I’m trying something new.
I’m offering 1:1 consulting/coaching sessions for my readers, meaning you, and the people who follow me on Instagram and TikTok who want to diversify their income streams using the skills they already have.
I want to understand what people are actually struggling with, so I can work out the most useful way to help. 3 people took me up on the offer, and I’ve already had my first session.
Before the call, I was ready to consult.
I expected to speak to someone who wanted to diversify their income, and needed advice on mapping out options.
Instead, I ended up speaking to someone in the middle of a career transition, going from job A to job B.
She wasn’t interested in diversifying jobs.
I’ve changed her name for privacy, and she knows I’m sharing the story privately.
Let’s call her Claire.
Claire is a self-taught data scientist. She worked her way up through the startup world and eventually became a successful executive at a tech company, where she spent 5 years.
Then, recently, her role disappeared almost overnight when the company went under.
A high salary like she had before (around £180,000 per year)
Flexibility and remote work
More time with her family
Work that aligns with her values (sustainability space)
A new job within 2 years, though she has enough savings to wait longer if necessary
Go back to school for a master’s degree
Accept one of the job offers paying £90,000 a year
Start consulting
Keep searching for a better opportunity
What happens immediately (first-level thinking):
She spends more than 30 hours per week studying
She has less time for family
She earns less money in the short term
What happens immediately (first-level thinking):
She earns an income again
Her bills are covered
She makes less than she ideally wants
She may need to save more aggressively for future goals
What happens immediately (first-level thinking):
She gains flexibility
There is uncertainty about demand
She doesn’t know how much she can earn
What happens immediately (first-level thinking):
She risks losing the offers currently available
She gains more time to find something better
Her savings continue to decrease
Throughout the session, I basically kept asked questions that only she knew answers to.
What I found interesting in my conversation with Claire was that the obvious next step was not necessarily the best next step.
This is where second-level thinking becomes useful.
First-level thinking asks: What solves this problem right now?
Second-level thinking asks: And what happens after that?
Let’s look at this:
Best-case scenario
She receives financial support or a scholarship
She develops valuable new skills
She builds a strong network
Better opportunities become available
She eventually earns the income she wants
Worst-case scenario
She accumulates debt
The skills she learns are not highly valued by employers
The degree does not significantly improve her opportunities
She ends up needing another job search anyway
Can she get a scholarship?
Does the program have strong industry connections?
Are employers actively hiring for those skills?
What salaries do graduates actually achieve?
How long would it realistically take to reach her income goal?
Best-case scenario
She gains experience
She advances within the company
Her salary grows over time
She develops skills that improve future opportunities
Worst-case scenario
She remains underpaid
She dislikes the work
She becomes stuck in a role she doesn’t enjoy
Her situation is not much different from where she is today
How likely is she to enjoy the role?
What are the promotion opportunities?
What skills and experience will she gain?
Can she continue studying or consulting alongside the job?
Best-case scenario
She builds her own business
She earns more than she would in employment
She gains flexibility and autonomy
Worst-case scenario
Clients are scarce
Income is inconsistent
She misses out on available job opportunities
She burns through savings while trying to gain traction
Are people willing to pay for her expertise?
How much are they willing to pay?
How quickly can she attract clients?
What evidence exists that demand is real?
Second-level thinking reveals what information we are missing.
Many people assume the right information will somehow appear on its own once they start. It usually doesn’t.
The better approach is to identify the uncertainties and then deliberately investigate them.
Whenever you’re faced with a decision, don’t stop at:
“What should I do?”
Ask:
“If I do this, what happens next?”
And then ask again:
“And then what?”
That simple habit often reveals information that first-level thinking misses.
Hope it was helpful, I’d love to hear from you.
Comments
Nothing yet. Say the first thing.
Sign in to join the conversation.