by rshafir | September 11, 2025 | Uncategorized
When Overthinking Becomes the Enemy of Progress
Eli sat in front of his laptop, staring at a nearly finished proposal for a potential client. He’d been at it for hours—tweaking a phrase here, shifting the layout there, rewriting sentences that were fine the first time. The funny part? The client wasn’t paying him for perfect grammar or a flawless design. They wanted his creative approach to a problem. But Eli had hooked onto a detail loop, and now he was at risk of missing the submission deadline altogether.
Sound familiar?
For many entrepreneurs, overthinking and perfectionism are invisible productivity killers. While hustle culture glorifies “sweating the details,” in practice, circling endlessly around the same project prevents you from moving forward. You’re not bouncing between opportunities—you’re polishing, stalling, and second-guessing.
Why Entrepreneurs Overthink
Running a business is high-stakes, and when the stakes feel high, the brain defaults to caution. Overthinking becomes a defense mechanism: “If I just polish this idea a little more, I’ll protect myself from criticism.”
But here’s the trap: the more time spent overthinking, the less time you spend testing, learning, and iterating in the real world. That’s where growth happens.
Harvard Business Review once noted that perfectionism can masquerade as a strength but actually leads to procrastination and stress (HBR article on perfectionism). For founders and leaders, that stress gets compounded when it stalls momentum.
Perfectionism in Disguise
Sometimes overthinking doesn’t look like perfectionism at all. It can show up as:
- Never sending the email because you’re waiting for the “perfect” wording.
- Redesigning your website for the third time instead of launching your service.
- Over-researching every possible outcome before making a decision.
The cruel irony is that clients, investors, or customers often value speed and authenticity over spotless execution. In fact, LinkedIn’s founder Reid Hoffman famously said, “If you are not embarrassed by the first version of your product, you’ve launched too late.”
The Overthinker’s Survival Guide
Overthinking feels productive, but it’s really disguised procrastination. Here’s how to break the cycle:
- Set a Deadline for Decisions
Give yourself a specific time frame: “I’ll polish this for 30 minutes, then it’s done.” - Redefine “Done”
Done doesn’t mean flawless—it means ready for feedback, testing, or launch. - Shrink the Task
Break a project into smaller pieces so you can ship something quickly instead of stalling on the whole thing. - Use External Accountability
Tell a colleague, coach, or friend when you’ll hit “send.” Accountability creates momentum. - Interrupt the Loop
If you’re spiraling, step away: change location, take a short walk, or switch mediums (talk it out, record a voice note). - Ask the 80/20 Question
What 20% of effort will create 80% of the result? Focus there and let go of the rest. - Remember the Opportunity Cost
Every extra hour spent perfecting one thing is an hour lost to growth, rest, or creativity.
And if you want more science-backed strategies, psychologist Thomas Greenspon has written extensively about the perfectionism trap (APA overview on perfectionism). His takeaway: perfectionism doesn’t improve performance—it stifles it.
Progress Over Perfection
Back to Eli. Eventually, he decided to set a two-hour timer and force himself to send the proposal when it rang. The client loved it—and didn’t notice the small “imperfections” Eli had obsessed over. That experience taught him something many entrepreneurs eventually learn: momentum matters more than microscopic details.
Overthinking feels like working hard, but it’s really just spinning your wheels. The cure isn’t lowering your standards—it’s recognizing that progress, feedback, and iteration will get you further than perfection ever will.
If you see yourself in Eli’s story, ask: Do I need help working through my tendency to overthink and insist on perfection? Consider CoreCoaching. Contact me at Rebecca@MindfulCommunication.com The answer may just be the key to unlocking your next big leap forward.
by rshafir | July 25, 2024 | Blog, Entrepreneurship, Lifestyle
No matter what side of the political aisle you’re on, can you imagine what it must feel like to dodge a bullet? Have you ever narrowly avoided a fatal accident? Perhaps, for no particular reason, you decided not to fly on a certain day or refrained from signing a document that seemed promising but didn’t quite feel right.
Would you wonder if divine providence came to your rescue at the last minute? Or would you chalk it up to dumb luck? Why you and not your neighbor?
Maybe you would probe deeper: Was that near miss a sign to finish that book, spend more time with your kids, or re-examine your priorities?
These are the kinds of thoughts that go through the minds of people who, for whatever reason, escaped death by a hair. It changes you and your outlook. So, what’s your next move?
- Who will you call today?
- What risks would you take that you’ve been putting off?
- What or who would you show gratitude for?
- What fear would you surmount?
- Would you take action—leave that toxic job, start that podcast, propose marriage, etc.?
- Would you discard a bad habit or start a new one?
We live in precarious times. No one is fully protected from misfortune. Do you have to wait for such an event to wake up and move forward in your life?
If you’re a founder who’s ready to leave behind old habits and inefficiencies and finally achieve the success you deserve, now is the time to act. Let’s work together to turn your vision into reality. Schedule a free consultation with me today at Rebecca@MindfulCommunication.com, and let’s start building a more productive and successful future for your business.
by rshafir | January 5, 2024 | Entrepreneurship, Uncategorized
As business owners, it’s a good idea to remember what it’s like to be a customer. As customers we’ve all known the frustration waiting days and weeks for a return call. Our trust in the company or the person we were dealing with dips. Their delay makes us question their competency. We feel less important to them and let down when promises aren’t kept. The longer we wait for a response, the more these feelings fester. Frustration turns into disgust, and we tell others all about it.
Why would you let your customers have that kind of experience?
A 2021 study cited in the book “Be a Unicorn” looked at a survey of >5.7 million leads to determine which ones were most likely to convert into a sale: The ones in which the rep responded to in <5 minutes! Otherwise, the chances of converting them dipped by a factor of 8!
Here are some of the most common reasons founders do not follow up with customers:
- Forgetfulness or disorganization (misplaced the documentation)
- Conflict Avoidance
- Rejection Sensitivity
- Having to say “No”
- Having to apologize
- Admitting that you lack the resources to solve their problem
All of these are solvable reasons for not following up. Most are based on fear. If you take no action to manage these fears, then you have good reason to fear your bottom line.
Check out this article: (16) Facing the Fear of Follow-Up | LinkedIn
CoreCoaching can help. Visit www.MindfulCommunication.com
by rshafir | December 16, 2023 | Entrepreneurship
At the close of 2023, you may be elated, neutral or downright discouraged with your venture’s progress. This post is for those who find themselves more often in the last 2 buckets of “blah.” The more we stay in “blah” the more we strengthen that brain circuit of negativity.
What can you do to weaken that circuit of negativity and, instead, strengthen the circuit of doing and possibility?
Create your personal manifesto. It is a statement of commitment. Complete these sentences and post them in a place to reinforce your “WHY.” Visit your manifesto every morning to reinforce your intention to take action. Read it aloud or silently. You may record it and play it as you prepare for your day. Speak it aloud to others as a way of holding you accountable to your commitment.
My purpose in doing the work, including the boring, tedious stuff is to___________.
My mission is to___________.
I have taken on this challenge because____________.
I have to give myself credit for____________.
My response to the inner critic is to ____________.
I’ll be kind to myself by _________________.
I’ll reward myself for meeting today’s challenges by____________.
Before I go to bed tonight, I will assess my progress and how I can improve tomorrow. I will visualize my best self, working through tomorrow’s challenges with vigor.
Some people rely on external reinforcers to make big things happen. Others look internally ─ they pray, journal, or talk to themselves. Your personal manifesto is a powerful combination of all three. Give it a try.
Share your entrepreneurial conundrums with The COREageous Entrepreneur family of subscribers. Email me at Rebecca@MindfulCommunication.com. I will post my solutions.
Visit www.MindfulCommunication.com
by rshafir | December 4, 2023 | Entrepreneurship
New founders often find themselves awash in a sea of concerns: revenue growth, hiring, firing, funding, family responsibilities, and lots more all at once. It feels like a murky mess. During the course of a day these concerns swirl around in your head while new tasks get added to the mix. Overwhelmed and at a standstill, you’re exhausted, and the clock keeps ticking.
Here’s a solution:
I’m a big fan of time blocking/boxing as a visual way to plan your week. “Compartmentalizing” takes time blocking one step further. It is a process of separating conflicting concerns into different mental “compartments” to manage them separately. This is a helpful coping strategy for getting concerns out of your head and on paper. Compartmentalizing concerns is helpful to your mental well-being, particularly in situations where emotions or worry take hold.
Each area of concern can be a compartment. For example, let’s take “funding your enterprise” as a compartment. Compartmentalizing involves breaking down the larger issue of securing funding into smaller, more manageable components. Carve out a block of time in your calendar for each component:
- Clearly defining the amount of funding required and the specific purposes for which the funds will be used.
Example: Break down the funding needs into categories such as product development, marketing, and operational costs. This will provide a clearer picture of where the funds will be allocated.
- Research different funding sources and methods available to startups.
Example: Divide this task into exploring traditional funding options (e.g., venture capital, loans) and alternative methods (crowdfunding, accelerators). This helps in understanding the pros and cons of each option.
- Build a Pitch Deck:
Example: Break down the pitch deck creation into sections such as problem statement, solution, market opportunity, financial projections, and team introduction. This makes the process more manageable and ensures each aspect is well thought out.
- Focus on building relationships with potential investors.
Example: Divide this task into smaller activities like attending networking events, reaching out to mentors, and participating in industry conferences. Each activity contributes to building a network that could eventually lead to funding opportunities.
- Develop a detailed financial plan.
Example: Break down financial planning into creating a budget, forecasting revenue, and outlining key financial metrics. This allows you to focus on one aspect at a time, ensuring a comprehensive and well-thought-out financial strategy.
By breaking down a compartment into smaller, manageable components and assigning specific times to address them you can make progress on multiple compartments in a more organized and efficient way.
Need one-on-one help compartmentalizing? Contact me at Rebecca@MIndfulCommunication.com. Visit www.MindfulCommunication.com.
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