Changing Like a Kindergarten Kid

This is a busy month in my household. School begins in a couple of weeks; our oldest child starts kindergarten.

For adults, kindergarten is in the distant past, and our memories of it have faded. It’s only natural as we grow and mature.

But it’s a formative transition. It sets the stage for lifelong learning and growing. It’s an essential building block for a positive, impactful, and meaningful life.

Not unlike your first year as a freelancer.

I’ve noticed, as we prepare my daughter, that moving into kindergarten and moving into a freelance career are much alike, with similar challenges and opportunities. That’s what I’ll be writing about this week.

Kindergarten will change my daughter’s life. And if you’re going to change your life with a move from full-time employment to freelancing, it’s essential that you craft a transition plan. Freelance life is a whole new world, with different rules and expectations — just like school.

For example, both settings have new people to please.

My daughter will be pleasing her teachers. You’ll be proving that you can research or write or take pictures. You’ll be portraying yourself online in a new way; she’ll be wearing new clothes and behaving differently than she does at home.

You and your family need to be ready for change.

At the beginning of the summer, my wife and I sat down and talked about what we wanted to accomplish before school began in line with our values and goals. We talked through how this transition would affect our family. Because this is big step for all of us — both practically and emotionally — asking questions, talking it through, and building a plan served us well.

We prioritized fun this summer: trips, swimming, and play dates. But we also worked hard to get ready for school. We practiced reading and shoe tying. We bought clothes, pulled together school supplies, and figured out the school schedule.

We realized that our child and our family will shortly be living up to new expectations and structures.

The same is true for new freelancers. To some degree, the old rules and habits no longer apply. And even though it’s “your” career, your whole family will be affected.

That’s why you must be aware how your plans to leave your old work and move to new work will also impact those around you.

I think it’s really valuable to sit down and ask yourself (and your loved ones) some questions before moving forward with the freelance life:

  • What do I want my life, post-transition, to look like? Do we want to pay down the mortgage faster or visit Belize?
  • What does my family want to get out of my move to a freelance career? Does my wife want me to take the kids to gymnastics on Wednesdays?
  • What can I do now to smooth the transition? Can I find a mentor or a network or a program to help?
  • Are there essential skills I need before I start being a freelancer? How can I enlist my family to help me get those skills? Is there a program I can take to help me develop those skills?

Many of the people who are part of the AWAI family are glad to help you with these questions. Many members are established freelancers who find value in sharing what they know. Experience is key — and if you’re a beginner, it can be hard to find.

How to Write White Papers

How to Write White Papers that Command Top Fees

Marketing managers of B2B companies are desperate for good white paper writers. Get on their go-to list and start commanding thousands of dollars for a 5 to 10-page project. Learn More »


Click to Rate:
No ratings yet
Published: August 6, 2012

16 Responses to “Changing Like a Kindergarten Kid”

  1. Brian, it was good to be reminded of kindergarten, since, for me, it was a long time ago. But it gave me a better perspective of my priorities as I transition into this exciting world of freelancing.

    I am taking the Accelerated Copywriting Course; Global Freelancing Study; and have signed up for Wealthy Web Writing. I want B2B, but now I realize I need my teacher to pass me on to First Grade before I take on any more Many thanks. Dennis R.

    DennisRAugust 6, 2012 at 5:36 pm

  2. How does one start out as a freelancer? I've taken all kinds of writing classes,hold a BA in Public Relations, Speech Communications, Broadcast Journalism. I quit working 20 years ago to raise my child. She's in college now and I need to work so how do I begin in this career without having samples, a network, mentor, a client willing to take a chance on me? I will be doing Media Relations for Operation Christmas Child but that is a volunteer position. Can I get guidance please ?

    Guest (Julie)August 6, 2012 at 8:12 pm

  3. Brian:
    Great article, and a good guide to transitioning. I wish it had been around when I made the leap.
    My wife and I went freelance at the same time, but didn't fully understand or discuss the implications.
    Needless to say, it was tough as we both had to discover new work habits, new money management systems, new workplaces, and realign our personal relationship as well. Much debt and deep talks later, we're figuring it out and now it's working.

    TonyAugust 6, 2012 at 8:22 pm

  4. Hi Brian, Great analogy. I have a 2nd and 4th grader and I remember those days (and still do as we go from grade to grade). Thank you for sharing especially in reference to beginners, of which I am one. At this point in my life it's hard to grasp working as a freelancer. The hardest part to envision is that first assignment. I have been a chronic learning with little doing and desperately want to move into doing first and then learning. Look forward to reading more from you.

    Eric SAugust 6, 2012 at 11:13 pm

  5. Hi, I need some help getting started. I signed up for the wealthy web writer membership like 6 months ago but I have no idea how to get started.I am already a skilled freelance writer working for a newspaper and lifestyle magazines. How do I parlay my skills and connections into creating "the writer's life?" Specific pointers would be much appreciated.

    Guest (Patricia)August 7, 2012 at 4:59 am

  6. At what age do you recommend someone to become a copywriter? Can one do it even if they are in their sixties??

    AmynaAugust 7, 2012 at 5:18 am

  7. I so much want to become successful at business copywriting and I recently lost $648,000 in a business deal. I don't have the money to even pay for the start up costs, and IM so talented and hard working I feel frustrated. I wish I could find a way to get started......

    Guest (Kat)August 8, 2012 at 8:28 am

  8. Hi, that was a great article and excellent analogy. I am embarking on my freelance career but stuck on how to get started. It has been six years since I worked in the publishing/copywriting field but would like to start freelancing. Where can I network with others and be mentored into starting a new career?

    Guest (Lee)August 11, 2012 at 11:34 pm


Guest, Add a Comment
Please Note: Your comments will be seen by all visitors.

You are commenting as a guest. If you’re an AWAI Member, Login to myAWAI for easier commenting, email alerts, and more!

(If you don’t yet have an AWAI Member account, you can create one for free.)


This name will appear next to your comment.


Your email is required but will not be displayed.


Text only. Your comment may be trimmed if it exceeds 500 characters.

Type the Shadowed Word
Too hard to read? See a new image | Listen to the letters


Hint: The letters above appear as shadows and spell a real word. If you have trouble reading it, you can use the links to view a new image or listen to the letters being spoken.

(*all fields required)