Hello Friends,

Happy 2026!

Let's kick off the new year with confidence by confronting the things that are holding us back.

If you want your issue to be considered for an upcoming Newsletter, just fill out this form.

The Situation:

John has been providing free advice to a small company which has trouble achieving profitability due to a lack of business operational know-how. His advice has been insightful and his approach hands-on.

The CEO of the company, Michael has expressed interest in working with John further, even as far as to request for specific mid to long term deliverables that a one-time consulting engagement cannot fulfill.

John is interested to continue his involvement but is at a loss on how to scope out the work load and attach a fee that will fairly compensate him for his time and work.

John's excitement in this potential project is fuelled by his natural business instinct. He enjoys getting into the weeds to apply his strategic thinking to effect operational change.

However, John has his reservations in 2 aspects:

(1) Figuring out the amount to charge

(2) Presenting his fees to Michael

THE HOLLYWOOD TAKE

AMC's Mad Men has so many good examples of unfair contracts. Peggy Olson was up against working with people who did not reciprocate her efforts.

When she started out as a secretary, she gave beyond her role with zero recognition. She delivered free creative insight and copywriting work that were adopted but not credited.

Whilst I understand that it was a more challenging time for women to work in a male-dominated environment during a sexist era, Peggy Olson provided a ton of unpaid creative labor long before she received her well-deserved promotion.

SOCIAL SCRIPT:

Culture promotes the following ideologies - "Give before you take", "Be Humble", "Don't blow this opportunity by being greedy", "Who do you think you are?", "You've got to pay your dues".

All are true in some sense but if they are reinforced into a person who already lacks confidence, the person might not value their talents fairly.

In the movie, The Pursuit of Happyness, Chris Gardner (played by Will Smith) was so eager for an internship opportunity that he tagged along in a taxi ride (whose fare he was stuck with and couldn't afford). On the ride, he was so desperate for the executive's attention that he solved a Rubik's Cube just to get it.

I admire Chris Gardner's persistence but my lesson from watching that movie is to NOT WAIT until you feel desperate to ask for what you want.

Assess the situation plainly and don't overcomplicate it with your monkey brain.

If you want it, go forth and express your interest.

You don't need to have all the answers when you express interest, the details can be worked out by way of a dialogue.

INNER SCRIPT:

John's hesitation lies in believing the ideologies of the social script.

John's self-confidence can be boosted by going through his own LinkedIn profile. Going through his experience, the challenges he faced, the business models he fixed and the successes he had, will be a good way to remind him of his capabilities.

People pay for experience and expertise.

So why won't they be happy to pay John?

He should also be reminded that he has given Michael, the CEO, a taster menu of what it'll be like working together, so the "stranger danger" apprehension should have been dispelled.

John should also remember that Michael appreciates his work thus far.

ACTUAL SCRIPT:

When the time comes for John to present his proposal to Michael, he has more clarity on how to move forward.

John acknowledges his self-doubt and channels it into sounding out Michael's specific requirements and expectations.

They talk the specifics through, with John pointing out all the deficiencies in Michael's business and what it would take to fix them.

John provides Michael options that go beyond hiring John.

For example, what will the process be if Michael were to hire a full time employee to deal with the necessary OR to bring in a consulting company?

They run through the pros and cons of each approach, including their respective estimated costs.

With this FRAMING done, CEO Michael, has a cost framework in mind.

John, then presents his offering, as a solopreneur consultant with his own direct hands-on experience of being a CEO himself, and how that can benefit Michael's company.

He reminds Michael that due to their existing relationship, they do have a shorthand in how they communicate with each other.

He shares his working style and how he is focused on providing value rather than billing Michael by the hour. They talk about the project's target timeline.

Finally, John shares his service fee.

With that information on hand, CEO Michael, considers.

How it could work out:

Option 1: CEO Michael accepts John's proposal with some tweaks to the service deliverables

Option 2: CEO Michael bargains with John on his service fee and requests for at least a 20% decrease in fees

John takes that request into consideration but first tries to understand the pushback from Michael - is it due Michael's lack of resources OR is it due to Michael not valuing John's expertise OR something else?

With that understanding in mind, John makes a decision on whether it feels right to him to accept the project or negotiate further.

John reminds himself to operate from self-worth, to price his services for value (not time) and to only work with reciprocal partners.

Going forward, this approach will build John's self-respect.