How To Conquer Deal Fatigue To Unlock Your Deep Wealth

Jeffrey Feldberg
4 min readFeb 15, 2024

Deal fatigue is a factor that stands between you unlocking your well deserved success, or not. Worse yet, deal fatigue can prevent you from achieving financial freedom in your liquidity event. Jeffrey Feldberg, a 9-figure post-exit entrepreneur, shares proven strategies from the trenches to help prevent and overcome deal fatigue.

There are situations when you feel mentally or physically worn out from business negotiations. You just want to wrap things up quickly, satisfying yourself with “it’s good enough” or worse, decide to abort a promising deal because it seems “too stressful”.

During negotiation processes for any deal, whether personal or business-related, you may often find yourself exhausted, physically or mentally, or even both. This fatigue might lead you to settle for less than you deserve or make a decision that you might regret. In the world of deal-making, this is referred to as deal fatigue.

Deal fatigue often manifests when you start making concessions that you wouldn’t have considered at the beginning of the negotiations. It could be because you’re mentally exhausted and just want to move on from the deal, or simply because you’ve been worn down by the negotiation process.

There’s a high chance that you may have experienced deal fatigue at some point, even if you don’t realize it. After agreeing to certain prices or conditions, you may find yourself wondering why you made such a decision. Or, sometimes, after the deal’s conclusion, you question its appropriateness or success.

Today’s business landscape inevitably brings about the potential for deal fatigue. Whether it’s in the tension-filled conference rooms of investment bankers or the seemingly endless back and forth exchange of M&A legalities, deal fatigue can sneak up on even the best of us, leading to poor decisions and missed opportunities. To protect yourself and your business, we need to develop an effective road-map to overcome these hurdles.

5 Key Strategies to Deal with Deal Fatigue

To help you steer clear of the hazardous business fog known as deal fatigue, here are five key strategies to guide you:

  1. Preparation: preparation equips you with foresight. Understand the terrain before delving in. Identify your deal points (what you want) and your no-fly zones (what you’re unwilling to compromise on). This step gives you clarity, eliminates indecisiveness, and demonstrates to the other side that you are prepared and professional. Preparing in advance is key to any good deal and will keep you well anchored when the inevitable fatigue sets in. Knowing clearly what you want (deal points) and what you don’t want (no fly zones) in advance, sets the parameters for negotiations. This clarity refines your focus, helps avoid unnecessary delays, and portrays you as a professional negotiator, thereby saving everyone time and hassle.
  2. Recognize Self-Talk Lies: In deal fatigue, you tend to justify questionable decisions to yourself. This self-deception is what’s referred to as “self-talk lies.” Investigate what these lies might look like for you and share them with your team. This prepares your team to help you take a step back when you’re spiraling into the fatigued decision-making zone. Understanding the narratives you tell yourself during deal-making is crucial. Oftentimes, fatigue causes us to negotiate with ourselves, questioning our stands or offering justifications for lower than expected outcomes. Be honest about these conversations. Let your team in on your self-talk so they can help you stay on track when fatigue occurs.
  3. Recognize Buyer Tactics: Be aware that some buyers may intentionally try to wear you out. Tactics could include delays, constant requests for reports, and last-minute conditions. Being aware of these tactics can help you counteract them and cut deal fatigue off at the pass.
    Every negotiation has its set of tactics. Buyers may induce deal fatigue by intentionally slowing things down, loading you with irrelevant requests, or launching into rapid-fire decisions that can wear you down. Recognizing these tactics can help you call out unnecessary delays and keep you from getting worn down.
  4. Create Realistic Projections: Projecting beyond your capabilities can lead to more exhaustion and deal fatigue. Ensure the projections you provide are feasible and aimed at meeting or exceeding your targets. Maintaining credibility is paramount in any deal-making process. Ensure that all projections you provide are accurate and attainable. Over-promising and under-delivering can be a trigger for deal fatigue as you scramble to justify the discrepancies.
  5. Assemble the Dream Team: Surround yourself with experienced advisors and subject matter experts. This dream team’s purpose is to handle the complexities of the deal, keep you from deal fatigue, and ultimately safeguard the best interest of your business. Your negotiation team, both internal (key employees) and external (M&A advisors, lawyers, tax strategists), can serve as your shield against deal fatigue. Choosing the right advisors not only relieves you of much of the negotiations but also adds a layer of expert perspective to your tactics. Remember the words of Maxwell Maltz, “When the team works, the dream works.”

Wrapping Up

Deal fatigue can sneak up on you and lead you into making regrettable business decisions. With these five strategies, you can better anticipate, manage, and prevent yourself from falling into the debilitating trap of deal fatigue. In the end, remember that your wealth isn’t just about the figures, it’s about the depth of your journey and the impact you create. Continue to thrive and prosper while remaining alert and steadfast against deal fatigue.

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Jeffrey Feldberg

Helping you capture the best deal on your exit through the Deep Wealth 9-step roadmap. Leverage the same strategies I created for my 9-figure liquidity event.