What is a Reasonable Length of Time to Put Your Career On-hold to Create a New Career Future for Yourself?

How much time should I give myself to re-boot my career or to re-position and re-brand my self-employment consulting or coaching business?

THE REAL DEAL Live Q&A Show* (Introduction / Episode 1) — Accompanying video to blog article: “What is a Reasonable Length of Time to Put Your Career On-hold to Create a New Career Future for Yourself?” Alternatively, play the accompanying video for this article on Facebook: https://www.facebook.com/GreatFutureNow/videos/1592658357459314/

What I am doing right now — and I am leading others to do with me

Welcome to the culminating stage of a long journey for me. Or, put another way: Thank you for joining me as I launch my next, best-ever venture yet! One way of looking at “this venture” for me is: THIS is THE ONE that will be my vision/mission for my life’s work until I perish from this mortal coil. (Well, this one, and another two or three tightly-aligned ventures too, that will coincide and converge elegantly with this one.)

What’s really going on here? I am not actually “starting another” career. I am actually letting-go of past vestiges of my consulting projects and clients, focusing powerfully on providing coaching and being a Coach, and re-branding my coaching services. This will also allow me to grow anew a sideline profit-venture related to coaching and breathe life into a non-profit venture organization that inspires me to take-on inviting others to help me Save the World! (Just kidding, sorta. The non-profit organization is already shaping-up to be a huge audacious game though!)

To take-on your own journey/adventure, come along with me for my venture, and allow me to support and facilitate you along the way, please be sure to read the, “My (not-so) private and personal journey…,” section at the end of this article.

A brief backstory: What it took to get here, what I discovered, and where I stand now

A few years ago I lost an appropriate, even somewhat sexy, job as a leader at a web media design and technology company. I had a corner office on the thirteenth floor with floor to ceiling windows in a downtown office with all-weekend access to downtown parking and a mini-bar in my office.

A corner-office on the 13th floor… You’ve “made it!” Right?

Kinda cool, right?

It seems that every few years, I would leave my self-employment consulting and coaching practice to try-out going into business with someone else who wanted to hire me to help them make a big deal out of his business. So, I would bring my entrepreneurial spirit, consulting savvy, and coaching/leadership acumen to the cause of someone else’s venture. What was in it for me was: all the building-blocks were bought and paid for, laid, and ready to be leveraged; and I could have instant companionship and collaboration in venturing in business, something for which I have long been passionate. The owner will tell you, he laid me off. I’ll take responsibility to say that I didn’t give him much choice.

Your fervent misguided sense of entitlement is stunning

When I was due to be acknowledged for a couple of years of sacrifice of long hours and devotion to the cause of the business and its owner and I was due to receive a long-awaited salary-raise, rather I was laid-off, permanently. That being said, I was undoubtedly coming-off entitled and I sometimes treated the owner like I knew better what was good for the employees and his business than he did. That’s all water under the bridge and nothing more than a story now.

(I have come to learn about myself: “That’s how I get” when I engage in an Employment Role, “working for somebody else.” That’s NOT authentically who I really I am. When I compromise being true to myself, I end-up with latent resentment that manifests as I am “entitled to have things go *my* way.”)

Since then, for a couple of years, I’ve been working sometimes and generating income sometimes, and also some of the time not working in a way that generated not much income at all. Also perhaps not working “hard enough” at “making a living” enough of the time to satisfy some of the people in my life who share their convictions that it’s all about bringing in a paycheck, paying the bills, how it looks, and/or survival. Do these expectations sound familiar to you? Of course they do. Are they your expectations of yourself, and/or others’ expectations of you?

During these past few years, it seems that I have been pausing quite often and for extended periods — seemingly sometimes weeks at a time — to assess and evaluate my values and the filters I use to look-at, interpret, and relate-to the world. To the consternation of those around me, it’s as if I am not fulfilling on normality to work and produce and achieve and collect-and-spend money according to expectations about the behavior of a sane rational modern citizen. I discovered that the expectations of others had become embedded within my own values and filters; and when I’m not paying attention, I feel like the expectations of others *should* also be believed-in as my own expectations.

As a counter-move to that discovery about myself, I took a deep dive within my psyche and spirit to build awareness about and consider and feel my way-through an exploration of “what matters to Me.” Also I have a craving to reinvent my life and reinvent my Self. That’s just me. Does that sound familiar to you too? All the while though, and here’s the rub, I carry with me this nagging feeling that “this is taking *too* long!”

Then it hits me! We’re talking about “a few years” here in comparison to the 45 years that came before bringing me to and leaving me where I found myself — dissatisfied and some days even disgusted with living and working for a worklife and a lifestyle that I know is not authentic for me. Sometimes I wondered, if that way of living is really authentic for any human being — and s/he just don’t realize it yet.

For now though this is my work for myself, my worklife (or, “My Life’s Work”), and my lifestyle; and so I’m not going to endeavor to roll-out an imprint for living onto anyone else. I’m going to acknowledge this though: If it’s taking me a few years to explore and discover and reinvent myself and my life and career relative to the 45 years that came before, then I say, “Gimme a break!” to anybody who thinks that this investment of self-centric research and development has been any sort of “waste of time.”

What it looks like to “take-on my coaching career anew,” and what there is for which I will be responsible

So what does it look like? What is there to do? When an experienced, expert Coach and Consultant reboots his career and re-brands his services?

What my game of “My Coaching Career Anew “ looks like for me:

For me, I am practicing hour-by-hour, day-by-day, being, what I refer to as, Being True to Myself. Because I know that: The less often I am True to Myself, the more fatigued, disillusioned, and withdrawn I become. Also, the more True to Myself that I am, the greater my inclination and capacity for Being Empowered and Graceful for anything and everything.

What I will be taking-on on a daily, weekly, and/or monthly basis is no less than…

A Basic Everyday To-do List of Action Items for the Self-employed Sole-proprietor, Consultant or Coach

  • Prep for today’s CALENDAR events: Client meetings, Sales events, Marketing and Promotion events, Networking events, Co-working and/or Collaboration meetings, Self- and/or Business-development events and conferences, personal care events, family events, community and volunteerism events
  • Incoming VOICEMAIL and SMS review and replies
  • Incoming EMAIL review and replies: Employ “Getting Things Done (GTD)”© methods
  • Today’s IDEA for BLOG post & VIDEO broadcast
  • Review ONE-OFF Action Items ― Act, Defer, Delegate or Delete
  • Promote upcoming CALENDAR-scheduled EVENTS (and CAMPAIGNS)
  • Promote SERVICES: Sales, Marketing, Other “Get Clients Now”© strategies
  • Set-up New EVENT(S)
  • New PROJECTS collaborating & scheduling: Planning for Events, Campaigns, Development, Networking, and Prospecting
  • New PROJECTS R&D: New/re-branded website; better tech/Web-online tools; social media; etc.
  • PERSONAL Administration
  • BUSINESS Administration: Accounts RECEIVABLES, Accounts PAYABLES due this and next week, BOOKKEEPING
  • BUSINESS Administration: IRS, TAXES, and FEES information and forms due this and next week
  • BUSINESS Administration: ACCOUNTS’ UPDATES and LICENSURE, and RENEWALS due this and next week

In case you are wondering, here a few ways I practice living in the moment each day while I play this game of “working-from-home, business rebooting, My Worklife My Way”:

My Beingness

My Gracefulness and Empowerment is sourced by my practice of Being True to Myself.

My Landscape (What it looks, sounds, and smells like according to my likes)

My ‘Walls of Gratitude’ surround me in my home office
  • My ‘Walls of Gratitude’ surround me in my home office (a collection of cards and notes from cherished clients, friends, and family, as well as, the occasional inspirational meme or bauble),
  • Funk Jazz, mellifluous piano, or acoustic guitar playing,
  • lots of water drinking,
  • hot tea sometimes,
  • high-caliber candles with perky or soothing aromas,
  • frequent video calls and conferences with partners, prospects and clients,
  • periodic out-of-the-office co-working with partners, client meeting, and business-to-business (B2B) networking events for networking, presentations, and learning/R&D.

About practicing Being True to Myself

To be open and transparent, the complete Real Me with you. I want to really share how life goes for me while I am taking-on a new venture (i.e., next most-risky entrepreneurial phase) in my life. Even though I am practiced and expert when coaching to my clients and my own personal practices empower me to walk-my-talk in my own life as a world-class coach, I am also a world-class human (iteration beyond ‘cave man’) being. I am human. So, despite my successes along the way and my talents that empower me to be an amazing Coach for my clients, I have failed at more games in business and life than I have won. The perseverance to keep coming back again for yet another swing at-bat is what it takes to achieve extraordinary home run plays! “Did you see that?! I can’t believe I hit it out of the ballpark like that!”

The perseverance to keep coming back again for yet another swing at-bat is what it takes to achieve extraordinary home run plays!

Another aspect of my human nature with which I distinguish what’s so and then take it on is: Sometimes I say one thing, and then I discover that I have done other than what I said I would do. Very modern homo sapien of me. You too, I’ll bet. I practice Living Authentic by often distinguishing where I auto-human-matically show up as “inauthentic,” i.e., not being true to myself, not being fully self-expressed, not being real about the here and now, and/or being a hypocrite.

One profound example of me doing my very best version of “an inauthentic human being” is that I don’t always share those in my life about when I am falling down, losing ground, or not winning the small games that are at-play inside of the big games at-stake in my ventures. I don’t want to have or create an experience with others that “I am struggling” or “I am lost a game today.” I hide the truth when it is difficult, and I talk-up what’s going-on when I can look good as a player in my stories! When I am not paying attention, Greg can be very human indeed. I am glad that I am practiced at noticing when this may happen, and so I often steer clear of being “that guy.” (Except for when I don’t.)

What my Game of My Coaching Career Anew LOOKS LIKE FOR OTHERS around me

Well, to follow-through on my “inauthentic way of being” previously mentioned, I acknowledge that, when I do not share with others that I am dealing with challenges, then they don’t really know me, know what’s going with me, get to love me, get to express their love for me, or get to support me when I could use it most. Also, they get a sense of me withholding from them or they may even experience me as fake… I mean, really, how can anyone always be winning and never losing? (Does that sound like some Facebook feeds you follow?)

My (not-so) private and personal journey to reboot my career and re-brand my coaching services

An Invitation for You to Join a Career Reboot/Business Re-brand (Uniquely Private and Exclusive) Mastermind-Cowork Team Led by Achievement Coach Greg Kilgore [Fall 2017]

WHAT I WILL SHARE PUBLICLY: Blog posts and accompanying videos, like this one, about the journey and process — good, bad, ugly, trials, and troubles.

I INVITE YOU TO GET PERSONAL WITH ME, as well as, professional with me… You are invited to a private, exclusive program with me: Contact me to join my private, exclusive Career Reboot/Business Re-brand Mastermind-Cowork Team for starting-up, rebooting, and/or transitioning your own business and/or careerThe price for this program is as low a price as I will ever offer — because I am not only going to your Coach and Group Leader, but I am also going to give myself the elbow-room to be a full-fledged participant in the group too.

To join this Mastermind-Cowork Team, please call me: (407) 796–9362

■ Discover & Re-invent yourself… Achieve your Authentic Self… Live Your Great Future Now!
BOOK NOW for Private Coaching, Team Coaching, or Event Engagements at GreatFutureNowCoaching.com
■ Featuring ACHIEVEMENT COACH GREG KILGORE ■ (407) 796–8362


Achievement Coach Greg Kilgore leads GREAT FUTURE NOW…


Achievement Coach Greg Kilgore leads GREAT FUTURE NOW Coaching for Breakthrough Performance, Transformative Achievement, and Empowering Leadership • 407.796.8362 • GreatFutureNowCoaching.com

Achievement Coach Greg Kilgore

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Coaching for Breakthrough Performance, Transformative Achievement, and Empowering Leadership • 407.796.8362 • GreatFutureNowCoaching.com


Achievement Coach Greg Kilgore leads GREAT FUTURE NOW Coaching for Breakthrough Performance, Transformative Achievement, and Empowering Leadership • 407.796.8362 • GreatFutureNowCoaching.com