The 5 Saboteurs of an Entrepreneur

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Entrepreneurship, starting anything from nothing, is brutally hard.



“Conscious” entrepreneurship–building a business that doesn’t just serve a consumer need and generate profit, but also makes a bigger difference–is even harder. Because it’s not just about money, it’s about unleashing expression, connection and potential, and making meaning. Helping others rise.

I’ve worked with hundreds of entrepreneurs and companies, across the spectrum from pure profit-driven to pure mission-driven and everything in-between. Over the years, I’ve seen the same company-killing mistakes made over and over. Especially, when it comes to conscious businesses, there are five that really stand out.

I thought I’d share them below, with the hope that bringing them front and center will help you both see and understand them more clearly, and more importantly, avoid making them and/or fix the ones already “in play.”

Here are 5 things conscious entrepreneurs do that destroy what they’re here to build:

overgiving-11. Overgiving.

As conscious business founders or those who aspire to start conscious ventures, we are driven not just by the desire to build a sustainable company, but by the desire to serve, to help and to make meaning. That is amazing. It is a defining trait and the world needs more of this ethos.

But, this same lens on what we’re building can also create a fierce urge to “give away” as much as possible in the name of service. This seems like the conscious and service-driven thing to do on the surface, but underneath, you end up gutting the resources and financial viability of the business and making it brutally hard to sustain. You also rapidly suck your and your team’s emotional and energetic reserves dry. Until, eventually, you’ve given so much away, there’s nothing left to give, no business left to run.

It’s a bit like the parable of The Giving Tree, except our goal is not to give ourselves away until we’re gone, but rather to build a renewing source of generosity and service that sustains itself, supports us and never runs out.

When we over-give as a conscious business, we end up “serving it away.” And, instead of building a viable enterprise, we end up out of business.

Solution: Finding the balance between being of service and taking care of business is not easy.  But, it is critically important if you want to build a sustainable engine of expression and impact that makes a real difference for a long time. So, create mechanisms to serve as “giving reality checks.” Use a blend of hard metrics—revenue, expenses, resources, inventory, cash-on-hand and cash-flow. Then, add in soft-metric—personal energy, cognitive and emotional bandwidth, social currency and more. Note when either is trending low and take decisive action to adjust course.

presuming-pain-22. Presuming Pain.

Whether we’ve already started a conscious business, or we’re in the planning stages, we’ve got to have a customer and a clearly-defined problem that is causing a specific pain that your business or product or service solves.

Problem is, all too often, we think we know the problem, we believe we are crystal clear about the pain it is causing and know that our solution will get rid of both. And, because it’s not unusual for us to launch a conscious business in response to either us or someone close to us having suffered this same problem and pain, we rely on personal experience to validate the problem and pain.

Thing is, we are sometimes right about the problem and pain in our lives (yet often ignore the deeper “real” problem and pain), and often wrong about the problem and pain in other people’s lives. Even if “we were them,” not too long ago. Because problems and pain manifest uniquely in each person. So, we need to go beyond our own personal experience and find those like us, or those we feel are currently experiencing the problem and pain, and…wait for it…actually talk to them. We need to validate our assumptions about the problem and pain, how it manifests in other people’s lives and also uncover the conversation they’re having in their heads about it.

For conscious business founders, we’re often so driven to help, and so often see ourselves and our struggles in others, we want to move inhumanly fast, to rush past or entirely bypass the validation phase. But, failing to test and validate our core assumptions about problems and pain, before building around them because we think we know what people need and want, that is a massive mistake.

Solution: Get out of your head and into the world. Your personal experience may well inform your understanding of the problem and pain in a very substantial way. But you may also have big blind spots. Better to become aware of them early on, and adjust course, than find out after you’ve already invested huge amounts of time and money.

Find where the people you seek to serve gather, then reach out and conduct a series of well-structured interviews. If you already have customers, interview a sample of them AND then go and interview those you’ve spoken with who have NOT purchased your solution as well. Note where your assumptions have been validated, refuted and everything in-between. Then adjust how you move forward based on this new data.

story-blind3. Story Blindness.

We know in our souls what we’re here to do. We know our mission. We know our “backstory,” the thing that fuels us to do something that matters. We know the people we want to serve, their pain, their needs, hopes and desires. And we know we’ve figured out a way to help. Or, at least, we’re on a path to figuring it out.

It resonates so deeply with us, we just assume “it’s so obvious, everyone will get what we’re doing and why, rush to support us and buy what we’re selling.” Conscious business founders often assume this even more than traditional founders. Because the story is so visceral, personal and the cause so deep, we think “how could anyone not automatically see it, get it and want to participate in it?!”

Except, they don’t. And, they won’t. Because we’ve discounted the critical importance of knowing how to tell our story in a way that leads to clarity, demand and support. I’ve seen this in entrepreneurs across all spectrums, they massively underestimate the importance of messaging and storytelling. They’ll often just “wing it,” creating terrible copy for websites, emails, catalogs, social channels, brochures, decks, pitch-letters and more. Then, they’ll be left wondering why nobody cares and they’re failing mightily.

Effective storytelling and copywriting are mission-critical growth levers, yet they are also simultaneously the most undervalued, underinvested skills in the world of entrepreneurship. They are far more often slapped together at the last minute, then experienced as points of failure instead of the engines of growth they could and should be.

This is an even bigger miss for conscious entrepreneurs, because our stories and message, properly crafted and shared, are often so much deeper and more compelling than more traditional “consumer goods” businesses. We have that rare opportunity to rally people to get behind something bigger.

It doesn’t matter how well we know our customers, how pure our intentions are and how good our solution are if we don’t know how to tell the story of all three, along with why we care, in a way that cultivates understanding without effort, urgency, desire and action.

Solution: First, own the critical importance of storytelling, influence levers and copywriting in your path to success. Then, do a quick, intuitive story-audit. Look at the language, in whatever your primary medium is, that you’ve been using to tell that story, to move people to action, and ask if it’s doing justice to you, your mission and your desire to make meaning. If it is, that’s fantastic, it is also a rarity. For many conscious business founders, it is not only ineffective, it is doing real harm by confusing and even pushing away the very people you seek to both serve and rally to help you.

Be honest. If your story/copy isn’t working, time to make a decision. Either invest in cultivating skills in this area yourself OR set aside the resources needed to bring in the best professional possible to help you. I’ve spent more than 15 years developing my storytelling, influence and copywriting skills and the impact on both my business and life has been immeasurable (I’ve also discovered that I love teaching these topics, which has become an extra bonus for me, as well).

mission-creep4. Mission Creep.

We want to build a business that helps people, that lets us feel fully expressed and connected AND also flourishes financially. To do that, we also need to do something challenging. We need to say no to a whole lot of people we can help. We’ve got to narrow our focus as much as possible, at least in the beginning, and serve as specific a need as possible. This is critical, because it lets us not only focus and preserve our resources, it gives us the ability to tell one story to a specific community with a specific need.

For many entrepreneurs, who often have what I call “entrepreneurial ADD,” this narrowing can be a huge challenge. They all want to serve the biggest market possible. For conscious entrepreneurs, it’s often an even bigger challenge, we are so service and mission-driven that we see need, pain and possibility everywhere we look and we have ideas we believe can help. We want to do them all, at the same time, under the same umbrella.

So often, this leads to what I call “mission creep.” A well-defined starting mission starts getting more piled onto it until, over time, it ends up a jumbled calamity of ideas, agendas, initiatives, values, beliefs, products, services and campaigns that become massively overwhelming and spread resources so thin that everything suffers and nothing ever gets “done enough” to matter. Eventually, it all just collapses.

Mission creep dilutes resources, destroys focus and kills growth. It’s the old parable about the wells. We end up drilling a hundred wells that remain shallow for life, never a one yields water, instead of drilling one that hits paydirt, then leveraging that success to fuel the next and the next.

Solution: Do a quick mission-creep audit. Ask yourself what is the most fundamental expression of your mission. What is the narrowest expression of a community or individual you seek to serve? What is the most focused way to help them? Then, ask how that compares to the full-breadth of what you are doing now.

The gap is your mission creep. It is the space where you need to then look at each piled-on item and make a more deliberate decision. To decide what to say yes to, and “not now” to. It’s not that you’re giving up on all the other potential pathways and people, it’s just that you’re saying, “now is not the time.” Because “yes to many,” means an inevitable “no to all,” when the pursuit of all leaves you out of money, time, resources and business. 

Stay focused, until you have built the structure and resources to begin to add in a more deliberate, conscious and considered way over time. Think serial, not parallel. It’ll help you succeed and also eliminate a lot of stress along the way.

lone-wolfing5. Lone Wolfing.

There’s this mythology in the world of entrepreneurship. The lone visionary. The radiant, driven savant capable of making astonishing things happen. We idolize them, write about them, make movies in devotion to them. Except, with rare exception, it’s a complete illusion.

Truth is, in business, just as in life, nobody does it alone. Nobody succeeds in a vacuum. Peel back the illusion just the slightest bit and you realize, all those legendary lone geniuses were only able to do what they did because they were surrounded by visionary people on multiple levels.

If they need people, guess what, so do we. Not just because entrepreneurship can be brutally isolating and lonely, but because the right people make us not only better humans, but more successful founders, builders and meaning-makers. So, who are those people?

We need teachers and mentors to show the way, help correct course, avoid missteps and shorten the distance from idea to impact.

We need champions to hold us up when we stumble (and we will, more than we’d like) and reconnect us with our vision and deeper drivers when we get lost in the smaller picture.

We need crusaders to hold us accountable when we most want to bail (which inevitably is a heartbeat from our next big move), and continue to act when things get hard (and they always will).

We need parallel-playmates, building their own ventures alongside us, sharing in the emotions, questions, struggles and triumphs that bond us for life and let us know that we are truly felt, seen and understood. Because we are them, and they are us.

And, we need a safe container to gather, drop the facade, get real, do the work and know we’ll be seen, heard and supported.

Solution: #FINDYOURPEOPLE!!! Haha, I know. Not so simple. It’s taken me many, many years to find mine. A big part of that was that I didn’t understand the various people and roles that needed to be present. Start by looking within your community, online and local. Make a list of who you know, or would like to know. You may find some hiding in plain view. Then again, you may not.

The challenge for conscious entrepreneurs is that we tend to be a bit of an outlier, even within the entrepreneurial community. Because it’s not just about money for us, it’s about meaning, purpose, expression and potential. It’s about building not just a business, but a life.

The wrap-up.

There we have it. Five major potential stumbling points along the path to conscious business growth, along with five big solutions.

Whether you’re in the very early stages, or years-in looking to correct course or jumpstart growth, each of the five can either be a major point of failure OR a powerful growth lever. This is a great time of year to reflect on where you’ve been and where you want to go in 2017. It’s a window to get real, own your past and envision and plan your future.

So, spend some time with each of the five. Look at them as invitations to be honest, own your stumbles and your wins. Then commit to doing what’s needed to transform struggle and stuck-ness into momentum and success in the year to come.

With a full heart and much gratitude,


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27 responses

27 responses to “The 5 Saboteurs of an Entrepreneur”

  1. Pearl Paul says:

    Thank you Jonathan, I was thrilled when I came across you and the Good Life Project about 1& 1/2 to 2 years ago – I am just finishing a thesis, waiting on a diploma and have not yet started my business. I have engaged in two other business/coaching/mentorship programs both of whom offer membership to their small niched inner circles – and yours is the only one that I feel an alignment and connection – but until I have an income I am not able to pay for the membership to your 108 group. Once I get my business up and running and start earning – 108 is a place I will invest some of my earnings. My only hope is that you will continue to offer 108 groups over the next two years. 2017 is setting up and launching and testing and re-crafting… I am hopeful to join in 2018. Pearl – Loved your books – How to Live a Good Life and Uncertaintyl

  2. Joseph says:

    Thanks Jonathan! This is a great reminder. I know I’ve done a little bit of all of this as I’ve started my business. The good ole’ journey of entrepreneurship. 😉

  3. Great article! Focus is so important… I’m sure many of us have so many ideas and big visions. There has to be a day one, year one, etc., that might seem really small… this is where I’m at… I have to keep reminding myself that focus, intention, connection, communication, etc., right now are so important to making the big vision reality.

  4. Laura Neff says:

    I *just* got off a call with my teammates at our small consulting firm, and I had a huge ah-ha that aligns w/ #2 (Presuming Pain) above. There’s a paradox about this…we need to be seen as some kind of expert for people to trust us enough to invest in our services (whatever they are!), AND we shoot ourselves in the foot if we go in assuming we know what’s going on with them. More importantly, the latter can both rob them from discovering what they don’t know about where they are, what they truly need, etc. and can also rob us of coming up with solutions that are targeted in the most powerful ways. SO, I just came up with a new mantra…”Be the expert in not knowing!” 🙂 At the very least, this is my new “come from” way to be at the beginning of a prospective client conversation. Can’t wait to see what it opens up!

    • Laura Neff says:

      (The biggest thing this turns on its head for me is sourcing my personal sense of worth/value from “knowing” to the idea that my highest worth/value could actually come from “actively not knowing.” <- Whaaaat?!?!)

      • Jonathan Fields says:

        Yeah, totally get this. We have that drilled into us from the earliest time. Our value lies in our answers. What I’ve seen is that greatest value that the greatest consultants, founders, makers and leaders all provide is in the way they observe and question differently. Ray and Charles Eames are great examples. They were renowned as designers and makers, but really what they were stunningly good at was seeing differently and having a unique process of inquiry.

        • Laura Neff says:

          That’s it. And at this point for me it’s really a process of unlearning…unlearning beliefs about value/worth, unlearning patterns of listening and seeing, unlearning what the world, culture, and even competitors have taught/shown us about “what’s so” and “the right way.” And then adding in a big dose of presence, curiosity, willingness to not know…ah…sounds pretty damn lovely, actually…! 😉

  5. Ben says:

    All 5 points here I find myself struggling with as I start to lift my first conscious business off the ground. Before, in my first venture, it was much easier to just follow the hard metrics and satisfy a customer need better and more efficiently than the competition. But now, being struck with the fierce desire to build a “conscious business.” I am in new waters. Territory unknown to me. I am so grateful for being in this community who are on the same path. It is a light at the end of the tunnel.

    Any suggestions on great resources for developing storytelling/copywriting skills that speak to the more purpose driven crowd?

    • Jonathan Fields says:

      Hey Ben – Yeah, it’s interesting how traditional entrepreneurial culture often “writes off” conscious business as “for those who can’t hack the hard stuff,” instead of for those who actually want meaning and live, bundled with profit and prosperity.

      Sadly, I don’t have many resources for copywriting. I’ve learned over the years by studying directly with certain people, reading massive amounts (including books that date back to the 1940s) and doing and analyzing what I write as well as deconstructing the work of many of the greats (some who’ve become friends). I teach a solid amount of this in the business-oriented programs we facilitate (and will again in The 108), but you can also learn a ton from massive self-study.

      Be sure to also read Eugene Schwartz’ Breakthrough Advertising for copywriting genius (it out of print and can be pricey, though), and familiarize yourself with Joseph Campbell’s work on the monomyth or hero’s journey as starters. Hope that helps!

      • Ben says:

        Thanks, Jonathan. I will check out all of these resources and look hard at the 108. I am in the very early stages of building a tribe, but maybe that is where this would be the MOST beneficial…

        With Gratitude,


  6. Lisa Milich says:

    Thanks Jonathan! So wish I knew more about this before I started. So many things resonated. It’s been painful, but so relieved now to restart in a way that really works. Blessed to be part of your tribe!

  7. Thank you Jonathan,
    A friend sent me this and I can honestly say that I am guilty of all 5. 🙂 Awareness is key, so now I’m off to work on a few of these today!
    Thanks again,

  8. Jonathan…..nice!!!!!

    For me…
    with Number #2…….
    “Understand the problem/pain”

    ….is half of the SUCCESS fo my company!!!!

    1. First understand the problem….
    2. Fall in love with the PROBLEM …not the SOLUTION
    3. EVERYBODY in the company has to understand the PROBLEM first….and I mean everybody!!!

    The SOLUTION…usually is easy!

    saludos Jonathan…..miss u

  9. therese says:

    Hi Joanathan
    I bought your new book. When will the rest of the book be coming out?’


  10. Dion McInnis says:

    One of the best, most cogent views of that which both empowers and debilitates conscious entrepreneurs. Excellent!

  11. Yvonne W says:

    Holy Moly!! *sheepishly raises hand for each description…

    This is so good on so many levels (Love the graphics btw!) I think for mission-driven idealists like me – overgiving is so easy to do! It reminds me of what you said in your book “How to live a good life…” you said “before you can choose joy, you have to choose you.”
    Yes, presuming pain has been a surprising mistake for me. And your riff on getting in the room (last year?) really gave me the courage to get into the field and boy, things are really different on the ground. I think this is especially important in this era of online biz and lifestyle design.
    And, Don’t get me started about lone wolfing. This has been the hardest to shake – it is so easy to lose track of time while creating in solitude or thrashing in overwhelm and how that time suddenly creeps into isolation. Thanks to being surrounded by the GLP tribe and regular self-reminders to reach out and connect, it is getting easier and easier.
    Mission creep – sigh… Slowly but surely, the will to stay focused on a narrow niche is stronger after some hard times cultivating Discipline but oh, the temptation is sooooooo strong – I mean so many problems in the world, so tempting to expand the niche just a tinier bit! lol
    I am curious, Jonathan, which one has been hardest for you to learn and how did you overcome it?

  12. Yvonne W says:

    P.S: I just realized that the topic of the TED radio hour I am listening to this very moment is “Giving it away” – lol Did I say overgiving was a past struggle? lol

  13. Tracy says:

    Thank you for these unexpected 5 things! I’ve been reading up on entrepreneurship, and this list is unique — perhaps because it’s tailored to conscious businesses. It’s true we need to find a balance within what we do and keep honing how we’re approaching our people. Awareness is key!

  14. Carla Cupido says:

    Awesome article Jonathan. Thank you! Great reminders for me.

  15. Cassia says:

    So timely. I’m a saboteur for certain and am taking this month to really dial in on what I want 2017 and beyond to bring for me and more importantly what I want to offer it. Having this little list to refer to periodically will help me to identify when self sabotage is taking over.

  16. Hi Jonathan – all five of these are so valuable and I’m sure resonate with almost every CEO/COO out there! I would add that in addition to working to not “Presume pain,” I find that I also need to be reminded not to “presume willingness to pay for pain relief!” The lessons learned on this are steep, as sometimes we develop effective and helpful solutions that offer pain relief but the customer’s pain is not deep enough to motivate them to pay for a solution. This is often an interesting conundrum that then drives many of us right back into Problem #1 “Giving it away.”

    Love the 5 points… and realizing how much they all overlap and bolster one another! Appreciate the post.

    • Jonathan Fields says:

      Definitely a strong follow-on. Pain must not only be validated, relief must also be valued. 🙂

  17. Jody says:

    Ah yes! So true. I can truly relate to points 1,4, and 5. Over-giving is so hard when you first start out, because you want to differentiate yourself, and provide ‘value-add’. The problem is that you have to have the base before you can do the value-add, else you have to go home. Very insightful, and accurate. Thank you.

  18. Rick says:

    Wow. This was so good, so on point. And, after listening to some Tom Waits, your prose takes on a certain ring and cadence that’s almost beat poetry. Glad I showed up here. Looking forward to more. Thanks for the lessons.

  19. […] The 5 Saboteurs of an Entrepreneur […]

  20. Ashley says:

    wow, I feel like this was written just for me! what perfect timing as I am still in the beginning stages of fine-tuning my vision & crafting a business plan. thank you!

    – Ashley

  21. Joel says:


    It took years to overcome point number 3 and even as I say that, I don’t believe that I have truly overcome it. In fact, I don’t believe any one person ever does.

    As human beings, we are “programmed” to believe that every idea, thought, and notion that we come up with will benefit society. As true as this might be, without practice most aren’t good at parlaying that into a relatable story. Even with practice, no one ever becomes perfect at it.

    I know I haven’t and probably never will.

    The most that we can do is to aim to become the best that we can at storytelling and use that to its best ability.