Timbuktu and 5 questions to navigate a windfall

Mallika Paulraj
3 min readJul 26, 2020


My most memorable New Year’s Eve ever took place in Timbuktu. One of my best friends from college was stationed in Mali with the Peace Corps. Another friend and I (we were an inseparable trio in our college years), decided to go visit her for the turn of the millennium — December 31, 1999 switching to January 1, 2000.

Where else in Mali would one go to celebrate such an occasion, but Timbuktu — the mythical city of lore. For centuries traders traversed the Sahara to bring North the riches of Africa. Timbuktu was the main trading hub they headed for, with it’s repositories of gold and ivory brought up from the South.

California to Timbuktu was quite a trek. Planes and buses brought us to my friend’s host town, but to reach Timbuktu you went by river or over sand. It took us several days of camping in strange places. Parts of the journey had to be made on camel, then across the Niger in a boat and then finally on foot.

With all the modes of transportation, we had no idea if we would reach on time. Through luck and perseverance, we managed to arrive in Timbuktu just as the sun set on the 20th century.

In those days the city had only sandy lanes and houses made of mud. Just big enough to get completely lost in. With Google Maps and iPhones still just a glint in Silicon Valley’s eye, we had no idea where we were going. There was a loose plan to meet up with some other young Americans but how were we to find them. Tired and feeling lost despite reaching our goal, we wandered the streets for a long time before we found a place for the night.

I have two friends I’ve spoken to recently who finally have some money to invest — windfalls they have worked long and hard for. Like everyone else I’ve spoken to in a similar situation, they are agonising over the decisions they need to make. Much like my friends and I reaching Timbuktu but feeling lost, receiving long sought after cash from a business venture or inheritance, brings with it the problem of “now what?”. Whether it’s a $100,000 or $100 million, it falls on you to carefully weigh your options.

Any wealth manager or advisor worth their salt could come up with a very good strategy on how to invest your money, but I’d like to offer you the following questions to think through as well.

Questions for navigating a windfall

I don’t claim that this is an exhaustive list, but these are the topics I want to write about as we navigate our way through 2020. They’re what I see as missing in the discourse around investing.

1. How much of your wealth do you want to manage yourself, and how much do you want to outsource to others?

2. How much do you want divided between real assets and virtual assets? Real assets include rental properties or gold coins, things you can see and touch, but need looking after. Virtual assets include stocks and bonds, which you can manage while sitting on a beach.

3. What investments do you think will do well in the next 20–30 years? Why do you believe that? Do you just “believe” it or have you done the analysis?

4. Do you have a written checklist to analyse any investment proposal offered you?

5. Have you scheduled time into your busy life to educate yourself about investing?



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Mallika Paulraj

Creator of The Superinvestar Framework | Author of How the Best Invest — Make Confident Decisions Like the Investing Superstars