Applying The Principles Of Kaizen And Bootstrapping To Build Your Freelance Skills

Many of us freelancers are content creators, whether in terms of written content, design, or coding. What if you’ve had enough with current freelance gigs and want to move in a different direction with your skills?

Not factoring in change can be a quick path to freelance burnout. For example, the NY Times recently had an article about making money as a casual web video producer. Whether that’s what you want to do or not, how do you find the time and budget to transition into a new skillset?

How to Transition

Your constraints are a minimum of time and a minimum of budget. Of course, if you find a way to monetize the new skillset, you can commit the time for learning and producing, as well as the budget for acquiring whatever you need. The key to the process is to ensure that you don’t have to adapt a “this only” or “that only” mindset. You can ease into your new skill set, as well as into financial commitments, all the while earning something to make the transition worthwhile. If you apply both the principles of Kaizen and bootstrapping, then transitioning becomes a process that you can control. This does not mean it’ll be easy, but the process will be manageable.

What is Kaizen? What is Bootstrapping?

I wrote about both Kaizen and bootstrapping at about bootstrapping business more extensively at Bootstrapper (though you may need to search Bootstrapper for the older archives). In a nutshell, Kaizen was originally applied to manufacturing processes, but can be adapted to pretty much anything in business and personal life that requires improvement. It means to apply small incremental and continuous improvements to a manufacturing process, product, service or a skill. That is, don’t try to be everything to everyone all at once:

  1. Define a manageable initial target.
  2. Achieve the initial target.
  3. Define where you want to go from there with your offering.
  4. Plan the next stages of improvement in manageable segments, including expanding into multiple but related offerings.
  5. Apply what is necessary to achieve the next stage’s target.
  6. Repeat step 5 ad infinitum (or as necessary)

Bootstrapping is the financial side of the incremental improvement equation. Many successful businesses have been bootstrapped, simply by following a few simple rules:

  1. Spend the absolute minimum for what you need (equipment, software, services, hires) to keep your business running.
  2. Reinvest as much of the gross profit as you can to improving your offering. Funds might gradually be spent on:
    1. Taking courses/ training.
    2. Buying books/ magazines.
    3. Joining professional organizations.
    4. Getting access to premium online content.
    5. Adding new hires.
    6. Buying equipment or software, possibly to upgrade what you have.
  3. Take little to no net profit. Simply take enough to live on, but not to the point of your detriment.
  4. Repeat steps 1 and 2 until the point where you have a net profit to speak of. (As a freelancer, I never make the mistake of thinking I can have a self-sustaining business. That only comes if you expand with new hires, where you’re leveraging OPH – Other People’s Hours – into your own profit. That’s not typically something the average freelancer does because then you’ve transitioned into more of an entrepreneurial role.)

Of course, time is money, and if you spend most of it earning a living, then you also need to factor in time spent into the bootstrapping equation. The more you earn from your new skills, the more time you can put into the transition process. If something goes wrong, or you reach a temporary plateau, you still have the fall back of your existing skills.

A Suggested Transitioning Process

The web makes it so much easier to bootstrap, especially if you are content producer. This is thanks to all the free browser-based software available, not to mention 30-day fully functioning trials of many categories of software. If you do a bit of digging, you can sometimes find enough different trials of one type of software to keep you going for months without spending a cent. And if you manage those “free” months well, you can simultaneously apply Kaizen principles to improve your skillset and content offering while spending little or nothing.

You might even earn enough during those “free” months to pay for new equipment and software, when your trials run out. That’s the type of bootstrapping that online entrepreneurs have to apply.

The benefit is that during those free months, you might find that you feel less pressured to produce something simply because you’ve neither spent a fortune nor set your standards high. You can also ease into the skills improvement commitment.

Let me present a generic process first, then expand with an actual example below.

  1. Download and install free software, or use free web services. In any given category, there are often 15-, 21-, and 30-day fully-functioning trials. So make a list of all such trials for a specific type of software, then stagger your downloads so that you get maximum “free” time out of these. This buys you the time you need to get started, and to decide which package you like best.
  2. In the meantime, start browsing books, magazines and websites/ blogs that cover the niche you want to learn. You don’t necessarily have to dive right into indepth learning just yet. Start taking casual notes, to set the stage for the learning process. If you’re fortunate, you’ll find what you need online or in your local library – thus having to spend nothing.
  3. When possible, select some web-based or local courses. Spend time researching and pick one or two of the most suitable courses. You’ll have to decide whether you’re a beginner, intermediate or advanced student. If you’re going into a wholly new area, I suggest beginner. (Follow the advice about the monk who told his student to empty his “cup” of knowledge, in order to learn. And for those of you who’ve seen the movie The Forbidden Kingdom, starring Jackie Chan and Jet Li, this advice long predates the movie.)
  4. When you feel confident enough that you can produce some content with your new skills, create some samples. You might need to spend a bit of money, but if you can justify this in the next step, it’s worth it.
  5. Use the samples to get buy-in/ commitment from clients, sponsors, partners. This might be a short-term commitment to test some real content, with a long-term commitment following that. If you have even a small financial commitment, then you’ll feel more confident in doing any or all of the following:
    1. Investing in more education. Maybe there’s one course you’re itching to take, or a website that offers premium content to paid subscribers – content that will fast-track your learning the skills you need.
    2. Investing in a few tools. Don’t go crazy just yet and buy a rack full of gear. Just by the next most necessary item, in order to produce the next level of quality in your content.
    3. Investing time in learning and in content production. Produce a few incrementally higher quality content samples.
  6. Use the new samples in step 5.3 to get a longer-term commitment, and to finance additional tools, education, hires, and content production.

Example: Building From Podcasting Skills to Web Video Skills

Referring back to the NY Times article about the increasing demand for web video content, let’s look at how you would move from no skills in web video content production to becoming an expert. The follow example is very┬áspecific, but you should be able to extract the general principles and adapt them for what you would like to do.

Stage 1: No skills

This is your starting point, where you have little or no skills in the area you’d like to move into.

Stage 2: Build podcasting skills

This is an optional step, though if you take the time to complete it, you’ll learn voiceover skills.

  1. Learn what you can online about podcasting.
  2. Invest in either a portable digital recorder or an inexpensive microphone that can connect to your computer. (USB interface is the simplest.)
  3. Download the free Audacity audio editor.
  4. Get the hang of recording a podcast, say a series of reviews of various software tools that you use for your freelancing work. If you supplement the audio series with articles, you might be able to sell the package to a site/blog and earn back the cost of the equipment.

Stage 3: Move from podcast audio to podcast video

Once you’re comfortable with podcasting, the next stage is to turn your audio series into a video slideshow version. (You’re not doing any video shooting or screencasting just yet.)

  1. Find a screen capture program that lets you grab still shots of your computer screen. I use TechSmith’s SnagIt ($$) and Wink ($0), but there are others, some free. Some screencap programs work from directly from your web browser, which makes them useless unless you’re only using web browser software.
  2. Combine your audio recording with a series of still images.
  3. Learn how to add titles at the beginning and production credits at the end.
  4. Produce a “video” out of the arrangement. The result is a sort of slideshow with audio.
  5. Once again, the review or how-to theme is most likely to be salable.
  6. Save the funds for screencasting software.

Stage 4: Move from podcast video to screencasting

If you’re comfortable having moved into pseudo video production, try screencasting on the cheap.

  1. Get free screencasting software, Camstudio (Windows-only), or something inexpensive that will run on non-Windows operating systems.
  2. Produce a tutorial about some software, preferably something that will not cost you anything. (There are hundreds of new web browser-based applications for you to choose from, as well as free trials of desktop software.)
  1. Choose your software.
  2. Decide what functionality you are going to discuss.
  3. Get familiar with the software, especially that particular functionality.
  4. Turn on Camstudio’s recording feature and capture a session of you using the software. You can add voice simultaneously, or later on in a video editing program. (You’ll have to take your pick, depending on your computer. There are some 30-day trials that are fully-featured.)
  5. Add pan and zoom elements, to show detail in the screencast.
  6. Add titles and credits.
  • Take some screen still shots to show greater detail.
  • Write an article, with the screen shots, to go with the video screencast.
  • Sell the package to a site or a blogger.
  • Save the funds for a more sophisticated screencasting program such as TechSmith Camtasia Studio, and for the next stage.
  • Repeat steps 2-6.
  • Stage 5: Combine screencasting and live footage

    Screencasting can get boring for both content producers and viewers. To add some visual texture, you might consider adding some live footage, say of the tutorial host/ reviewer. However, you’re at a stage where’ll you have to not only spend increasingly more money on equipment and to learn skills, but more time to produce the video content. You have to feel you’re ready for this step, and that there’s enough reciprocal benefit. Here are some possible additional expenses at this stage:

    1. Video camera. You don’t necessarily have to buy an expensive professional camera, unless that’s a requirement of the client. If it is, and if you can’t afford it, consider renting.
    2. Videotape, batteries/ recharger, tripod.
    3. Video capture card/ unit, to transfer recordings from your camera to your computer.
    4. Video editing software. Though you can often get a free 30-day, fully-functioning trial of programs such as Sony Vegas Pro.

    Stage 6: Progress to live footage

    You’ve now combined some live footage in your video content. If you’re comfortable with the workflow, and it has been worth your time financially, it might be time to move into full video work. Video “how to” sites like Howcast and Expert Village explain what they are looking for, what they pay, and how their process works. The work that these two sites offer requires professional-level cameras. (Other sites may not.) Maybe your city has a video/ filmmaker collective that allows members to cheaply rent equipment and facilities.


    1. Script your video. Use a natural “voice”. Read it out and revise it until you’re satisfied.
    2. Storyboard the key frames, so that whomever is shooting the scenes will know partly what you’re trying to achieve. Storyboarding for video, even how-to/ tutorial videos, isn’t all that different than storyboarding for film.
    3. Hire a crew if necessary: actors/ expert host, videographer, director. (At the least, you should take the role of “producer”, where you do all the project management.)
    4. Shoot the video.
    5. Edit the video and arrange the segments and audio dialog.
    6. Re-record audio portions, if necessary.
    7. Add background music and any narration.
    8. Add titles and credits. (This includes any onscreen text that you want to add, to clarify segments of the video.)
    9. Render your final video to the desired file format. (This will depend on who is buying from you or where you’re uploading to.)
    10. Sell to a client, or upload to a video sharing site where you’re registered as a “producer” who will receive benefits (either paid per project or on the basis of number of views).

    Potential additional expenses at this stage:

    1. Professional video cameras – probably HDD (hard disk) cams are best. Rent or buy.
    2. Greenscreens.
    3. Advanced gear – microphone arms, more microphones, dollies, etc. It all depends on what kind of work you are doing. Again, you can rent, but your project management skills had better be sharp or it’ll cost you more in rental fees.
    4. Video editing workstation(s).
    5. Hired videographers, directors, actors, etc.

    Stage 7: What’s Your Stage 7?

    For me, Stage 7 will be a transition into filmmaking, possibly only for the web, if it’s lucrative enough. I’m not after a mega-multi-million dollar lifestyle. I also don’t want to be bound by the same kinds of bonds that chafe as an employee. I’m a freelancer at heart, and the web offers many opportunities for freelancers producing a variety of content.


    It’s my belief that web-working freelancers will need to stay regularly updated in their skills. Being on the cutting edge of online content production gives you an advantage. While freelancing gives you freedom of choice in terms of work, you’ll still need to learn at least the basics of new skills. If you adapt the processes above, and make your new skills work for you, you can also consider hiring out for the skills that you don’t have the time and/or budget to learn.



    About The Author: Raj Kumar Dash is a long-time freelancer/ web consultant, an experienced and published writer, a published author, former print magazine publisher, retired programmer, hobby composer and short story writer, and aspiring filmmaker and screenwriter. Past blogging gigs included paid or guest posts at,,, editor of Bootstrapper, editor of a travel blog network.

    Currently he is a lead blogger at, and a weekly contributor to FreelanceSwitch and FreelanceFolder.