How Asking the Right Questions Saved Me From a Future in Dog-Walking

Once upon a time I was super-stupid  (no, it wasn’t yesterday! Geez. Tough crowd).

Let me set the stage:

College. Part-time job. $4K in credit card debt, racked up on essentials like cheeseburgers, XBox games, and, admittedly, textbooks. But still.

My options (as I saw them):

  • Drop out of college and go to work full time
  • Increase my hours at my part-time job
  • Ignore the whole thing and drown my fears in video games with my fraternity brothers

Or… I could look for another way.

I opted to mope around for a few days and then I asked myself the key question:

No, not “Why did this happen to me?” (I knew!)

BUT… “HOW CAN I GET OUT OF THIS? HOW COULD I PAY OFF $4K IN ONE MONTH WITHOUT INCREASING MY PART-TIME JOB OR DROPPING OUT OF SCHOOL?”

That simple shift in my thinking moved me from victim mode to problem-solving mode. I created a huge list of possible options for raising cash. After rejecting some of the less-likely entries (dog-walking and selling plasma, for instance), I narrowed the list down to eBay. I was already making a little side cash by selling on eBay, so it seemed possible.

But at the current profit of $20-$30 per sale, even I (with my rudimentary math skills) knew I was looking at a few YEARS of sales, not a month’s worth.

Then I shifted the question again:

“What could sell that would bring in big margins?” At that time, the answer was “software.” Graphic design and business software routinely sold for several hundred dollars.

So how could I buy low and sell high? Aha! I could price match software on sale at Best Buy and Staples (back when they still did this) and get it for half price, then resell it for more on eBay.

I HAD A PROBLEM. AND NOW I HAD A PLAN.

Fast-forward 30 days: Over $3K of the $4K paid off! I went from a nearly hopeless situation (“I’ll never be able to dig myself out of this hole”) to near complete success in 30 days, just by following a problem-solving system that I’ve used over and over since that time.

Maybe you have something in your life that seems impossible right now, but that doesn’t keep you from wanting (or NEEDING) it. That’s incredibly awesome. You should be congratulated because you are brave enough to want something that seems outside the realm of possibility. Go, you!

The great statesman and leader, Nelson Mandela, is credited with saying,

“IT ALWAYS SEEMS IMPOSSIBLE UNTIL IT’S DONE.”

If my story demonstrates anything, it’s that you can achieve the seemingly impossible. All you need is a process.

So the fact that you want to transition from being a customer service account rep to a VP of sales, or from a sales rep to running staffing at a non-profit, should NOT be put in the “No Way” file. In fact, at HTYC we deal in these kinds of “impossible” career changes on a regular basis (just call us fairy godpeople).

Here’s the process we use to help our coaching clients and students make “impossible” into reality:

  1. Determine the Goal. Knowing where you’re headed is critical. I knew exactly how much I needed to earn – $4K – and when I needed it (30 days). Likewise, you have to know you want to be a lab manager, or a recruiter, or a marketing and events professional before you can start taking the steps towards that goal. (If you don’t know? No worries. We can help! We have a free 8 day-course to walk you through defining your “what.”)
  2. Ask the Right Questions. Remember, it wasn’t until I put my situation in the positive (“How can I make $4K fast?”) that I moved into brainstorming mode. You have to assume that it’s possible, even if you think it’s not. For instance, you want to ask, “How could I make this happen?” not “Can I do this?” Don’t give your brain the chance to say no! Framing your question in the positive puts you in control, and it allows you to “figure out” what seems impossible one small step at a time.
  3. Generate Options. Not all my options were great ones. Walking dogs, hiring myself out as a singing telegram performer – not good. I selected the option (eBay) that provided the most chance of success because A) I had already proven it as a viable revenue generating activity and B) It didn’t require a ton of start-up capital or skill. I just needed to leverage what I was already doing.
  4. Start and Revise. In a sense, I’d already started making money on eBay. My plan wasn’t perfect, though, since my average sale was too small to make a dent in my debt quickly. I had to tweak my approach by looking at how I could accelerate my progress (by selling bigger-ticket items). On your path, you may need to revise your approach because things aren’t happening quickly enough, or because you hit a dead end. That’s part of the process! Just keep asking powerful questions (“How can I XYZ?”) and start again.
  5. Rinse and Repeat. Success rarely comes in one fell swoop. Instead, it’s a series of incremental steps. One eBay sale after another, one informational interview after another. Progress WILL happen if you keep asking the right questions!

One thing I’ve noticed after listening to hundreds of people wanting to make a career change is that often the door seems closed when they look at it head-on. They cannot see how it could possibly open, so they aren’t able to take even that very first step.

My friend and client Eric was facing a similar hopeless situation. He was working 10-14 hours a day in a soul-killing corporate environment. His dreams had him two states away, in an industry where he had no experience, getting paid more to work less. And he could NOT see how to make it happen.

But I could. I knew that he had so much to offer, so many strengths, so much valuable experience, that it was just a matter of positioning him the right way and ASKING THE RIGHT QUESTIONS. I was able to see more for his future than he could see for himself, and we created a plan of action, step-by-step, that today has him living in California where he, indeed, makes more to work less, doing activities he loves and which fit his strengths. (You can hear more about Eric’s story in this podcast episode).

If you can’t identify the path to your dream future, our HTYC career coaches are trained specifically to help you see solutions where you see solid brick walls or dead ends. We don’t do it for you; we help you see what’s possible and then allow you to get back in the driver’s seat. We teach you the process so you can save yourself – and solve your problems – over and over again, building confidence and expertise along the way.

Think career coaching might be right for you? Want an objective, trained professional to help you see possibility where you see stop signs? Please fill out this assessment form.