Why Your Business Needs to Repeat. To Repeat.

Let me ask you a question… What’s the best thing about having a job?

Not the worst thing (this is a newsletter, not a 12-part miniseries). The best thing.

For me, the answer is easy: Steady income.

Week after week, month after month, as long as you don’t quit, get laid off, or accidentally drive over the CFO’s foot in the parking lot, the checks keep coming. Sure, there are many negatives, but for the 15+ years I had a job, I never gave a second thought to money.

When you run your own business, on the other hand, it’s the mirror opposite:

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Your days can be exactly as you like – no boss, no commute, no cubicle, no fight to the top of the ever-narrowing pyramid. Your income, however, is extremely unpredictable.

It’s up, it’s down. It’s hot, it’s cold. It’s feast, it’s famine. One day you’re panicking about the mortgage, the next day you’re out pricing life-size, marble, penguin statues (or is that just me?).

Wouldn’t it be great, though, if you could have all the benefits that come with working for yourself AND … the steady income of a job? If there’s a Venn Diagram on Earth within which I would like to live (why am I talking like Yoda?), that’s the one.

But is it really possible to create this perfect, magical scenario? Well, when you put it that way, probably not. But you can get a lot closer to it than you may realize.

The key is in recognizing that all dollars are not created equal.

Let’s say, for example that you are presented with two client options: One pays you $15,000, once, up front. The other pays you $1,000 a month, out into the future. Which would you rather have?

There’s a lot of “it depends” in the answer, of course, but in general, I’ll take the repeat client every time.

Many reasons:

  1. The upside potential is way higher. I’ve got two clients whose email newsletters I’ve been publishing for 10+ years and several others for more than five. That’s a lot of money over a lot of years.
  1. Life is more predictable. When you do work on a repeat basis, you have work booked for the coming month before the month even begins. This smooths out the revenue and smooths out the workflow.
  1. You flatten the learning curve. Those 10-year clients of mine? It’s like clockwork. No miscommunications, no loose ends, no rework. They are easy to service.
    The new clients, on the other hand, are where all the gear-grinding takes place. You have yet to uncover – much less eliminate – the process issues that inevitably occur. No matter how wonderful these clients are, you are still learning how to work with each other.
  1. More cross-selling. People who know, trust and interact with you regularly are happy to buy more things from you. They don’t put it out to bid and they don’t haggle over price. As long as you have things of value to offer, you’re the first (often only) choice when new opportunities arise.
  1. Less time chasing; more time doing. The more repeat clients you have, the fewer new ones you need. Hunters spend most of their time stalking their prey; farmers just step out the back door and get to work.

Like I said, many reasons.

And while you may believe that a repeat element to what you do doesn’t exist, I’m pretty sure it does. Probably not your entire business, but parts of it:

Maybe you could … offer monthly, ongoing coaching to people who want to learn what you do, rather than just have you do it for them.

Maybe you could … offer a flat fee option where you update and maintain somebody’s web site or blog, or spend one day onsite at the client a month, or just be available for phone call consults at any time.

Maybe you could … offer a segment of your clients “front of the line” service, in return for a fixed monthly fee on top of whatever you already charge.

The point is, ongoing, “subscription” relationships are good for you and they’re good for your clients. And while you may never get to the point where you’re living entirely inside that Venn Diagram, every step you take in that direction will make your life a whole lot easier.

Special thanks this month to John Warrillow, whose book, The Automatic Customer, Creating a Subscription Business in Any Industry, (affiliate link) inspired today’s newsletter.

The book is filled with a ton of well-described examples and JW makes a strong case for why repeat client arrangements are so valuable.

What elements of the services you offer are on a repeat basis?
Post your comments below!

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15 thoughts on “Why Your Business Needs to Repeat. To Repeat.

  1. Laura E. Kelly

    Whenever someone asks me if I miss my old corporate job, I answer with a resounding “No!” But then I add that I DO miss the paycheck—both its steadiness and size. (-: Still, I prefer being a solopreneur.

    A big part of my business is helping other solopreneurs with their websites and online branding. These are things that will require steady maintenance, but very few of my clients choose to sign up for my very modest retainer. Yes, they are well educated by me as to why they will need assistance, but their cheapness outweighs this far-off future scenario and they say, “No, thanks.” Inevitably, of course, these people call me up out of the blue with semi-panicked requests for quick assistance. And because I am a helpful person, I nearly always help them, thus reinforcing their unprofessional behavior. (Then the bills are often so small that sometimes it doesn’t even seem worth billing them. Don’t worry: I do.)

    At one point I tried to make the maintenance part of my total services (You ask me to build your website, then you hire me to maintain it) but that didn’t fly. Besides trying to find clients with bigger wallets, I will check out John Warrillow’s interesting-sounding book for more enlightenment.

  2. Charles

    I still have my full time job (business consultant) and, I really enjoy it. I do my newsletter and whiteboard video business on the side.

    Each of my clients pay me to create and deliver a monthly newsletter, so it is recurring.

  3. Evelyn


    Yes, subscription and repeat work provide not only steady income but peace of mind. They help maintain my confidence too when other work isn’t coming my way. I write, edit, and publish newsletters and blog posts for clients on a regular basis. I like knowing that both the work and income are there.

    At the same time, I am happiest when I have a balance of repeat work and cameo projects. A few large brand development projects a year keep me learning and usually introduce me to new clients.

    Laura, I suspect part of your problem is that you aren’t charging enough for your work, especially the panic call segment. Not that you want to gouge solopreneurs, but I bet you have room to raise your rate to be fair to yourself and still be fair to your clients. Another way to do this is to have a one-hour minimum (I know Michael – not time based!) or a minimum charge, and not just charge for the few minutes the fixes take you. Plumbers and electricians have used this tactic successfully for years.

  4. Laura E. Kelly

    Thanks for your advice, Evelyn. I think you’ve hit the nail on the head! BTW, when I help them, I do charge them by the hour for even a quick fix, but it hasn’t deterred the calls and they won’t move to a subscription/retainer set-up. My husband suggested “Don’t even respond to their calls,” but turns out I’m not capable of that!

    1. Evelyn

      You’re welcome Laura. I can understand your husband’s position. My husband gets indignant on my behalf when he thinks clients aren’t treating me well too. But for a service business, not responding isn’t a long-term strategy and generally isn’t good for business.

      Better to reconstruct both your subscription and ad hoc offerings and build in advantages to the subscription. Maybe increase the price of both, but make the subscription a little less expensive and, as Michael suggested, promise to bump them to the front of the line. People understand a premium for emergency service. And what your selling isn’t really the fix but the relief that comes with knowing their problem will go away.

      1. Laura E. Kelly

        Great advice, Evelyn. I am rethinking how I position things for new clients, but also I have to figure out how to “retrain” or reposition all the past clients who come calling. They all knew about the modest retainer, just didn’t choose to sign up for it. Perhaps I should bundle that with the initial website design contract as just part of price of getting a state-of-the-art WordPress website (which will certainly need updating and maintenance).

        1. Michael Katz Post author

          Hi Laura!
          I think Evelyn makes some excellent points. Part of it is retraining, as you say. Clients learn how you respond and their crisis doesn’t have to be yours (unless you’ve made an arrangement otherwise). Don’t be shy about charging what you’re worth either. If you go out of business, nobody benefits, so it’s not to anyone’s advantage for you to be underpaid!

  5. Jen Carsen

    Great post, Michael! I do a fair amount of writing work for clients on a recurring monthly basis–other than one retainer-type arrangement (I handle whatever writing needs doing, within certain parameters), the others are all on a recurring project basis (X number of blog posts per month, etc.) rather than hourly, which I prefer.

    In addition to all the perks you mentioned, I’ve found another big one: The longer you do it, the more they start thinking of you as a de facto member of “the team” who is unlikely to be cast aside anytime soon (barring something like, as you mentioned, driving over the CFO’s foot–which, alas, has just as much career-damaging potential for contractors as it does for employees!).

    1. Michael Katz Post author

      Sounds like you’ve got things set up nicely, Jen. And that’s a great, additional advantage that I had not thought of.

  6. Mark Wayland

    Michael, at the beginning my business was structured around 2 or 3-day training programs with a few months of follow-up newsletters thrown in.

    Eventually I realized that what was far more attractive to my customers was to flip that offer.
    Now I write customized, bespoke newsletters for them and throw in a few days of training.

    This coming July 8 happens to be the 7th anniversary for one of my newsletter customers and that equates to about $89,000 worth of business.

    As Rene Descartes said, “I invoice, therefore I am” or at least if he ran a small business he would have.

    1. Michael Katz Post author

      That’s a nice flip, indeed, Mark. And a great example of how we can “do the same work,” but by altering the pricing/packaging, it can make a huge difference.

  7. Don

    One again you’ve hit the nail on the head, Michael. Securing repeat business is THE most important part of succeeding financially as a self-employed. I’m a freelance writer and most of my work is recurring: weekly articles and blogs, monthly and quarterly newsletters, etc. I’ll take one-off jobs if they’re worthwhile, but I charge more for them than I do for my clients with regular recurring work. Building a strong roster of steady, recurring clients has enabled me to mostly avoid the feast or famine that most freelancers experience. It’s the closest thing a self-employed will ever have to a regular paycheck!


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