The path to your first advising contract.

Not sure how to get started? Then this post is for you.

You work a traditional full-time role. But you are left longing for more. More flexibility, more deep/strategic work, more learning. Less meetings, less politics, less memos.

Advising seems appealing… but how does one get started? Well, don’t quit your full-time role just yet. Instead, set out to close your first advising contract in the next N months while holding your full-time position.

And this is your guide on how to do it!

Step 0: Set up

Before you get started, make sure nothing is obstructing your path:

1. Check your employment contract to ensure it doesn't specifically prohibit you from taking on side gigs. Don’t get yourself in legal trouble…

2. Do not engage with anyone remotely competitive with your full-time employer. It’s not worth it.

3. Discuss openly with your manager about exploring an advisory path to get their support and maintain transparency. It’s all about trust.

Step 1: Shift the narrative

If all you’ve had are full-time roles, all the hiring market will offer you are full-time positions. You must create your first advising opportunity; it won’t just show up.

Outbound rarely (never for me) works. But you have the power to shift the narrative in the inbound opportunities.

Don't ghost or decline the next time a full-time role knocks on your door. See if you can morph it into advising engagement instead:

1. Ask them, ‘Why me?’

   Understand why they are considering you. What about your background/skillset is attractive to them? This will help you understand your positioning and the superpower you can sell (back to them).

2. Assess feasibility

   Many companies are looking for full-time roles but don’t actually need the role yet. As a subject matter expert, assess whether:

   1. The company has people to execute; you can offer coaching as an advisor.

   2. The initiative can succeed with the following:

      1. Part-time contract: keep the bus moving while they find a new driver.

      2. Light touch involvement in prototyping viability.

See if you can change the mold of the opportunity instead of just blindly fitting into it.

Step 2: Pitch

Come out and say:

‘Full-time role is not right for me at the moment, but given my expertise in [my superpower/positioning] , would you consider [my alternative engagement]’ to achieve [your company goals].’

Be prepared to hear ‘No.’

And that’s ok.

You will hear ‘Yes, we’d like to explore’ eventually.

Remember, this process is similar to finding a new ‘product-market fit’ for your skills and will take time and a few interactions.

Step 3: Contract

Don’t optimize your first advisory engagement for money. Money upside will come later when you understand exactly what you are selling.

Treat it as your first learning experience. You will find out the following:

• What does advisory work look like day to day?

• Do you enjoy it?

• Are you good at it?

• How can you balance it with your full-time role?

• Do you want to do more roles like that?

Contractual terms should cover the following:

1. Monthly hourly retainer.

   You have a full-time role, and calendar stability is crucial. You are not flexible enough to spend 20 hours with your new client one week and 0 next. Ask for predictability with a monthly retainer, where the client pre-purchases a set number of hours from you. Start with 4 hours/month (an hour every week).

2. Hourly rate.

   Calculate your current full-time hourly rate and add ~30%. You will sign as a contractor without benefits or perks and must pay your taxes.

3. Monetize meeting hours.

   Tracking email/busy work has no value to your client. And it is a waste of time for you. Consider all time spent on the client to be baked into the hourly meeting rate.

4. Flexible termination.

   Have an option for either party to terminate the agreement immediately or with a 7-day notice. If it’s not working for either side, better to part ways.

5. Long-term engagement.

   Ask for at least a 6-month contract. Preferably 1-year. You hope to get learnings out of the engagement, which takes time.

6. Adopt their existing MSA/SOW.

   Ensure no clauses limit your employment options and that you can add a new ‘advisor’ title to your resume.

Compensation: cash or equity?

For your first contract, don’t stress too much about this question. Offer the company your advising hourly rate and ask their preference on cash or equity compensation.

But if you are going to take equity, keep the following guidelines in mind:

1. Ask for a monthly vest.

2. Ask for no cliff.

3. If equity has a strike price, you will owe money to the company at the end of the contract. You can deal with it by:

   1. Asking for an extended exercise window (5 years+) will hopefully derisk the value.

   2. Ask the company for additional cash compensation/end-of-contract bonus to cover the exercise amount.

Step 4: Iterate

You will begin noticing patterns after your 2nd or 3rd contract. This will validate whether you can become a full-time advisor or keep it on the side to spice up your mundane full-time life.

The hardest part is to get started.

So what are you waiting for?

Go to your LinkedIn inbox, search for all new opportunity outreaches you’ve received over the last three months, and GO FOR IT.