Where Successful Freelance Bookkeepers Get Stuck

In the beginning, when trying to become a successful freelance bookkeeper, it might seem like the hardest part is getting those first few clients. Once you get two or three, you’ll be on your way.

And for many, getting past that initial startup period, you think it's smooth sailing from there since you’ve got what you wanted. Some paying clients and steady monthly work. It's simply a matter of growing from here. Often we’ll get our next few clients via referral, and if we’re eager to grow quickly, we’ll develop a few marketing strategies to bring in more clients on a regular basis.

But once you’ve got some momentum, there’s a shift that happens. Instead of having the profitable bookkeeping business we envisioned, working as your own boss, and making good money, we get stuck. This next hurdle can be far more difficult to get past.

The Success Problem That Can Kill You

Suddenly one day a sales tax filing deadline unexpectedly creeps up on you, and you have to work a few extra hours over the weekend to get caught up. Or your holdout client who’s been clinging to QuickBooks Pro 2007 finally agrees to embrace the cloud and move to QBO. He wants to know how quickly you can complete the conversion so they can be up and running ASAP.

While this is great news, you’re currently in the middle of completing a massive new client cleanup project that you promised would be done early next week. Then immediately after that you've onboarding and training scheduled. You wonder how to possibly fit all this work in and still make it to your daughter’s big dance recital on Friday. And of course, you're  way behind in updating your own books (has it really been 8 months?!). Oh, and it completely slipped your mind that the mortgage payment was due last week. Yikes!

If you’re not already there, you’re headed into the pit of working far too many hours, making less money than you should, and feeling exhausted, frustrated and a stranger to your family.

But it doesn’t stop there!

Once we’ve hit overload, we realize that we have more client work than one person can get done during normal working hours. We're already working way too many hours. So it must be time to hire employees, or at least contract virtual staff. But that can actually make matters worse if you’re time is already overstretched.

Hiring help involves a steep learning curve that includes creating job descriptions and defining responsibilities, searching for and screening potential candidates, training, and what most of us have no experience with… people management. It's also a big financial commitment.

But you dive in anyway. It's the price of “success” after all, right?

But now you need to work even more hours than before (with even less productivity since you’re constantly interrupted with questions or pleas for help from your team). Your overhead has skyrocketed and your cash flow is crunched. What really stings is you're paying yourself even less money than before you hired “help”!

Staying stuck in this rut brings with it huge amounts of stress. According to the Mayo Clinic, “Stress that is left unchecked can contribute to many health problems, such as high blood pressure, heart disease, obesity and diabetes.”

This is not a sustainable way to run your business or your life.

Finding a Way Out

While this path is a typical one, the way to get off of this insidious treadmill is not as clear cut. Certainly, though, it is a time to pull yourself out of the weeds of the actual day-to-day work and step back to work ON your business. We need a fresh perspective.

Some questions to consider that may lead to successfully stopping the insanity are:

  • Do you need defined, effective systems to improve productivity and consistency?
  • Would adding automation improve efficiency and save time?
  • Do you need to overhaul your pricing structure?
  • Do you have the right kind of clients and would you benefit from specializing services?
  • What are your business goals beyond simply making a living and paying the bills?
  • Do you have an ultimate vision for your business and your lifestyle?

We all need to consider questions like these on a regular basis. In fact, building a habit to do so can make a big difference in the direction of your business. I’ve seen it in my own bookkeeping practice. Though I must admit, after many years in business, it seems I slide back into this overwork cycle whenever my practice starts to grow with new opportunities.

In fact, learning how to find and maintain a work-life balance is a particular challenge when you love what you do. And of course most of us want to (or need to) increase our profit levels as well.

That’s why I’m so excited to have Steve Pipe, a Chartered Accountant and author from the UK who is one of the most highly regarded accountant advisors to our profession in the world as my special guest on a brand new (free) webinar I’m hosting: “The 3 Keys to Profits & Work-Life Balance” coming up on Tuesday, October 24th at 12:00 noon Eastern Time.

Steve has learned how to navigate these overwork pitfalls himself and not only successfully achieve work-life balance and higher profits, but he’s taught hundreds if not thousands of accountants how to do it in the UK. I met him this past summer while I was at a conference in Birmingham, England where he was one of the speakers. I knew he had a powerful message that can make a big difference in the lives (and sanity) of so many bookkeepers here in the USA. So I asked him to join me for this special 90-minute interactive session. Please come join us and see how to break the crazy out-of-balance cycle!

Have you faced these challenges yet? What have you done to get past them successfully? Please share your experiences in the comments below.


Freelance bookkeeper, trainer and consultant who works with internet savvy business owners and bookkeeping professionals to maximize cash flow and build true win-win relationships.

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6 Responses to “Where Successful Freelance Bookkeepers Get Stuck”

  • Rebecca on October 22, 2017

    Ugh, this is me! Stressful just to read this! I have already signed up for this webinar…but wondering how I am going to manage it. I have an intern…and brought in another bookkeeper to assist me in getting caught up…but it is snowballing. I have started a practice of marking out one entire day for catch-up. No calls, no emails…I don’t even look…I just work…but, alas, I only just started this so I am still struggling.

    • Gabrielle on October 22, 2017

      I can feel the stress, Rebecca! The webinar will be recorded, but I hope you can come live so you can ask for specific advice for your situation right on the webinar.

  • Cherine Mac Pherson on October 22, 2017

    I went that way by hiring staff, that didn’t work. I now subcontract work.
    I am slowly changing to workflow and automation.
    Looking forward to this webinar.

    • Gabrielle on October 22, 2017

      Thanks for sharing your path so far, Cherine. Looking forward to having you join us!

  • Joseph Blanc on October 23, 2017

    My problem right now is getting a clientel. Where do I begin. So far I have one client in which I got through a referal but referals can only get you so far. How do I market my services effectively to gain more clients ?

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