Dot Your I’s, Cross Your T’s, And Get Paid

An independent professional in my network recommended I watch a talk by Mike Monteiro called “F*ck You, Pay Me” when I asked for advice on contracts and client relations. Whether you’re freelancing, consulting, part-time, or full-time, the advice given applies to any contract you sign related to your professional skills. Below is a summary of the video and I’ll also cover how this can apply to a full-time position.

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An Independent Venture: Customer Number… 0

Finding customers as a freelancer or contractor starting out is hard. These are some failed attempts at getting customers and what I learned.


Prospect 1: Work For Free

The first prospective client I spoke with was through a Slack networking channel. He saw when I posted I was looking for freelance work and asked me to join his other Slack channel that pooled freelancers. He said his team posted for freelance work needed on projects and those in the channel could claim the work.

This sounded fine. Until he described the work he needed me to do. For free. He mentioned that since I wasn’t an expert, he didn’t want to pay me. We spent some time negotiating  a lower fee with specific deadlines and expectations. It didn’t pan out and I got the impression he just didn’t want to pay for the work.

Prospect 2: Online Course Instructor

The second prospective client was found through Upwork. This position was for teaching a few lectures on common topics like Git, Test Driven Development, and DevOps. This sounded like a piece of cake. When I contacted the hiring department, we agreed upon expectations as well as pay. They asked me to do a sample lecture on a topic of my choice as an interview for the position. I did well on the interview. They sent me a contract to sign. And I never heard from them again. Sadly, I never got the contact info of the department that had reviewed and approved my interview, otherwise this might have turned into actual work.

Prospect 3: StartUp Chats

On several different occasions, I’ve met with CTOs, CEOs, or COOs of various startups to discuss potential freelance work. All of the startups are in the same position: they have a good base of engineers, they can’t afford to hire more, and they need a few more people temporarily to get their project to the next milestone. For each of them I described what specific work I could do on their project, for how long, and for what rate. Every single one of them said “I can definitely find a way to have us work together.” No, I didn’t really believe them but at some point one of them might be telling the truth. One of them was a friend of mine and he kept me updated on the contract progress. He was slowly suffocating under a mountain of work to the point where he didn’t even had time to list enough of it to create a freelancing contract. I’ve chosen to assume that all of the startups have similar challenges and won’t sweat the loss. On the other hand, I also gave them my contact information rather than getting theirs. This meant I couldn’t follow up with them. Now I know I always need to get a business card.

How did I meet these people?

Learning From Failure

I don’t see these failed attempts at landing clients failures since each time I learn something new. With the first client I learned that people will ask me to work for free and I need to be firm on saying no. With the second client, I learned that talking to hiring departments is a waste of time if my contract will be with a different department. With all the startups, I learned the importance of following up. A little nudge is enough to get you a lot of work.

An Independent Venture: Freelancing, Contracting, and Consulting – Oh My!

Recap: Traditional full-time work isn’t a good fit. This is a post exploring what the more flexible, self-employed work options look like.

choices decision doors doorway
Photo by Pixabay on

All of the different types of work discussed here have these things in common (except Startups):

  • Not working full time for a specific employer
  • Define a fixed amount of work or time doing work for another company or person
  • You are responsible for managing and reporting all of your taxable income
  • A ramp up time of at least a month before you start getting income
  • Full responsibility for equipment, resources, and software for work
  • Choice of how much to work in a day, week, year, or month

Note: I phrasing these from the perspective of a software developer.

Another Note: You can mix, match, and combine any or all of these options.



What’s different about freelancing?

  • Projects can be very short
  • Clients are often individuals or small companies
  • Complete control over how much you work and what work you do

Money Matters

Minimum time to profit: You can pick up a freelance job the same day you decide to freelance.

Minimum time commitment: Jobs can range from a few hours of work to several months or years of work.

Income variability: Highly variable. You can control this more with contracts that require deposits before project work or payment upon receipt of milestones in a project.

On the Job

Getting work: Networking, freelancing sites, classified sites, your dad’s golf buddy’s nephew’s small business.

Types of work: Work ranges from very small specific tasks (write a script) to large scale projects (build an e-commerce website).

Types of client relationships: Highly variable. Some clients will be ignorant of what your work is and demand impossible tasks with impossible timelines for nothing. Other clients will understand your industry skill sets and value you fairly. Good news: you get to pick your clients.

Is it for you?

Ideal for people looking for:

  • Variable length projects
  • Low in-person interaction and minimal interaction overall
  • No “sales”


  • Market dependency: demand and rate will vary depending on where you are getting work
  • You need to take extra care to protect yourself from bad clients
  • It will take time and effort to increase your profits, though you will be able to make some money quickly



What’s different about contracting?

  • Work contracts with a single employer
  • Employer sometimes handles taxes and administrative tasks for you
  • Time based rather than task based
  • Consistent income

Money Matters

Minimum time to profit: This is the same amount of time it would take to find a job posting, apply, interview, and get your first paycheck. About 1 to 2 months.

Minimum time commitment: Short contracts are about 3 months.

Income variability: Stable. You’ll be paid regularly as part of the contracting work.

On the Job

Getting work: This type of work can be found on job-boards and through recruiters. There are also agencies and contracting companies but you can fall into being a full-time employee of those companies rather than working for yourself.

Types of work: This is most similar to regular full-time work where you have a set of responsibilities rather than a specific project. You’ll often be working full-time but part-time contract positions do exist. Similarly, a lot of these request on-site contractors but some can be remote.

Types of client relationships: Very similar to employer-employee relationship. You’ll often be talking to recruiters and “contingent staff managers” as your hiring clients but you will be working with a team manager for day to day work. Your clients in this case will be medium to large sized companies looking for “contingent staff” to temporarily bulk up their workforce.

Is it for you?

Ideal for people looking for:

  • A regular work routine with a single company with consistent pay
  • A fixed term full-time employment with a clear end date
  • More security provided by the hiring company
  • Less administrative work
  • Working on teams with other people


  • You may not be seen as “equal” to full time employees
  • You can’t choose your hours
  • You may not be able to choose your location


What’s different about consulting?

  • You own your own business
  • You need to sell and market your products to potential clients
  • Your client relationships may be longer term with many repeat clients

Money Matters

Minimum time to profit: 6 months or more. You will need to build up a business, advertise your services, come up with portfolio data, and identify clients you can sell to.

Minimum time commitment: 1 – 2 years. You can be a consultant for 1 month but you’d ideally want clients that are looking for longer engagement of your services.

Income variability: Moderate. If you have long term clients, you will see some stability in income but depending on how consistently you get clients, it could be more variable.

On the Job

Getting work: networking, former employers, friends of friends… of friends

Types of work: Bigger projects with longer term or permanent involvement. Permanent involvement might mean that you are available to provide support work for a defined fee after the initial project contract is done.

Types of client relationships: Your goal is to have repeat clients and a steady flow of new potential clients. The clients will often be businesses and not individuals. You’ll be offering a complete and self-contained service to them. Ideally they recommend you to other businesses or return to you for more business.

Is it for you?

Ideal for people looking for:

  • Work scoped to a specific skillset
  • More decision power over how work is done
  • Lots of interaction with clients
  • Potential for expanding into hiring other people to work with you


  • You need to have marketing and sales material publicly available
  • You need to be comfortable doing sales to sell your consulting services
  • A miscalculation at the beginning of creating your value proposition and selecting your clients could result in the wrong clients or no work at all


What’s different about starting up your own business?

  • You own your own business
  • You are not dealing with clients but trying to engage customers instead
  • Marketing and sales comes after development and is targeted at groups of people rather than specific individuals
  • You are selling a product, not a service or a skill
  • There are significantly more administrative tasks to consider

Money Matters

Minimum time to profit: Months to years depending on the type of product you are selling. If you are building a simple phone app, it could be weeks or months. If you are building  website or service, it could be months or years.

Minimum time commitment: This one is tricky because you want your product to last long enough to make money. I’m going to throw 2 years out there as a minimum.

Income variability: Technically, the income isn’t variable since you won’t have any income fairly consistently until your product is out in the market and people are buying it. Often you’ll get a single lump sum investment and then nothing again. However, there are some ways to get variable income as you are developing. These are things like Kickstarter and Patreon.

On the Job

Getting work: You make your own work.

Types of work: You decide what work you are doing but be prepared to do everything from janitorial work to client calls to bug fixes for your business.

Types of client relationships: There are no clients; there are only customers.

Is it for you?

Ideal for people looking for:

  • A way to share a great idea they have with the world
  • Complete control over an entire product including inception and maintenance
  • A long term investment that might turn out to be extremely lucrative
  • Lots of variety in their work tasks


  • Your idea has to actually be good and you must be able to execute well
  • Market competition for your specific product or lack of demand
  • Inability to monetize in a way customer are willing to pay
  • Due to the long term investment, lack of follow through to completion