3 Sabbatical Decisions I Made Right and 3 I Would've Made Differently
Photo by Chris Li on Unsplash
A few weeks ago, I was a guest speaker for three student groups at Big Ten universities. The young people who participated were hungry -- curious about how to navigate their careers, what kind of companies to work with, what finance and FP&A professionals do and the future of the profession. They also wondered how I became a professional speaker, and -- not surprising -- how I took my sabbaticals including the “First Retirement”. They had questions about moving to a big city and how not to regret their first decisions once they graduate.
I shared the trajectory of my life and work over the years and explained how work-life differs now compared to when I first started. I talked about my experience traveling all over the world and how it’s shaped my work and my life. I explained where I think the world is going and how to position effectively with skills, mindset, and platform.
When the students asked those questions about my career path and my time abroad, it brought me back 20 years to when I was in their shoes with the same enthusiasm and curiosity. And yet, the answers I gave were remarkably different now in contrast to when I was their age. As I share with many people who come to me for advice, some (and perhaps much) of what’s important in a person’s early 20s is often far less relevant in their 30s or 40s. And what’s important in a person’s 30s, 40s and beyond may not have enough been a thought decades earlier.
It’s funny how talking to young people can put you back in that mindset of someone just starting out and recalling what seems so important. That urgent need to be out in the real world? The excitement of accepting a first position? The size of a first paycheck...and the disappointment knowing much goes to taxes and social security. Remember all that wonder? Yet now, I can’t help but think back to the classic scene in the movie Billy Madison where Adam Sandler’s much-younger classmate shares his eagerness to grow up. Billy Madison, Adam Sander’s character, responds by squeezing the little boy’s face with two hands: “Don’t you say that. Don’t you EVER say that. Stay here. Stay as long as you can. Cherish it!”
The conversations brought me back to my initial decision to veer from my originally-planned career trajectory and take what seemed at the time to be a significant risks rather than follow a more linear path. Ironically, in my line of work, I always consider risk. I advise companies on how to manage their risk and grow effectively. Were my choices that risky? In some ways they were, but in most ways it was a bigger risk not to veer from the linear path.
When making a sizable decision like moving a business or life in a different direction, I sometimes wonder what I did right, what I did wrong, and what could have been done differently or better? While I routinely self-reflect, it’s not often I get to share those perspectives with students 20 years younger. How could my lessons help them change their mindset for the better? What do I wish I’d known 20 years ago?
Reimagining I were 20 years old again, plotting out my career, and with a eye toward an eventual sabbatical, this is what I shared with the groups about what I think I did right and what I would’ve done differently and changing course and taking sabbaticals:
I took calculated risks throughout my career and I didn’t over-analyze my decisions. Admittedly, it’s easy to say in hindsight -- risks are almost never as significant as we make them up to be in our minds. Every position of employment I’ve ever had, I’ve moved on from without having another one lined up. Risky, maybe, but I looked at each hiatus as a time to re-evaluate with a clear mind what the best next step would be, without the influence or cloudiness of current pressures. Indeed it was a luxury to be able to take weeks or months off, but by saving and networking effectively, I was able to do so with minimal interruption. I could then identify and launch into the next opportunity with clarity and enthusiasm. Each time I took a break, a small voice in my head did wonder: “Should I be concerned about a small gap in my resume? Is this career suicide?” I told these groups of students, and others who ask me almost weekly: “No”.
Doing something different is rarely career-killing at all. In fact, I’d argue the opposite; taking time off and doing something contrarian can often work for you, not against you. While my technical background is deep, so are the backgrounds of many people in my field and while I may be ambitious, so are many people in my field. What others don’t have are the unique experiences I have. This ‘experience’ resume has set me apart, just as others’ experiences have set them apart. In many technical fields, as we grow and progress, far more is expected of us beyond just technical acumen. My experiences outside of the workforce show that I’m willing to think differently, work differently, challenge norms, expand my horizons and be creative. That’s hugely beneficial in any line of work and many clients/employers find that attractive. Some young professionals may be expected to merely fill a job role, but eventually they’ll become leaders.
2. Adopting a non-fixed mindset, open to change, I challenged my own worldview. Upon departure from each tenure of employment, including my First Retirement sabbatical, I traveled abroad. Knowing that travel and new experiences would only be as rewarding as I allowed them to be, I set out with an open mind and virtually no plan. While I had a loose idea of destination cities and countries, I had no schedule of what I would do nor see. And that was the point of it all -- to let experiences happen without pre-ordaining them.
That’s something I would tell anyone setting out on their first journey: let life happen, keep your expectations reasonable, and be open. Few of us are as truly objective as we may think we are and while opening ourselves up may raise levels of discomfort or even anxiety, being open, tolerant, and intentionally vulnerable, makes learning happen quickly and deeply. Through each break, I came to learn more that my life and experiences were unique to me in the U.S., and yet, shared great commonality with others 10,000 miles away. It was fascinating to spend time with Hmong tribespeople in Northern Vietnam and teens in Colombia and note how similar we actually were despite our notable cultural differences.
I encourage being willing to slow down, sit back and observe other humans and the way THEY live without judgement. See, appreciate, and internalize the beauty in these differences and a richer human experience will emerge that no book, show or course could begin to address. I truly felt privileged to be a visitor in different worlds experiencing what came to me, not what I came to see. Everything is a learning experience if we allow it to be. Simply put: Be open-minded, challenge worldviews, learn, and grow. That applies to travel and to work.
3. I invested the right amount of time. In American culture, rarely are we able to get more than 1-2 weeks away from work at a time. When I was abroad during each break, I was often asked where I was from. “The U.S.” I would say. “We almost never see Americans here -- how’d you get so much time off,” they’d inquire. “I had to leave my work.”
In other cultures, such as those in Holland, France, and New Zealand, it’s not uncommon to take a month off from work. In fact, in Germany, much of the country shuts down every August and many Germans traipse around the globe. In Australia and Israel, it’s frowned upon for young people not to take a gap year. “Where did you do your gap year,” is a common question future employers ask since it’s a cultural norm and demonstrates initiative and personal interests.
During my first stint abroad, I went to Japan and the Middle East for 2 months. During my second stint, I went to Costa Rica for 1 month. During the First Retirement, I spent 3 months in South America, then returned to Chicago for 6 months, then set out for Southeast Asia for another 3 months. I was immensely grateful I had set aside this amount of time.
Many Americans are baffled by these strings of time for breaks, thinking that a 5 or 10-day trip is the way to go (and I understand this is the only option for many). But I believe it takes an extended amount of time to really achieve mental clarity and get immersed in a culture (see #2 above). On a 5- or 10-day trip, much time is spent on the first days acclimating, the next few days often cramming in as much as possible, then perhaps the last few days mentally stewing about what awaits back home.
With such a dense burst, it’s difficult to achieve a sense of peace and adventure, which may have been the original motivation for going on the trip in the first place. While I know it’s rare to stay for long periods of time in a single place while traveling abroad, it’s that extended time that allows for greater environmental awareness and less chasing of what we may think we’re supposed to see. As G.K. Chesterton is credited with stating: “The traveler sees what he sees. The tourist sees what he has come to see.” My encouragement is to live slowly, meet people, enjoy new cuisines, and - most importantly - rest the body, mind and soul.
And here’s what I might do differently:
Make a reasonable plan. Wait a minute...didn’t I just say I set out with virtually no plan, aside from countries and/or cities I might visit? Yes. And I credit that for allowing me to stay extremely present and in the moment. I might say this was the most rewarding part of what I did!
But I also know that having little plan did cost me time, energy, and money. I sometimes stayed in some shady places I would not recommend, placed myself in a few dangerous scenarios, and spent significant sums of money due to my resorting to last-minute plans. Because I booked one-way flights (given that I didn’t know what city I’d be returning from), I was monitored by security on several occasions. I had to rely on my faith in locals, the vast majority of whom were wonderful people, though I did encounter some swindlers as well. The good news that came from this spontaneity was that these were amazing adventures that forced me to be resourceful and creative. The not-so-good news is that all these years later, because I had a limited plan, I probably could’ve done it all better.
In the absence of some kind of plan, it often forces us to dedicate our resources to what’s at hand. That’s great for presence but it’s not so great for long-term strategic success. The ramifications for last-minute planning while traveling is merely lost time and money (and perhaps some exposure to dangers), but the ramifications for a lack of planning in work and life could be lost opportunities or a failure to move in the direction of desired work or career. To these groups of students I met with, I encouraged them to have a long-ish term plan. Rather than have a 10-to-20 year plan, which was the encouragement of my counselors and advisors when I was in school, I encouraged the young people to have a 3-year plan or one much shorter in time horizon but long enough to be directionally helpful. Know where you’re wanting to go, but know for certain there will be shocks and changes. Stay open-minded and open to opportunities within those short years even while you have your eye on the future.
If there is anything that 2020 has shown us, it’s that humans and organizations alike are extremely resourceful and resilient. No matter what is thrown at us, we will figure it out as we have for generations. Of course we would never choose to be completely vulnerable and exposed to insecurity, but it’s going to occasionally happen and when it does, we must trust ourselves to innovate and recover. Oftentimes, the resulting resilience will be more robust than it was before the shock.
2. Spend more time thinking about the next chapter. Not so dissimilar from #1 above, it’s important to plan but also set time aside to focus on carrying out that plan. Each of these stints of travel gave me plenty of time to reflect, enjoy peace and pursue inspiring experiences and interests. But I didn’t use that time so effectively to formally execute my next business venture. Thus, it was only when I returned to the U.S. mainland, and not when I was abroad, that I put all my efforts into pursuing business growth.
Looking back, I would acknowledge my shorter-term focus and mindset, geared toward being present, likely played a factor in both: a) my desire not to execute while I was abroad, and b) my desire not pursue other work opportunities while employed at firms. Each time I returned from my travels, I reentered my work through consulting -- part-time work for multiple clients or full-time work for a single client within a set timeframe. The scope of work was always solid and enjoyable, but I wonder what I could have done better had I devoted some of my time off to create a more formal business model while I was on sabbatical. Having such an abundance of time was a luxury and I think I could have been more purposeful about how I would execute my next professional adventure.
Sheryl Sandberg, of Google and Facebook fame, has also encouraged having shorter-term plans, acknowledging that the world is changing so rapidly and so is our career progression. Imaging the next 10 years is helpful but planning for them definitively is unrealistic. Just as there is more of a work-life blend than a work-life balance, I was short-sighted to separate work from leisure. I also could have more effectively executed upon my business plan while still focusing on the present experience. I told the students you can be successful blending your choices, working or exploring during the day and moonlighting at night to position for what might be next.
3. Skip the worry. Admittedly, I did worry about the future. Even though I took calculated risks, I was concerned about the consequences of some of my unconventional decisions. What would my resume look like with gaps? If I’d stayed with my prior firms, would I forgo making Partner? Is this worth it? How would I explain this contrarian approach to work and life to clients or even people who are closest to me (friends, family)?
Many of the students I spoke to asked questions about making choices early in their careers. Several seemed deeply anxious about choosing the wrong job right out of college that could lead them down a life-long path of regret. Some even looked at internships, weighing which internship at 18 years old would position them most effectively 10 years from now. They were so deeply worried about making a mistake. My answers may have surprised them because I highlighted that worry is generally a waste of time.
I explained that they are smart people, with an education that will serve them well throughout their lives. But yet, the education they’re entrenched in will serve as only a slice of the developmental pie they’ll be accumulating throughout their early careers. No decision, such as a first job out of school, no matter how grand that decision may seem at the time, is so pivotal in determining the direction and worth of someone’s life. Few decisions are truly permanent, and the ability to be marketable with career fluidity, is sometimes more important than that first job. As long as learning is taking place and networks are growing, it’s likely a worthy venture.
The mind can fixate on risks and negatives, especially when it’s free to wander. At 20, I was not much different than those students. If I could go back, I’d skip the hours I spent fretting about what I should be doing and the consequences if I made a mistake. In short, I’d own who I was while also recognizing the extent of my resilience and ability to just figure life out when things change -- as we all know they will.
Final Thoughts
Having taken several sabbaticals, and now witnessing the world changing so rapidly because of COVID, I wonder if more people (and Americans in particular) will see them as increasingly more realistic -- not just practical in a logistical sense but as normal within the context of one’s worklife. While I may have been among a minority in my generation to take such a contrarian approach to work and life, these students I met with viewed my sabbaticals not as a luxury but as an integral part of the future lives they envision. Few can imagine working in a career or job for the entirety of their lives. But at the same time, they’ve been educated for a linear career path and conditioned to follow a recipe for success. It makes them nervous.
Life and work aren’t all about following rules and sequential steps, a series of preordained progressions for achieving goals. I don’t suggest all 2o-year-olds, or even those notably older, should take extended sabbaticals and make some of the short-sighted mistakes I’ve made. But I do encourage young people to take calculated risks, set themselves apart from the crowd, and enrich their lives with unique experiences. It’s no longer about having the perfect resume; it’s more about having a rich resume full of academic rigor, vocational accomplishment, and life encounters. That’s not only helpful for their career positioning; it also builds character. If we’re to build better leaders in business and finance, we need to expose young people to unique experiences and risks that teach problem-solving and foster resilience. There is no better way to do that than expose them to a world they have not yet seen.