join us or meet up if their schedule allows, we’ll be home for critical holidays and quite frankly whenever we feel like coming home. For example, we have been camping with a core group of friends every memorial day weekend since 2007. We’ll be coming home for that experience. Hunting is a large part of my family lifestyle so I can also assure you we will be home for several weeks during the hunting season. I have a suspicion that our experience will strengthen relationships.
4. What will you do for the kids schooling? Won’t this impact their overall progress?
My husband and I are certified teachers which helps, but the truth is we have been experimenting with various forms of homeschooling on the the road during our last 3 years (once we had an idea that this was a goal). Our kids will attend public school this fall and then we will switch to homeschool when the time is right. Thus far, the interest-led learning model, a weekly checklist for structure, and some additional add on experiences as we go have been really nourishing for our kids educational growth. If you want to look at educational theory, the students who receive hands-on experience-based learning outperform their peers 3:1 on tests. I actually care less and less about the tests, and more and more about my children’s wellbeing. Much like my husband and I, we aren’t leaving traditional work to sit on a beach all day. We are leaving traditional schooling behind to foster hands-on experiential learning experiences. I interviewed Jenna of the Rogue Learner in episode 056 regarding project-based learning which might be helpful to understand the type of schooling we are embarking on.
3. Couldn’t you just work part-time?
I have been in conversation with my boss for over 6 months. This was an option on the table and I tested it a couple of times to see. Even as we restructured the organization and added staff, being in a leadership role there is still question if part-time is feasible. I tested it a few weeks throughout the year. Ultimately I decided that in order that in order to be an authentic leadership doing place-based work, meaning the foundation I lead is deeply connected to the needs of the community and helping to drive change, it didn’t feel authentic to do that a few days of week while also living out my personal brand of family adventures around the country.
2. What about a sabbatical?
We explored this too. In speaking with my board it was reasonable to consider 6 weeks, and I decided that wasn’t enough time. That was simply an extended vacation and knowing how it feels to come off a vacation, I would already have those back to work feelings just as we were hitting our stride. While I’m at it I will say we also discussed and interim CEO and different staffing models, but at the end of the day I didn’t think that was fair to the organization or to the person who was hired to fill the space I was leaving temporarily. It came back to authentic leadership.
1. How do you leave a job you love?
This is the question that I had the hardest time finding the answer to and why I felt compelled to record this episode. It comes down to WHY am I leaving. The answers are:
A. Because my kids are 12, 10, and 7. If I don’t do this now I will always wonder. “The only things you regret in life are the risks you didn’t take (Grumpy Old Men).” My kids will be in a different stage in 5 years. My parents are nearing their 70’s, their health and needs might look different in 5 years, My body and health might be in a different place in a few years. I am not running away from anything, the pull of what I am leaning towards is stronger. I’m not burned out either. I recently read a research study on burned out and there were 3 signs: Do you have personal and professional autonomy? (Yes) Do you feel like you belong? (Yes) Do you feel like your contributions matter? (Yes) I failed the burnout quiz LOL. In truth it’s not the leadership, or the culture, or the work. I am leaving the Work I Love to experience a Life I Love.
B. This is an amazing opportunity…for someone else. This is an amazing job and I am grateful for all that I have accomplished and experienced. Which is why it is important that I leave on top and make this the best organization for someone else to lead. It was fascinating the week my news went public, my brain shifted to “what needs to be done in the organization to be in the best place possible.” By seeing the organization without me in the future, I was able to look at the work with an objective lens and not with an emotional attachment to what I wanted to do.
C. Leave the door open: I have more to contribute. I am not looking for another job. I can consider ways to support the work in a different ways. There are projects at work that I would’ve loved to see through, maybe I still can support that work in a different way. Maybe I will have the time and energy to create a solution to a problem I faced as the Executive that can help another Foundation leader. Some of you have already asked: Does that mean more Ordinary Sherpa? That is not necessarily the plan – I want to be really careful not to turn Ordinary Sherpa into a job, but I am excited to give it more of my mental capacity and refine the systems and content that got us here.
We are still several months out from our actual gap year. Part of leaving a job you love is also wanting to give them the space to do what is best for the organization. I now have the top 10 list of things that I want to get done at work, and the time to figure things out and reach out to friends and family about this upcoming experience is still coming.