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I’ll begin this one with a few critical definitions.
Generational Explorer: a noun, referring to a person who is the first in their family to pursue financial freedom. (Ex. Eva Cheraisi was equally shocked and dejected to find that 6 hours had passed since she first started researching wealth accumulation strategies; even though she was a generational explorer, she’d foolishly assumed a couple of committed hours would suffice in strengthening her expertise.)
Eva Cheraisi: a noun, referring to a girl approaching her 20s at a vigorous, unseemly pace, desperately hoping for a rest stop along the way. (Ex. Eva Cheraisi turns 20 in 10 days, on July 18, and started stress-budgeting on Excel last night.)
I am incredibly proud of my Kenyan heritage. Everyday I wear my Kenyan bracelet on my right wrist, positioning it so that it can easily be seen and recognized by other Kenyans. It’s an easy way of saying, hey Kenyan, I’m Kenyan too, come chat and let me guess your tribe while we’re at it. At age 3, I developed an everlasting affinity for chapati and chai, and at age 19, I abhor every morsel of mursik and exercise caution in the presence of ugali without spinach or stew. My Swahili is remedial at best, but I like to think I can mostly catch the vibe of conversations without translation. I follow long-distance running like a vulture follows street meat, and although I peaked in the 6th grade with my 6 minute mile, I like to think I’m a thoroughly stacked and seasoned Olympian in another dimension.
For all the pride my country I’ve acquired over the years, I am yet to reconcile with the one failure that has tainted my adolescence–lackluster financial literacy. Village-born parents instilled a fierce sense of passion, ambition, and self into me, but the knowledge of Eldoret and Baringo County on optimal financial practices to generate and cultivate wealth only extended halfway. I’ve discovered, since entering university, that dreams and drive are only half of the equation. Navigating an elite institution revealed to me that there is more to wealth than hard work for the rest of the foreseeable future. Dreams and drive eventually dim, and when the light fades and you come from a household that perceives wealth purely through paychecks, you must purchase new light bulbs.
It’s not easy to purchase new light bulbs when the store that sells them has never opened a location in your hometown. In your state. In your country. In your world. In your realm of possibility. It’s not easy to purchase new light bulbs when everyone started the journey to the store years before you knew the store existed. When you are taught that wealth = bank balance, when wealth really = total assets – total liabilities. It’s not easy to purchase new light bulbs when your old ones operated on a scarcity mindset, because money waned and waxed out of any scientifically identifiable orbit.
To be a generational explorer, you must shatter all your light bulbs and start anew. Retrace your steps, figure out exactly where you went off-map, and pinpoint it. Often, you may find that your path veered off before you had control of it at all. Dismantle your necessity for control. Control is an illusory mechanism that generational explorers misread as obtained before comprehension. On this journey, you may encounter control, in its purest form, over curiosity and consumption. To be a generational explorer, you must be wholly committed to consumption–of novel concepts, foreign risks, and improbable uncertainties. You are in control of how far you delve into your exploration–that is your curiosity. Soon you will find that curiosity fuels consumption, and you fuel your curiosity.
Some general tips from an intermediate generational explorer:
- Stay sharp. This journey requires a conscious, calculated effort, and your willingness to employ your wit may propel you from novice to beginner quicker than you think.
- Practice intentionality. You’ll find, sooner or later, that financial freedom is enhanced by intentional habit-building. Unfortunately, we are years behind on habit-formation, but we always thrive with unfavorable odds. Take it easy and then go harder than you ever have. Make habits your bitch.
- Forgive them and yourself. You’ll know who they are.
- Take it slow. Shortcuts are another illusory mechanism. Consume and consume, but if you find your comprehension lacking, go back and retrace those steps again.
- Be a reader. As a reader, I am a sponge. I relentlessly soak in every ounce of information that crosses my eyes, until there is no more surface area for me to store any more. You are a reader. Don’t wait to test that theory out.
- Stop comparing yourself to your peers. I know I just spent half of this white space curating a passionate extended-metaphor to establish how behind we are, but ignore that for a second and take in this metaphor (I promise it’ll be short). When you retrace your steps, take a moment to look around and find fertile ground. Replant your roots here. No matter where you go on this journey, remember that you have your own roots, and they do too. It’s not a race against anyone else but yourself–and your roots if you didn’t plant them right.
- Remember those roots. Who worked day and night so that you were positioned well enough to start this journey in the first place? Who had no investments besides a long-shot on you? Who is counting on you to do it right this time around? Who will cheer you on when you get off-map again, and steer you right back?
Time to get sappy. I know, I’m sorry.
Being a generational explorer means confronting the limitations and gaps in knowledge handed down through generations. It requires a willingness to shatter old paradigms and illuminate new paths, even when the way is unclear. It means embracing the role of a pioneer, with all the uncertainties and challenges that accompany it, and doing so with grace.
Grace, in this context, is the acceptance of our beginnings and the acknowledgment of our growth. It is forgiving ourselves for the times we’ve stumbled, understanding that every step back is an opportunity to recalibrate and forge ahead with renewed clarity. It is the gentle reminder that, though the journey is uniquely ours, we are never truly alone. We carry with us the hopes and sacrifices of those who came before us, and we pave the way for those who will follow.
As we navigate the complexities of personal finance, let us remain curious and committed. Let our consumption of knowledge fuel our curiosity, and let our curiosity drive us to greater heights. Let us stay sharp, intentional, and forgiving, ever mindful of the roots that anchor us and the desire for new light bulbs that propels us forward.
To be a generational explorer is to embark on a voyage of self-discovery and transformation. It is to approach each challenge with a sense of purpose and a spirit of reclamation. And as we continue to chart this course, may we do so with the grace that honors our past, enriches our present, and lights the way for our future.
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Extra extra! Read all about it! My 2024 summer song that reflects the spirit of overall freedom I am chasing and cherishing this year:


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