Should You Kill Your Darling?

Scroll down ↓

Seriously, she said, you want me to kill the thing I’ve nearly died to create?!


It was a conversation I’d had before, and I will have again.

Look, she said, I’ve been at this for five years. I’ve developed programs and products. I’ve built a brand. I’ve paid people to help me build it. I have a serious community. I’ve written more than 100,000 words of content. I’ve built a list. I’ve given up nearly everything to get here.

I’ve dropped tens of thousands of dollars into making it work. And walked away from so many other opportunities that would’ve been worth tons more. The opportunity cost, alone, is likely in the hundreds of thousands.

Oh, and this thing you’re telling me to kill, it’s working. I’m making money. And, by all accounts, I’m making a difference.

Then, what’s the problem? I asked.

I’ll tell you the problem, she replied…it’s fucking killing me.

And I hate going in to work at the company I’ve created.

Sure, it’s making a bit of money, but I honestly couldn’t care less about it. I thought I’d feel differently once I’d “made” it. But, I don’t. And, if I’m really being honest, it’s not doing anywhere near what I thought it would. It’s not giving me the money I need, it’s not really catching on or making the difference I thought it would and I really, really don’t like the work.

Again, I ask, so what’s the problem?

Can’t you see, I’ve given up five years of my life to make it work, tons of money, most of my friends. I can’t just walk away when I’ve invested so much, given up so much.

If I do that now, it’d all be for nothing.

And if you don’t? I asked.


Two roads, I offer.

One road is the path of blind allegiance to the past.

It’s sticking with the living you’ve built out of attachment and shame.

Attachment to the need to feel what you’ve given up was “worth it.” Attachment to need to feel you haven’t “wasted” the last five years. Attachment to the ethos that’s been burned into your psyche that says “I’m the type of person who finishes what they start, even if it kills me.”

And, the shame or judgment you feel will touch down in your life, should you own the fact that it failed to become what you’d hoped and walk away.

So, you stick with it, continue to give up even more of your life, money, friends and health. Not because you’re doing the thing you can’t not do. Not because it will ever give you what you need. But, because…

You let your decisions be guided too much by what’s in your rear-view mirror, rather than your front windshield.

Doesn’t matter if you’re an entrepreneur or you’re a lawyer or doctor and you’re talking about a six-figure education, venture capital and time spent building your business.

Either way…

You’ve become a prisoner to your sunk costs.

The second road starts by wiping the slate clean. But, not really.

You walk away from everything you’ve invested. Your money, your time, your sacrifice and suffering. You realize, though, that walking away doesn’t mean “it was all for nothing.”

You’re not really walking away, that’s just the voice of shame speaking. What you’re really doing is reframing the cost. Viewing the entire thing—the money, the time, the energy, the sacrifice—as the price of your “continuing education.” One that can only be forsaken by leaving it unexamined and untapped. And you have complete control over that decision.

So, you examine it. You tap it.

You integrate what you’ve learned, and then let this wisdom guide your decisions from this moment forward.

You ask yourself:

Knowing what I know today, would I start the same venture or career?

You find yourself answering a clear and resounding no. So, you kill your current business. Or you sell it, or find someone to run it who does love it. You decide to begin the process of transitioning into the path that willow allow your best self and, along with it, your best life, to emerge.

You take the short-term hit to your ego and emotional bank account, then put all you’ve got into crafting a more-informed future. Sure, there’s a short window of shame and even judgment.

But, the joy and excitement created by the freedom to now build something you’re truly drawn to, something that’s actually working on a level the old business never did or could, lets you leave those feelings in the rear view mirror with ease.

And, the judgment you thought would come your way?

Well, it does. But like most of us realize…

The world is far less interested in us than we perceive it to be.

People move on and when those same people who judged you see you flourishing, somehow you magically make the shift in their eyes from loser to lunch-pal.

Question is, which road will you choose?

The one that binds or the one that frees?


When you allow sunk costs to become your religion, you end up with a sunk life.

Learn from what got you here, but live into what will get you there.

Join our Email List for Weekly Updates

And join this amazing community of makers and doers. You know you wanna...

15 responses

15 responses to “Should You Kill Your Darling?”

  1. Bill says:

    What if your 6 figure income also comes with 6 figure debt (primarily student loan)…on top of high monthly expenses and 4 mouths to feed? Living paycheck to paycheck on 6 figures is very challenging. How does one start over with a clean slate in this situation? I’d love to but don’t know if I can. #helpabrotherout

    • Ginger says:

      I strongly recommend picking up one of Dave Ramsey’s books. His financial advice is sound and he’s all about helping people exactly like you get on top of this and get their lives back. You can beat this, you really can.

    • Dave says:

      If you’ve never read his stuff before, Mr. Money Mustache has some good ideas about paring down expenses and living a simpler life. Check out his blog.

  2. LxoJ says:

    Timing is everything. Yesterday morning at 3am I awoke and put into the play of *killing* a 2-year on-the-side passion project Artist2Artist Stitcher podcast and companion column series. What seemed like a good idea at the time had slowly taken me away from my main love and focus on my own musical artistry and band.

    The creativity, time & effort I had pumped into the podcast/column with its monthly deadline and growing affection of and interest from musical artists & publicists was one-sided. Everyone in the industry saw me as *flourishing* — I was going into default financially and morecritically, energy-inspirationally.

    In this region of the country the act of stopping something in which we feel we are extremely invested is: “cut bait and fish.”

    Yesterday for me it was just “cut bait.” I don’t need to fish for a while.

    Love your stuff, Jonathan.



  3. Mitchel says:

    This message resonates loudly with my soul. My family started on a journey of simplicity and continue to evolve as we fine tune or purpose.

    I’m one of those doctors you mention above who walked away from a busy practice to live a different life. I still practice but on a completely different scale and entirely different manner.

    Shrugging off the expectations and perceptions of others is a challenging part of the process but so critical to success.

    • Jason says:

      Congratulations, Mitchel! It takes courage to walk away. Many could learn from your story. Best wishes on your freedom journey!

    • Jonathan Fields says:

      Thanks so much for sharing this and reminding us all that this is not just about entrepreneurs, it’s about any career and really most parts of life.

  4. A powerful message at just the right time. Thank you Jonathan. I woke up a few weeks ago and shook my head. I spent the last year reinventing myself and my business and I had this lurking feeling that something STILL wasn’t right. Something STILL needs to die.

    I share this because I’m realizing it’s not always the WHOLE thing… this time around I could see and feel that I was about 3 degrees off – not 180 degrees off… but those 3 degrees were still eating at me. I’m taking the week to sort through what needs to be adjusted, and what needs to die.

    Thank you for the timely reminder.


  5. Jonathon I am a longtime lurker though I share your work all the time. Thank you FOR THIS piece of work. These words are speaking so LOUDLY to me right now I just had to comment

    • Jonathan Fields says:

      So glad it resonated AND even happier to welcome your voice to the conversation. 🙂

  6. A good reminder that letting go is okay.

    Your question reminds me of a book used as a text book in a social psychology course in grad school. It was called “Too much invested to quit” (by Allan Teiger) and used the analogy of having put money into having a car for repairs over and again to the point that one thinks one has too much invested to be able to get rid of it, and compared it with relationship issues.

    I sometimes ask people to imagine that nothing changes, and ask them if they still want to be there in 5, 10 or 15 years. If their answer is “no” then why are they staying now?

    • Gertrude says:

      Thank you Jason for the article and Diana for your comment. The question about nothing changing resonated with me. This whole article not only speaks to businesses, but also relationships and life in general.

  7. This is a good question and lesson for all to question throughout ones life. There’s a saying, “If you’re tired of starting over, stop giving up.” Or something along those lines. That said, I lived a business that was all consuming throughout the 90’s & half of 2000 until I sold to my employees in ’05. Money wasn’t the issue as the business was extremely profitable.

    It was difficult but my life was in turmoil and deeply unhappy. I attempted to save my marriage following but failed. I took two years to right the ship before even thinking about going back to work.

    In Jan of ’08 I started back as I was replenished and excited to get back in the business fray. In March I was diagnosed with stage III lung cancer (non smoker). Stress is what I attribute as the doc’s stated I’d probably had it 2 years prior to diagnosis.

    I cannot stress enough to all the power stress plays on ones life. I was a complete case and filled to the brim with it. The good news is, the cancer diagnosis opened my eyes to what is really important in life and to focus on such. Too much to list her but if you’re interested, I wrote a book on it titled, “It’s an Extraordinary Life – Don’t Miss It”. Avail on Amazon or my site…

    This is not a plug for my book. Just wanted whomever on this thread cares to contemplate, I had to learn this aspect of life by paying high dividends. I probably wouldn’t change much but now that I know what price anxiety and discomfort plays, I have changed those aspects of my life 180 degrees.

    I was told I had one, two years tops to live following my diagnosis. Clearly they were wrong. The only thing I can attribute is changing the way I approach living.

    Hope some thread of this experience helps…

  8. Mary Jane says:

    An old boyfriend and writer first introduced me to this phrase. This post just inspired me to trash the idea I was finalizing TODAY. I am now realigned with the passionate me hiding right under the “I should be impressive” me. I am so happy and so thankful, Jonathan. My intuition rippled when I saw your email–now I know why. A tap dancer is finally born~!!!