Straddling Careers – Where Is The Tipping Point?

Where is your tipping point, asks motivational speaker Polly Pitchford?I am a wildly successful, highly sought after motivational speaker on health and wellness who has to turn down speaking gigs because my calendar is too full!

That’s my daily affirmation mantra. I’m not there yet but it’s looking better every month.

And therein lies my dilemma.

I am newly single and I have to have a full time “normal” job to pay the bills.  Before taking this current job I informed them of the speaking career I am building and gave them the 3 existing dates that I needed off.  They agreed.  Besides, I told them, I book these programs months in advance so they would have plenty of notice.  Joy upon joy, I’ve recently booked 3 more events….for this summer…not much notice…boss’ agreeable nature is thinning.

So there it is.  I’m NOT going to turn down ANY speaking opportunity and yet I’m not consistently booking enough for a secure income.  Meanwhile I can tell my boss’ “understanding” is waning.  How can I judge the tipping point? When do I make the leap?  What if I lose this job because of too many requests for days off? I feel like I'm straddling on the wings of two jumbo jets!

Believe me, I consider this a happy quandary. After all, there are a lot of people out there searching for jobs.  But a quandary it is. As the new kid on the block in this speaking business I’m reaching out to all you seasoned speakers to hear if you were ever in this situation as you were starting out in this profession. Thanks for your input!


Motivational Speaker Polly Pitchford didn’t always know the phytochemical benefits of kale, in fact, those words weren’t even in her vocabulary 30 years ago. Neither did she see any reason to do jumping jacks on a cement surface for an hour. But all it took was a chance vegetarian cooking class and some high-energy music to open her eyes upon a whole new world of healthy living. For 30 years Polly has practiced, studied, taught, educated and lived a healthy lifestyle that makes her such a powerful speaker.

Polly’s down-to-Earth and humorous approach mirrors her own lifelong journey to lasting, positive changes. The audience walks away with tangible plans for improving their health and their lives through food, fitness and fun.
To book Motivational Speaker Polly Pitchford, call 941-685-7725 or visit her at

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  1. Hi Polly.  I haven't exactly been in the same situation. But I did quit my job and jumped into this 100%. I'm not sure if I would recommend that to somebody because it was so hard and took so long to actually make money that I went into debt doing it. But here is my advice, in the hopes that you will take it as just my opinion.

    do not quit any employment until you have saved about six months worth of sustainable salary.

    you want to know that you can support yourself for at least six months while you were building this business.

    and make sure that when you make this transition, you already have many gigs booked on your calendar.


    if the current job won't allow you to take speaking gigs easily, then find another one that will. But don't quit this job until you have the other one.  I have often thought that a virtual assistant for a speaker would be a great job to have if you're trying to build your own speaking business. Because it will allow you to learn the business, give you the flexibility to take your own speaking jobs.

    any job that you can do from a computer wherever you are, would be really cool. I don't know what those jobs are, but I have heard that they exist.


    I also recommend that you post this question on the NSA Facebook page.


  2. Congrats Polly!  This is exciting!  Does this new job have vacation days for you?  When I left SkillPath to go speaking fulltime, I got one gig that paid for a full months worth of speaking events for SkillPath. (Ask Linda about her transition too, it's different for everyone).  I decided it was time to leap!  I quit thinking all I would need is one of these a month and I could maintain my lifestyle.  Well, six months later and my savings and 401K depleted I scratched by.  So, I would listen to the wise words of Kelly about having enough savings before quitting.  Also, I would ask the employer if they would consider changing you to a contract employee or a part time employee so you could still have both feet in two different places for awhile.  I love your affirmation by the way!

  3. Polly, I'm certain it feels overwhelming, and big kudos for managing it all to date. Kelly's advice is solid because this business requires you invest back into it as soon as you want to go to the next level. Websites need updating, product needs creating, etc.

    I transitioned from being home full-time with the girls to speaking so was in a very different situation. Having said that, I started on the scrappiest budget — only invested in my biz after I had earned the coin so as not to take from the family budget.

    Yes, your affirmation rocks — and made me realize why I adore you.

  4. Ah my friend, I can relate. And I think all motivational speakers truly can – to one degree or another. I absolutely love Kelly's advice too. I left SkillPath when I thought I COULD make it on my own, but then things slowed down after a couple of years and I actually thought about going back to them. Fortunately things shifted around. But – as all speakers can attest to – there are no guarantees in this business.  I would start inviting ANY and EVERYONE you can to come hear you speak. Once people find out how good you are – I believe you will start getting more referrals. I've committed to recommending you to every single women's health event I speak for. Yes, I speak on stress management and that is important to women's health, YOU speak on stress management and so much more! YOU are an expert in this field and you should be the one out there doing it!!!  I, for one, respect your dedication – and your affirmation!

  5. Polly – I'm helping a new speaker get started. I created a list of things I think a speaker needs. I'm sharing it with you, in hopes that it will help.  Except that I can't figure out how to share a PDF in this reply. Crap. Okay. I'll just put it in a blog post. Be on the lookout – it's coming soon.

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