This week in the Opt-In: How to Have the Hard Conversation About Your Professional Future If You're Stuck

This week in the Opt-In: How to Have the Hard Conversation About Your Professional Future If You're Stuck

Finding yourself stuck in your professional journey is distressing and can often lead to a cycle of diminishing self-worth and stagnant growth. Times like these call for a "hard conversation" with your manager, bringing to light your aspirations, concerns, and the path you envision for your future at the organization. While waiting for your boss to broach the topic may seem simpler, spearheading this vital conversation can foster a more fulfilling and progressive professional life.

Obvious, right?

So often, when I share this idea, I hear people say, "But isn't my manager supposed to have that conversation with me."

Yes, if you've got a great manager. But I think you get better results (for both of you) if you take charge of the conversation yourself.

Here’s why I think you should lead the conversation:

  1. Personal Growth: Being proactive is a testimony to your commitment to personal and professional growth. It empowers you to direct the conversation towards avenues that resonate with your career aspirations.
  2. Building Trust: Initiating a candid conversation about your aspirations and concerns sets a precedent for trust and transparency, fostering a healthier work relationship with your superior.
  3. Career Advancement: By taking the reins, you open up a window to explore potential career advancement opportunities that you might be unaware of and can collaboratively work on a plan to achieve them.
  4. Confidence Creation: Approaching the meeting with confidence builds your self-assurance and cultivates confidence in your superior about your envisioned future. It’s a chance to demonstrate your initiative and potential, thereby building trust in your capabilities.
  5. Job Satisfaction: Leading a dialogue focused on finding solutions to the issues that have been hindering your growth can significantly enhance job satisfaction, paving a clearer and more aligned path forward.

Ready to put a meeting on your boss's calendar?

Before you reach out, ponder over these essential questions:

  1. Why Do You Feel Stuck? Is it a missing sense of adventure, an unclear pathway to the future, or a diminishing sense of belonging in your team? Delve deep to understand the root of your discontent.
  2. What Kind of Person Are You Talking To? Discern the nature of your superior — are they a coach nurturing your growth, a patron facilitating your journey, or an investor focused on outcomes? Tailoring your approach based on their disposition can be a game-changer.
  3. How Do You Usually Have These Types of Conversations with The Person? Reflect on the dynamics of your previous conversations. It's vital to communicate your concerns without causing undue alarm, maintaining a tone that is both respectful and assertive.

How are you feeling right now? Empowered or a bit freaked out? Did my questions help you think through how to have this conversation, or do you wish I'd given you more?

I can give you more. Really.

An entire toolkit that includes everything I just described, created just for you. I shit you not.

So, we developed that different something. It’s a solution that flips the script. It places you, the employee, at the heart of your own professional journey.

Say hello to the Inspire Transformation Guide .


I partnered with the brilliant Dr. Sherry Woosley and the team at Macmillan Learning to create the Inspire Transformation Guide. It's built on an employee experience survey they built, tested, and validated from the ground up. Their research-backed approach + my "How to have the hard conversation" and we've made something magic.

How it works is simple:

  1. You purchase ($9.95) and complete the assessment.
  2. We send you a custom report with personalized results and a made-for-you toolkit of resources on starting the conversation with your manager about your future. There’s even an option to add a private coaching session. And we've even made it so you can have your conversation with a mentor or coach. YOU get to choose.
  3. You start the process, and the magic conversations start to happen.

Isn't your future worth the investment? I think it is.

You can learn more and purchase on our website starting now .

There’s one catch: this offer will only be available until Friday, October 6. Act fast. Don’t be scared. Dream big.

PS. There's also an option to upgrade and book a 30-minute one-on-one with me at super-discounted rates.


Have a question for me? Shoot me a DM

Want more from me? I'm posting daily on LinkedIn.

Here's what you missed this week:


  • One of my clients got some excellent news. And now she's terrified. FYI, this is a totally normal reaction. See what I had to say.
  • Do you like to be a Naval officer or a Pirate, or somewhere in between?
  • What did your mentor do for you? I wondered how people measured great mentorship. Not surprisingly, people had lots of different answers.


Want help navigating the future?


A Potentialist, author, and Edutainer, I dedicate my time to unraveling the motivations behind individuals' choices about the future. People can't create the future if they're fearful of it.


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