Have you ever had to make a decision but neither of the two obvious choices felt like the right one? This happens often enough with my clients that I decided it was time for a post. Whether facing an on-the-job dilemma or a search that hasn’t yet led to the dream job, sometimes the options before us feel limiting.

Allow me to highlight two recent examples of either/or scenarios that begged the question, “What’s the third option?”

For both of my clients (note names changed for privacy), brainstorming option three made all the difference.


SCENARIO ONE: Choosing to take a job offer

I’ll begin with Tracy’s story, a “be careful what you wish for” tale. At the start of our work together, Tracy had identified a burgeoning new industry as her dream career path. After some targeted networking, she was offered a high-ranking role with a commanding salary. The challenge Tracy faced was that she had a slight case of PTSD (post-traumatic stress disorder) from a risky start-up experience that didn’t go well. Would she be jumping from the frying pan into the proverbial fire? Tracy was spinning in uncertainty and didn’t have a lot of time to make her decision. Here is some of what was buzzing in her head:

  • Would this new CEO show her true colors as the start-up CEO had and prove to be unhealthy to work for?
  • Was Tracy jeopardizing her family’s stability by choosing yet another risky start-up?
  • Given that she had already held an ample number of roles since leaving college, could she really stomach yet another potential short-term career move? How would future employers view her résumé if this turned into another short stint?
  • Could her personality handle working remotely again? She yearned for a traditional, collaborative office environment.
  • And what about the other companies she’d been talking with that mentioned they may have openings in late winter? She’d never know if one of those was the right fit if she stopped her job search.

Yet the offer in hand, technically, was her dream job. She’d said from the start that this was the role she’d wanted more than any other. She had a short amount of time to make a big decision.

During our coaching session, where we weighed all the pros and cons, I suggested that she ask the CEO if she could join in a contract capacity for six months. By starting as a contractor, Tracy would have the ability to test out the relationship with the new CEO and ascertain if they would partner well together. She could also test out another remote work environment and know for sure if her dream job was worth forgoing a face-to-face team.

The CEO was surprised that she was willing to pass up the benefits and security of full-time work but was totally okay with her starting in a contract capacity.

Tracy started the contract role just before Christmas. She can continue to vet the other companies as those opportunities do or don’t materialize and within the next six months she’ll know which direction she ultimately wants to head.


SCENARIO TWO: Facing a tough situation with a new client

In this scenario, let’s look at Sarah’s dilemma. She has an ongoing coaching arrangement. Each of our sessions involves a bit of business coaching, career coaching, and generally processing through wherever Sarah feels stuck. In a recent call, Sarah’s dilemma was that she had a really large, new client she had taken on and this client was creating both an opportunity for tremendous business growth but also stretching her resources very thin. After a trial month of servicing the new client, Sarah had determined that she was not walking away with the profit margin she needed to justify retaining the new account. But what choice did she have? She perceived her two options as either getting rid of the new account or raising her rate after only one month, neither scenario felt acceptable.

After some brainstorming, I suggested that she offer the client two service plans going forward. One included maintaining the exceptional service and higher rates she had begun with, the other offered a lower level of service, which in turn meant lower operating costs. We confirmed that there were modifications she could make that would bring the profit margin back into equilibrium should the client chose the latter option and be willing to forgo aspects of the service. The beauty of the third option was that it allowed her client to make the decision rather than Sarah having to choose for them.


When faced with a really tough decision, ask yourself if there is a third option you’re not yet seeing. By the time you’ve made it to the negotiation phase of a job offer, for example, you have more power than you may realize. Your prospective employer has decided that you’re the best fit for the company. Hiring takes time and costs money. They don’t want to begin the process with a new round of candidates. When you’re negotiating, you can present new options. If you identify something that will make an offer more attractive, suggest it. That’s completely okay. Likewise, in existing arrangements, look for ways to broaden your offerings that will benefit both parties. The world is not black and white. (My business is named greyzone for just that reason.)

The next time you’re facing a this-or-that choice, reach out. Together we can discover a third option and help you navigate your way out of the grey zone.

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