There are tasks or items that seem to be really important due to it's seemingly large impact if not addressed (immediately). But in reality, can be can be easily addressed later with little to no consequences. The only real way to identify them is to learn from direct and indirect experience from other startups.
I'm a great fan of the Eisenhower matrix which is more commonly known as the 2x2 matrix (urgent - important).
I'm sure you've come across it some point in your life. It preaches that all to-do's can be categorized in one of the 4, Urgent & Important, Not Urgent but Important, Urgent but not-important and not important nor urgent. Once categorized you can prioritize more easily. High importance & Urgent items obviously get immediate attention, and Not import nor urgent ones get punted down the road (and mostly likely never get done). Eisenhower says. Do the 'important but not urgent' tasks but delegate the 'urgent but not important' ones. I break down my tasks using this method at the beginning of each week to make sure I'm working on the most important things. Simple but effective.
After using the Eisenhower Matrix for some time I found that I typically had tasks in my 'Important and Urgent' category that fell into one of the following 3 sub categories (1) Tasks or things that move the needle in the company. (scheduling and conducting a a sales call with a customer) (2)things that don't move the needle but if not done it could really hurt your company really bad. (E.g.- Company Incorporation filings)
And last, (3) things that don't move the needle but looks like it could really hurt your company if you don't do them right but they actually are of little to no consequences or they can be corrected later - in some cases with minimum effort. (e.g. getting a stock option plan) So in effect, these tasks had been misclassified as 'important' when they really should been classified as 'Not Important'.
The tricky thing about (2) and (3) is that its really hard to distinguish between the two. Especially, items that require expertise that you do not have(legal, accounting, technical) because, like advice, they are derived threw their lens. "You need to be SOC2 compliant if you want to sell to fortune 500 companies" - SOC2 company founder. "You don't want to use online automated legal services when incorporating your company" - Law Firm .
The only real way to correctly filter out the bad from the good is 'experience'. Direct or indirect. But since getting direct experience tasks time and are costly (at times), the better way is to utilize 'indirect experience' - talk to other startup founders and/or see what other companies have done and recommend.
If Clerky has help thousands of companies incorporate and is recommended by Y Combinator, its probably the right option to use to incorporate if you're living of instant ramen, rather then paying a law firm tens of thousands of dollars.
Take away : know that there are tasks or items that seem to be really important due to it's seemingly large impact if not addressed (immediately). But really, can be easily addressed later with little to no consequences. And the only real way to identify them is to learn from direct and indirect experience from other startups.
Someone pointed out to me that this sounds like Amazon's 'two-way door' decision and 'one-way door' decision framework applied to work prioritization. After reading up on it (here), I agree! Same underlying concept. 'Things that cannot be corrected later should have higher priority / importance then things that can be correct later'.