Everyone goes through a messy middle. It's the universe's way of testing your merit. Do you really want this and how badly? Prove it. 

The "messy middle" is a universal experience. Whether it's a job search, a relationship, or starting a business, this phase is characterized by self-doubt and questioning. But instead of being a test of merit, it's an opportunity for introspection and growth.

It is either the space where desperation or inspiration is born. Do you you sacrifice your authenticity to become what you think the company wants or do you define what success looks like to you and go after it with everything you have?

What the Messy Middle Looks Like

• When I talk with an executive and they immediately go into resume, LinkedIn, and tactical things, I will almost always disqualify them immediately. This happens weekly, so selfishly, I’m hoping this article will save me some time. 

  
  

  If you’re focused on the past, how can you possibly see where you’re going? If you want an answer for every possible question the hiring manager could ask, how can you possibly be actively listening? If you’re taking calls desperately trying to prove your value, you’ve already lost.

  Focusing solely on tactics like resumes and past accomplishments during the messy middle is a trap. It conveys a lack of direction and prevents genuine connection.

  • Losing Focus: Obsessing over the past hinders future vision.

  • Forced Authenticity: Desperation can lead to inauthentic behavior during job interviews or relationships.

  • Seeking Validation: Begging for opportunities through constant calls demonstrates a lack of value.

  This pattern creates a vicious cycle – desperation leads to poor choices, ultimately disqualifying you for the things you truly desire.

  People like to ask for templates, tracking docs, and common interview questions. Do I have these things? Of course. Do you really want to spend our time together going over what everyone else has access to? 

  Think differently. 

How to navigate the messy middle

Values. When I tell people they need to have a clear understanding of their professional values and their energy drivers, I’m often met with pushback. I hear something along the lines “I already know all of this,” or “I’ve already done a lot of work in this area.”

Let me be clear, knowing and understanding are two very different things. Knowing your values but not understanding how to position them throughout the interview process will lead you to ultimately sacrificing your values. You’ll set yourself up to lose not just the negotiation but sometimes the opportunity itself. You will end up with more of the same.

You know what’s boring? A laundry list of accomplishments an executive has achieved in the past. No matter how impressive.

You know what stands out? Speaking to your values, how you work best, how you are set up for success, and how you won’t sacrifice your integrity for a paycheck. 

And guess what? The more honest you are through this process the more likely you and the company are going to be successful moving forward. 

Once you have a clear understanding of your values and know how to use them to your advantage, develop your personal board of advisors. This is not your best friend and significant other. They are important but often too close to be objective. 

You need a strong group of 4-7 executives who you meet with weekly or regularly. These are people you look up to. They are people who are going to challenge you. They are not always your peers. Set clear expectations with them and have them hold you accountable.

Lastly, shut up. 

You have two ears and one mouth for a reason. No one has all the answers, not even you my friend. Actively listen and gather information before you jump to a response. And if you don’t know the answer, that’s okay! 

Would you be offended by someone who said something like, “that’s a great question and I know I have an answer for you but I’d like a little more information before I respond. Can you tell me a little more about X?” 

I’ve had clients follow up interviews with emails answering questions more robustly. Guess what, they often get the job. 

Change the way you look at the messy middle

If you look at finding your next opportunity as “chewing glass”, then that’s exactly what you’ll get. If you instead look at finding your next opportunity as a way to explore what you really want and what’s best for you and your family, you’re already ahead of the pack. If you keep your values at the front of your positioning, you won’t sacrifice them. 

It’s easy to be all in when your values are aligned. And if you lose an opportunity because your values don’t align, I’d say you dodged a bullet. 

In short, know yourself, build a support system, and get out of your own way. In the messy middle, you create and creativity has little to no structure. Without creativity, you end up with more of the same. So embrace the messy middle with childlike curiosity and buckle up.