The Achievers Dilemma: Why High Performers are never content

High achievers often face ongoing shame and guilt from feeling like they are never doing enough. 

No matter how much they do or achieve, it never feels like enough.  

This is called The Achiever’s Dilemma, and it’s something I’ve struggled with for many years. 

While I strongly believe that intrinsic drive to succeed is a blessing not a curse, this can have many negative effects. 

These include constantly thinking about work, being less present with loved ones, and having difficulty transitioning to home life after a long day. 

I’ve worked very hard to address these challenges over the past 6 years, and while I’m still FAR from perfect, I wanted to share my top 5 strategies to help if you are struggling with this. 

1. Set clear boundaries for work. 

Work expands to fill the time allotted, so if you have a clear start time and end time it can often force you to prioritize and work more efficiently. 

For me it’s 8-6 M-F, with a one hour lunch break with my wife and toddler. 

2. Set clear goals every quarter and clearly define the activities you need to focus on to achieve those goals. I use a system called the 12 week year for this process. 

3. Say NO or DELEGATE any activities which are not aligned with your goals. 

People pleasing is a major culprit of poor time management. 

So is shiny object syndrome, or chasing whatever the latest and greatest thing is. 

So is giving into distractions.

And content consumption. 

The list goes on and on. 

We only have so much time in the day, and valuing your time starts with learning to SAY NO. 

Always make the MAIN THING the MAIN THING

4. Prioritize Self Care. 

As a High Achiever, it’s very easy to always make work the top priority at the expense of your health. 

Making time for exercise, meditation, faith, and family connection actually leads to more productive, focused work. 

So these activities get prioritized on the calendar just like any important meeting would. 

Same thing goes for coaching and mentorship. 

No matter how busy I am, I always ensure that I have a coach to keep me grounded and focused. 

5. Give yourself GRACE. 

Perhaps most importantly, we must accept that we are not perfect and will never have a perfect day. So if you waste time, get distracted, or work on a lower priority item than what you originally intended to do, FORGIVE YOURSELF. 

We are all simply humans doing our best. 

God’s grace lets us conquer a multitude of flaws, and we must extend that same grace to ourselves on a daily basis.


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