“I don’t know how to do bookkeeping or build a website or ….” Judy said as she contemplated creating a very basic service business based in Southeastern, Connecticut. When I showed her how simple bookkeeping would be for her business and the relatively easy web building platforms that are available, she listened but still had too much fear to begin.
To almost every question she had about future tasks and projects, I told her “you will figure it out.” Judy was certainly bright enough and hard working enough to ensure that she would get what she needed done.
Judy was thoroughly conditioned in the outdated K-12 process.  She felt the need to be formally taught in a classroom setting before she could feel competent. “Where can I take classes in bookkeeping? In web design?…” was her typical solution to proposed challenges.
To be clear, taking such classes might be exactly how “you will figure it out” but usually such classes are not needed because in completing a task for the first time, such as setting up bookkeeping for a simple business, competency is created.
If you have the time and money to take classes in things you can likely figure out on your own, then do so.  If you have the need to take classes because you believe you won’t be able to figure it out, then take a class. The issue is not the form of figuring it out but the mindset of “figuring it out”.Many would-be career changers do not move forward because they think they need to know everything in the present related to future tasks and projects.
After our career counseling session, Judy met with a friend in East Lyme who had a small service business.  Her friend showed her how simple it was to set up a system of bookkeeping.  She also invested in Site-Build-It (not my current recommendation as this was 7 years ago) a simple web-building software that came with excellent guides.  (Total cost $320 but well worth it for Judy).
As to other issues, Judy had been concerned about office space in New London, getting permits to work out of her home in East Lyme, transportation for her clients from Stonington who would need assistance (some of her clients were elderly) and a whole host of issues, Judy had a few increasingly brief virtual career coaching sessions and then, in our last session, said: “I know I’ll have more questions but I’m pretty sure I’ll be able to figure it out.” Success!