An Independent Venture: Before You Go…

At this point, I’ve decided to stop working full time. I considered a few different things before starting self-employment.

Disclaimer: I haven’t fully tested this advice so stayed tuned to see if this worked or not.


If I’m actually going to do this thing, I’ve made sure I have thought out, defensible reasons to drive me and keep going through the hard parts. It is scary to quit something stable that works well and that “everyone” tells me is the greatest thing that ever happened to me. There will be a lot to learn with surprises along the way. People before me have been successful in this and I can be too… as long as I have the fortitude and grit to keep going.


Have them. This feeds into motivation as well and can help with some unexpected decisions. By choosing work based on goals, I might actually achieve them. For example, if I want to be primarily remote, I’m going to have to keep that in mind when Some Large Tech Company offers me a wonderland of benefits, high pay, and perks… in exchange for on-site work only. Then I’m back to square one.

Examples of goals I’ve considered:

  • A flexible work schedule
  • Freedom to choose projects and clients you want to work with
  • Freedom to learn a new skill and use it on the job right away
  • Able to work in any physical location
  • Variety and excitement in your work life
  • Being able to meet a diverse group of different people regularly
  • Far more interesting tax returns

You might think, “these don’t sound like goals, they sound like tenets“. Call it want you want – “North Star”, “Tenet”, “Guiding Principle”, or “Goal” – you (or I) need to be aware of the factors that help make or break decisions with arranging work,  life, and the fact that they’re about to become the same thing… if they weren’t already.

Digression on Goal Specificity: Flexibility

To clarify the level of detail in my goals, I will go into a more thorough explanation of what flexibility as a goal looks like to me. I have achieved the goal of flexibility if:

  • I can choose the number of hours I work proportional to how much money I want to make. If I work 10 hours, I get $10; if I work 20 hours, I get $20.
  • I can shift my work hours by days, weeks or months in order to create significant gaps in my work schedule for something like travel. I can work January to March and take April to travel to Japan for cherry blossom viewing.
  • I am able to choose my location of work 80% of the time. I can work from my home, someone else’s home, or a hotel for a large duration of a project (8 days of a 10 day project).

By working towards this goal I want to find out the following things:

  • How many hours per week is ideal for me within a range of +/- 5 hours
  • What are my optimal work times during the day or week
  • Am I more productive with short bursts of concentrated work or steady streams of work over longer periods of time.

As I drill down into these ideas of what I want to accomplish, I turn it into an experiment to make me a productive human in a way the full-time workplace couldn’t. If by some ironic coincidence I find out that I’m optimal for a concentrated, non-stop, 40-hour work week year-round, I suppose I’d go back to working for large tech companies.

As with development, it helps to establish a target even if I don’t get there. It helps orient  a scale, time frame, and organizes my values so I can say ‘no’.


It turns out I need money or “funding” stashed away somewhere if I want to quit my job and not work for an extended period of time. Short story: I determined how much money I spend in a given period of time (let’s go with a month) and how much time I ramp up time I need. So, if I spend $10 per month and plan a month of travel and then 3 months before earning sustained income, I get $40. There are many “rules of thumb” out there that will give values like “3 months worth of pay”.

I also considered running out of money with the goals unmet. This means finding a safety net or backup plan, like Mom’s basement. I also needed an idea of when to hit the “eject” button. I don’t wait until you have $1 left before realizing I need $500 to move my stuff to Mom’s basement. Or more realistically, pay for my internet bill to do that phone interview to get the job I now can’t afford to turn down.

There is a ton of discussion on finances out there and I’m not an expert so I won’t go into it more. If you have recommendations on your favorite finance resources, I’d love to hear about them.

As a side note, starting a low-rent apartment complex called “Mom’s Basement” just for kicks suddenly sounds like a great idea…


“What is your personal brand?” is a question I usually avoid. However, if I am selling my skills directly to clients, I need to have one and it better be the one I picked. Picking a brand usually relates to “what do you want to be known for?” or “what do you want your customers to ask you to do?”. If people keep requesting SQL database migrations even though I really want to be a Ruby on Rails developer, something is wrong with my goals and my brand. People will learn about me from word of mouth and my work portfolio. If I accept and do jobs in an area, that area will be part of my brand.

Work style also contributes to how clients and customers see you. Do I insist on fully remote? How often do I meet with customers? Do I often deal with individuals directly or through others? Am I charismatic or overly technical? Whatever I want to be seen as, I try to be intentional about how my actions form my brand. It will impact the type of work and clients I get. It’s hard to change a personal brand once it has started to morph into a monster of its own.

All Your Base

Finally, once I have motivation, goals, money, and brand more or less ironed out, I need to get going. I think of this as “establishing a base” and it consists of the following:

  • Physical work location
  • Work setup (computer, developer accounts/software, contract templates, work email, comfy chair, fancy desk, desk toys…)
  • Client pipeline and advertising
  • Methods of professional development

Honestly, I really just need the first three. I added the professional development because I will be better able to advertise and network if you are current in your area. It’s also yet another venue to get work through conferences or courses.

Another disclaimer: this is how I got into the mindset of being ready to embark on self-employment. I heard other people reach it accidentally or unintentionally. I’ve heard stories of less preparation. I’ve never heard stories of more preparation. I suppose that says more about me than anyone else.


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