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.

Read More »

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


An Independent Venture: Sales?

I was at a software conference and met up with someone in marketing. I asked Marketing Friend for advice about how to negotiate sales and land clients for my business. Here is a digest of the advice she gave me.

It Turns Out There Is Something In A Name

First things first: how do people know you? Not only that, once they know you, how do they remember you? Despite what certain inventors of English literature may write, there can be quite a bit in a name.

  1. You need a name
  2. Your name should be associated with you
  3. Your name should be memorable

You might think (1) is a little silly but at this point in my business I had no name so I was confronted with an existential crisis every time someone asked where I worked.

If you have a larger company, you may not want to  associate it directly with yourself but rather with what your company identity is. I work on my own so I can make the company name more personal. If you can find a personal trait to coerce into a memorable and catchy name, you can create something that helps people remember both you and the company.

Example: If you have a common name with an alternate spelling, use the corrective phrase as a title. This is contrived but if your name is “Joan” but spelled “Jone” then you can have a company named “J number one” or “J – 1, 2, 3”. This is both personalized to you and helps your clients associate you and your company together.

Bad Example: I have a silent ‘d’ in my name, which Marketing Friend noticed right away. She said, “Call your company ‘With a “D.”‘ For what I hope are obvious reasons, I’m not going to go with that one. It would definitely be memorable though. Not safe for work reference.


A.K.A. Gathering Competitive Information

You will win bids and you will lose bids. Every win is an opportunity to strengthen the positive aspects of your sales and every loss is a way to identify gaps and shrink them. When you lose a bid, take the loss gracefully and use this opportunity to get information about the winning bid from your formerly potential client. This will almost be the only time you’ll get this information because you’re playing on guilt in the client. Remember this needs to be done as an immediate reaction to the rejection of your bid.


Client: “Hi Alacritical, I just wanted to follow up to say we’ve decided to go with another consultant for this project.”

Me: “I understand and I’m glad you found someone you want to work with. If you don’t mind my asking, what about that team made them stand out to you?”

This can be a fishing expedition but I hope to find out about what the competitors bid is and whether they had some marketable edge over me.

Sell Like A Vampire Hunter: Straight Through The Heart

It turns out humans aren’t robots. It can be disappointing news, but there you go. We have feelings in addition to logic and often we aren’t aware of how this affects our decisions when we think we’re being logical. That’s a whole other discussion though. When you are telling a story, making a joke, or selling anything, you need to hook that emotional part of a person and show them how what you are saying relates to them. Once you’ve got that attachment, you can let that robot logic make the decisions and spit out all the data and numbers you want.


  • A sales pitch is a story
  • A story has a beginning, middle, and end
  • The beginning draws people in through emotion and a clearly identified challenge
  • The middle describes an action in response to that challenge
  • The end is how that action resolved the challenge and addressed the emotion at the beginning


You want to pitch a service where you audit a cloud software system and identify cost savings areas. What are the different parts of this story?

  1. Emotion: You’re looking to play on the fear of losing money, the pressure of increasing profit margin without increasing resources, and the avarice of taking more money home
  2. Hook: Build your hook with a clear definition of the challenge and emotion. This means using language that evokes emotional responses. “Are you sure you could see the invisible leaks draining your infrastructure funds?” “Do you find yourself squeezing your budget for more research funds? Look no further than your own infrastructure as a bounty of potential savings.” “What would you say to boosting that profit margin with some simple streamlining techniques to your infrastructure?”
  3. Action: Describe what action you can take to solve this problem and address that emotional response you just played on. “We will use our team of skilled infrastructure engineers to dive into your infrastructure to deeply understand what your needs are. We can always find ways of lowering costs without lowering quality, engineering happiness, and ease of maintenance.” Note the continued used of evocative language. Also note use of the second person voice. You want your client to feel like this is something you’re doing just for them even if we all know that’s not true.
  4. Happily ever after: This is where you can start throwing in some data. Talk about success stories and what they got out of your services. “As a result of this work, we’ve empowered small and large businesses to re-invest almost 25% of their previously wasted infrastructure funds into innovation and growth.” Perhaps with a strong implication that we can do this for you too.

I personally don’t like the part of sales where I need to use emotionally charged words or topics to trigger attention or attachment but the good news is, this works for telling jokes and making effective presentations too. Check out TED talks and other advertisements to see if you can identify each of the components of the story they’ve created.

Client Communication Guidelines

Good news, you did the sales part and now you can just relax and treat clients like a regular person? No. It’s not going to be as much of an effort but you need to respect that they are running their own business and they are the center of their own universe. What does this mean?

  • Do not sound like you’re reciting a one-size-fits-all response. Personalize to show that you are making this proposal for them specifically. “For you, I recommend…”, “Something that will work well for your system…”
  • Do not use jargon. Use simple and direct communication. Take a look at the way they do news bulletins on television and how they can be understood by most high school students without difficulty.
  • Spend time focusing on making sure they see you understand the problem and are there to help them cope with it instead of throwing a solution at them and walking away.
  • When proposing alternatives to a solution or suggesting a solution to a separate problem you have not been asked to solve, always empower the client to make the decision. Present your suggestion in a way that highlights the differences (i.e. even if the change isn’t visual, a visual difference is easier to understand). Propose objectively and respect their choice.
  • See if you can connect with individuals closest to the problem to gain the best level of understanding. This can also smooth some turbulence caused if you indirectly create work for others before you’ve talked to them about the work.


There were a few phrases that, as a “radically candid” person, seem okay but Marketing Friend told me to adjust:

  • “Renegotiate” should be “Modify” – renegotiate is scary and will lead people to close down and back away despite its accuracy.
  • “You can’t afford me” should be “This isn’t a good fit” – Being a woman in tech, I’m repeatedly told to assert my value. Just not with clients it turns out.
  • “You say you can’t afford me but I guarantee I’ll do a great job and it will be worth it” should be “I really want to work with you on this project; don’t let money stand in the way” – This communicates that you are committed to doing a good job on the project but also that you’re not just selling the service, you’re selling your emotional investment as well. Thus, selling your heart.

Notes on Being a Woman in Business

We hear a lot about how gender stereotyping harms women in business, politics, the home, and basically everywhere. However, there are some ways women can leverage this in sales.

It is more acceptable for women to show emotional and caring according to gender stereotypes. As a result, women can show much more emotional attachment to potential clients and highlight their caring and supportive strengths as an asset. If you can find someone who can do the job and actually cares about how it affect you, why wouldn’t you choose them?

This is not to say you should sell your heart to these companies. When you genuinely are interested in delivering a service and want to show you care, do so. This is about letting that extra bit come out in your sales.

Example: Say, “I love the ideas and innovation you’re bringing to this market and I want to be here to support you through building this vision” instead of “I find your ideas and innovation interesting and I’d like to contribute”

Now, this is a touchy subject. I’m not saying men can’t do this. They can. However, due to the unfortunate restrictive bias of gender stereotypes (remember, they’re not good), men may be seen as weaker for showing this kind of emotion. Weaker means less trustworthy to some people. It’s unfair. I’m sure men all over North America are just crying themselves to sleep at night with that extra $0.20 on the dollar they make over myself and other women.

Note: I did intentionally choose an article that both explained and contradicted that number for maximum fairness to everyone.

The End

Remember, these are just notes and ideas from me and my marketing friend. Everyone works differently and all I can hope is that trying this out will make a few more interesting blog posts to write.