Created with Sketch.

Escaping the Lonely Entrepreneur’s Club

All across the world, lights burn bright into the night illuminating solitary windows. Office block, apartment building or suburban sprawl – it doesn’t matter. Every night, where ever people live and work, entrepreneurs burn the midnight oil.


While the civilians rest their weary heads, business owners pour coffee and sigh over piles of post-its, stuffed inboxes and more. Even as the tangible to-dos stack up, the intangible to-thinks tower ever higher. The entrepreneur’s mind keeps racing.

Is it perfect? Will next month’s revenue be on target? Will that key account close? Will people buy your stuff?

If you’ve experienced nights like these, you know it’s lonely being an entrepreneur.

Loneliness is the entrepreneur’s curse. Your role as the decision maker, bread winner and overall renegade definitely makes you a winner, but you have to pay the price. Making those decisions, winning that bread and living that outlaw lifestyle is mainly going to happen in a party of one.

When you’re alone on the entrepreneurial road there is one problem that stubbornly resurfaces, again and again.

Lack of perspective

Being a lonely entrepreneur is uncomfortably similar to being a fish in a bowl. No matter how many times you swim the circumference, it’s still really really hard to see anything outside.

You’re trying to solve big problems and, scarily, life and business all start to feel a bit repetitive. You know you’ve fallen prey to some kind of mental script or psychological pattern but there isn’t any mirror in the fishbowl to examine yourself in!

That’s the big advantage of a companion – perspective from outside the fishbowl. The point of view that looks in from the outside.

As an entrepreneur, you’re probably headstrong and independent – to an extent. When things are going well, it feels good to be in that “you vs the world” position… because you’re winning!

Entrepreneurs don’t notice the absence of support and perspective until the dark moments. It’s when things appear to be falling apart that the confusion, spinning wheels and fear kick in. Sometimes, these demons strike so hard and fast you end up so completely lost that you don’t realize you’ve simply lost perspective.

Perspective is the solution. So how do we get it?

My call to action today might actually surprise you. I want us (you and I, dear reader) to tackle this problem the other way around. Here’s what I mean…

Entrepreneurs need the perspective of other entrepreneurs. They need friends, mentors and coaches who get it. Specifically, they need people who hold space for them – creating the environment where vulnerability and uncertainty is welcome.

We need to have meltdowns. They’re natural and cyclical in nature – losing the plot completely is part of being human and definitely part of being in business.

When someone “holds space” for us, they’re given us a venue to go on that emotional journey. It might be a physical environment (a safe space) or it could just be an ear over the phone, or an open inbox.

Who is holding space for you?

You need someone to turn to in those dark moments. You need someone who can instantly offer a perspective from outside the fish bowl.

Overall, most entrepreneurs I meet don’t have nearly enough of this form of support.

Who are you holding space for?

Let’s tackle this problem counter-intuitively.

I’d like for you to make an effort to hold space for someone else. Do you know other entrepreneurs? If not, just introduce yourself to one in the comment section of this site – there’s thousands of people reading this, so none of you have an excuse!

If you’d value having a friend, mentor or colleague who’s there to give you a fresh perspective when you need it most… then be that person for someone else.

Call it karma. Call it problem solving. Call it whatever you want. By becoming a master at “holding space” you become a little bit of a mentor, coach and entrepreneurial shrink. You’ll be doing meaningful work and if the entrepreneur you’re helping is on a mission to change the world… then, in a small way, you’re contributing too!

No business owner who’s ever had a taste of effective coaching or mentoring will ever go back to a life without it. This is because they get it. They have a very real experience of the value of space held and perspective given.

Personally, I count five people in my list of unofficial coaches – the ultra close support people whom I have permission to be totally vulnerable in front of. My network includes some remarkable people, which is why I count a doctor of clinical psychology as one. However, not a day goes by that I’m not grateful for the perspectives given by my old high school buddy… who is more or less a starving artist. Perspective is fresh – regardless of who is giving it.

Not one of those people include my “significant other” and this is (more or less) why. Don’t get me wrong – spousal support is crucial, but I’m talking about something else entirely here.

I know too many entrepreneurs who don’t have anyone or worse, think they have someone holding space for them who isn’t.

Perspective Karma

I can guarantee that if you make the effort to be this kind of friend to another entrepreneur in your life, you won’t have to look far when you need a perspective. This is a no brainer, isn’t it?

So, if this concept sits well with you, go out and hold space for someone else… starting today. Here’s a quick fire guide on how to do it:

  1. Create an environment where the other person is totally safe.
  2. Actively listen. Holding Space is about giving someone room to express themselves and their emotions entirely – so quit thinking of what to say next and hear them.
  3. Don’t offer solutions – allow your friend to arrive at their own conclusions.
  4. Ask questions, but never questions that lead.

Great questions for holding space

  • “What do you need?”
  • “Where are you now?”
  • “Where do you want to be?”
  • “What has to happen for you to get there?”
  • “What can you take responsibility for?”
  • “What have you learned?”

I hold space for a job. My whole business is built around creating the best space and perspectives – the kind that support and nourish entrepreneurs to do extraordinary work. The world needs more successful entrepreneurs, which means that entrepreneurs need more support.

I wrote this post hoping you’ll join me in some way. My consulting isn’t scalable – it’s boutique and premium (although you can get a free test-drive) and there’s still a big need for entrepreneurial perspective out there. That’s a perspective you’ve already got and I know it’s worth sharing, with one other person minimum.

If you’ve got questions or want to know more about Holding Space, let’s chat it out in the comment section under this post. I’d also love to hear from you about your experiences holding space for others and/or being the beneficiary of valuable perspective.


+ Add Comment
  1. Holding Space – that is the most beautiful phrase. Not only does it describe the role but create a visual of what is needed.

    Your posts are fascinating to me. I find myself often writing and rewriting comments as I am worried my first reaction is too personal for me to share in such a public forum.

    So I will start with a question. How do we protect our friends, the entrepreneurs who are being misled by people who want to steal their space, and not hold space?


    1. Great post, Peter! Terrific question you are posing, Ainslie. And I can tell I have been hanging around Peter too long. My first reaction to your question was “And how is that working for you?” That response is not TO you (unless that helps somehow) but as a question added to the wonderful list of “space holders” above.

      However, the instant it entered my mind, I realized it is sort of a higher level ninja, don’t-try-this-at-home kinda question. If I am able to say this to someone without emotional attachment to their answer, I might be saying something useful, and giving them breathing room. But if I am saying it from an “I’ve already decided what you need to hear/do and I’m just waiting for you to realize it” sort of place, it will not come off as helpful, no matter what words you use.

      I find the very act of “holding space” requires a loving detachment from our own judgements about THEIR outcomes. However…if I need to shove someone out of the way of an oncoming train, screw my emotional detachment. Tough choices! Some days, our friends need us to hold up the truth for them, as well…precisely BECAUSE we are emotionally attached and anyone who cared less about them wouldn’t even try. But when I whip out the radical honesty…I better be ready to take an emotional bullet for the friendship!

      For me, holding the peaceful, open space is the right answer more often than not. But it is surprising how difficult peace can be.

      1. Hey Cory,

        Awesome, insightful and super valuable comment. THANK you.

        You’re right about the question too – I didn’t include “How’s that working out for you?” in my list of suggestions because that’s definitely one that you should only be asking if you’re confident you’ve achieved “Level 6 Laser Lotus” in the hierarchy of …. being a switched on human who gets people.

        Asking folks “how’s that working out for you?” after they present a description of a behavior they ASSUME is the *only* choice they’ve got…. is guaranteed to shake up that assumption powerfully.

        So powerfully that it’s a “don’t try this at home” one … although I know you’ve got the chops to add that one to your quiver of penetrating questions. 🙂

    2. Hey Ainslie!

      I’m glad to hear this post hit the spot for you!

      If I understand your question correctly, you’re asking how to shelter your entrepreneurial friends from folks who are USING them for support… in a non healthy way?

      The answer, I think, is education. Send those people here, to read this post – or just talk to them about what YOU value in terms of “holding space”. By exposing them to the true value of this concept, they’ll learn to spot the difference between the good and the bad. 🙂

  2. Peter, “holding space” – beautiful words. I loved this post. I just came back from Blogworld and I talked about the importance of community – not as specific and articulate as you are doing now but my point was to be there for your community and to build relationships so that you can turn to them when your motivation ebbs and you need to rely on support and by the same token, you can be there for your peers when things go awry in their life! It is imperative that we have support. My support is my husband, my brother who is my business partner, and my blogging community (especially a precious few within it)…. thanks for a great thought-provoking post.

    1. Hey Farnoosh! How was blogworld?

      That was my real point here… that paying it forward is really the only way to make this work on a grand scale. Hold Space for others first… before you need it yourself.

      Awesome to be part of the same community Farnoosh 🙂

  3. Great post – this is hitting the nail tight between the eyes!
    It is funny a thought came to me while reading this post and I realise I feel most alive and of purpose when I am helping or just being there for some of my friends when they are going through their “melt-downs”. We all need someone the we can be there for and someone to be there for us.

  4. The questions are most helpful! I have other self-employed friends, and we act as each others’ support, but these questions will really ratchet up our problem solving, thank you!

    And while I loved your “why spouses destroy business” post (and learned from it), I won’t nix my spouse out of my problem solving. He and I are in totally different industries (and totally different creative pursuits), and we offer each other perspective on problems — so valuable, because we get an outside, completely removed, “consider this” perspective — which gets tricky when you’re already wrapped up in something. We never coddle each other.

    If any other commenter/reader wants to swap ideas with me, please connect w/ me via my website. Thanks, Peter, and cheers!

  5. “Entrepreneurs don’t notice the absence of support and perspective until the dark moments” how true this is….and when the meltdowns come, as they invariably do, they happen with force, in solitude, and without support.

    I love your idea of “holding space” and while I find myself frequently doing this for others (and feel privileged to do so), somewhere along the journey I seem to have become seen as this dependable rock, this that has her shit together, who doesn’t need support.

    Obviously I’ve contributed to this impression, there are barriers that I’ve constructed that have served my needs at some point. The difficulty lies in how to restructure or demolish those boundaries to be privileged enough for someone to “hold space” for me.

    Thanks for prodding at the soft spots!

    1. Hey Jackie!

      I’ve come across that “phenomenon” many times – the whole forgotten, dependable rock thing. Thing is, the solution is actually simple: just ask.

      If you’ve really been giving that space to a bunch of people for years, I can GUARANTEE that the only reason they’re not giving it back is they just don’t realize you need it. So just ask. They’ll be tripping over themselves to help out.

      And if that doesn’t work, email them a link to this article 😛 <-- that's the passive aggressive option haha

  6. Important post Peter,

    Very early in my graphic design business I found a design buddy. Seven years later we still maintain our buddyness. It made both of us kickass designers and kept us sane when dealing with insane situations. In addition to my buddy, I belonged to two design groups. Now I just belong to one, but we can ask each other for technical, printing, design info. We also get together socially.

    Great group! I highly recommend finding a buddy. I find being my own boss, working in a home office LESS LONELY than when I toiled in a sea of cubicles filled with people I had no underlying connection to.

    Go figure.

    Thx, Giulietta

  7. Fascinating post. It really is a “You are not alone” cry. Often we feel alone as others don’t quite understand our relentless persistance or question our actions.

    I have 2 local business mentors and I couldn’t keep sane without them. As for holding space for others, well … working on that!

    Warmest regards.

  8. Like your reader Greg, I am at my best when I’m supporting or helping someone when they are in the thick of it.

    That feeling, we’ve made it, when you are part of the ‘we’ is second to none.

    Such an interesting site.


  9. Great timing on this! I’m just in the midst of writing a post about the lessons I’ve learned in my first year of entrepreneurship, and one of them is “you are not alone”.

    My partner and I are both small business owners and it’s just so amazing to have someone so close as a sounding board, cheerleader and shoulder to cry on. My friends and family are wonderful, but if you’re not an entrepreneur, you don’t really get it.

    I am also fortunate that my business revolves around me working with small business owners and entrepreneurs. Supporting them and being there is not only super rewarding, but it helps me as well as I can learn from their struggles and keep them in mind when I’m having some troubles myself.

    Thanks for the post Peter:)

    1. Hi Martina, thanks for joining the discussion. You’re in a cool position – the whole entrepreneurial power-couple dynamic is a great one, because the other person just *gets* it.

  10. This is what helped me through the rollercoaster ride of my entrepreneurial (and social, relationship, etc) life of the last 4 years. I am a member of Entrepreneurs’ Organisation and one of the 3 pillars of that organisation is a monthly meeting that we call forum – in my case with 8 peers who are each entrepreneurs. 3 rules: proactive (seek to share), confidential (what is said here stays here) and gestalt (only speak in first person, share experience, never advice). It only became clear how important this was to my life after the crash… Thanks Peter – love the words “hold space”.

    1. Hi Conor! 🙂

      The EO is definitely doing it right – those three rules are ones I would recommend all entrepreneurs borrow for their “holding space” sessions with colleagues/peers.

  11. Holding space is one of the reasons why I blog about business and entrepreneurship as it creates an avenue for me to support others out there who may be going through this unusual journey all by themselves.

    Ironically, I am also in the business of holding space and creating that needed outsider’s perspective to entrepreneurs. But that doesn’t in any way negate the fact that I also need the support of these entrepreneurs too. So creating the blog is my clarion call to others that they are not alone any longer and also a means of others reaching out to me too in return.

    I really like the way you put this across and I have hyperlinked this post to one of mine about the dark side of entrepreneurship.

    Thanks for sharing. I wouldn’t mind us holding out spaces for one another?

  12. It is about 6:15 am where I am, awake since yesterday as usual. For some reason I googled “lonely entreprenuer”. I have been finding lately, more than ever, that having a way to “drop the act” of the persona I have come to acknowlege as essential to the survival and evolution of myself and professional life, is both necessary and extremely difficult to obtain. I was fortunate enough to be given an hour of a gentleman’s time a couple months back, where I was able to feel comfortable enough to tell the story of my last few years from stepping into the business scene to present day. I had owned and operated a food establishment for the last four years and was in the process of opening up my first project from the ground up (I had bought the previous place from my old boss). I was 22 at the time, and the next four years would prove to be the most challenging, rewarding, heart-breaking, and overall insane time of my life. I had no partners, so I took an extremely quiet and secretive approach to the whole situation, I also did not have any sort of guidance or mentoring (outside of those I was paying for a service… and I am sure most of you know – listen at your own risk). Anyway, all the decisions were my own – all the mistakes, all the blame, all the risks, all the consequences, and all the hours after-the-fact the sit alone and try to analyze it all. Now, it was very easy to dismiss the whole “lonely” factor, as employees and customers would soon be here. I figured making mistakes and screwing things up was all part of the game. This is true, however I think that perhaps a good number of these mistakes were a result of decisions I made with the thought that “Well, I’ll try this – it seems right, but if it ends up failing, well… failing is part of the whole learning process. Without someone to pull me out of my “tunnel vision” with either direct advice or non-objective conversation, I had to double-check, constructively criticize, and disprove and idea I had for the sake of control. This works about as good as it sounds. I am 26 years old now, and I think that the most terrifying thing to me about opening up this establishment is the fear that I will fall into old habits, and shell-up my personal life – reasoning to myself that anywhere and anytime I am in public, that I am representing my business and must conduct myself in a proper manner – you never know who is watching or listening… and business can be a dirty and delicate game. I can’t help but think that my complete absence of personal life (relationships, family, social) is of my own choice. I have never heard otherwise, but then again, who could I ask? There were, and are so many questions I want to ask… but it seems counter-productive and sometimes detrimental to ask these questions, especially if you are asking someone who is clueless to your reality and circumstances. This gentleman I spoke to simply listen, and asked only a few questions during the entire time. Mostly it was me talking, (rambling on and stuttering mostly) extremely un-fluid without grace or confidence. I was actually very very nervous about the whole thing. Many of the things I was telling this guy, I had never said out loud before. Of course these things had all happened to me, but I was able to either quickly dismiss them, or keep them to myself, hidden from absolutely anyone else in the world. I initially wanted to have this meeting-time because I had recently began to lose my focus and fire to keep moving this project ahead… to the point where I knew it was a serious issue and needed to be dealt with. If any of you have opened up a food establishment from the ground up, the process is a very defining experience the first time – at least for me. Being able to physically speak some of the feelings I was having, and stresses and trials I was going through really gave me somewhat of a “ground” or perspective (mentioned above I believe). It didn’t provide me the answer to my problems or give me some spiritual awakening or even a boost of self-esteem. But it gave me a different way of looking at things – just by saying outloud what was in my head. With this, finding the problem was made more clear. I think most of you would agree – “If I know whats wrong, I can fix it”. As for the whole “lonely entreprenuer”, I have found that personally, defining my cause and purpose for doing the things I do and sacrifices I make are noble and pure. But I still get hit hard emotionally sometimes when its 3-4 or something in the morning, and I’m sitting by myself in this big empty space working… even now as I am typing this out on my phone thinking about how I should be doin stuff already. I only read the literature on this page leading down to where I could write a post, and honestly, as of right now I don’t plan on looking much farther. Hell, I don’t even really know what kind of webpage this is, only that the audience is likely to have some way to relate, and in turn my words aren’t perceived as a boastfull or sob-story. I believe the author of the text from this page will help many people out with those few words, regardless of their intentions, simply because of their truth. May we all find a safe outlet to nurture our evolution as entreprenuers and people, and provide others with the same courtesy.

  13. What an interesting website! I actually got here by googling “lonely entrepreneur”. I am just curious, I get the most lonely when I get scared and not have anyone to just spit out what I am scared about. What about you? Do you get the David vs Goliath (your competitors) kind of feeling?

    1. Feng, I can only speak for myself – but I’ve found that the path of an entrepreneur can be absolutely terrifying. It almost seems like the epitome of the “keep it all bottled up inside” saying… because we all know the consequences of showing any kind of weakness to the public world – emotional even more so than physical. I would like to think I know exactly what you are talking about. It really sucks to have no one to talk to about anything. I have found that it is incredibly important to do something (anything) to keep things in perspective for the sake of sanity. After all, if we only are able to talk to ourselves about issues… it is like spitting on a bonfire. There are some out there that speak freely and completely uninhibited with everyone – employees, customers, associates. I envy them. I have no knowledge of the type of business you are in, but I think the “David vs. Goliath” feeling is felt universally throughout all sects.

      I believe that the most valuable and safe-guarded abilities of an entrepreneur are discipline, adaptability, and passion. I also believe that this may be the basis of the “entrepreneurial spirit” or whatever (I never studied business) that I hear about now and then. Also, I am not religious by any means, though I do of course know the story of David and Goliath. Discipline, adaptability, and passion perhaps define David now that I think about it. I have discipline and adaptability represented with tattoos and plan on adding a representation of passion before my new endeavor goes public. Anyway Feng, being lonely has unfortunately been a constant weight that I personally have been fighting for a while now, and more so than ever in the last 6-months. If I could say anything to your question, it would be “yes”. Stressful and trying times are magnified when you have nothing or no one to confide in – and let’s face it, you can’t really confide in yourself… can you really find solace in the bearer of chaos (yourself)?

      Maybe it is because these times can be very humbling. So often we hold or represent positions of power and influence that it is the most unlikely and simple of things that can cripple us… like the downfall of Achilles (an arrow… damn! and getting hit on his foot… what the hell!?). I have not done any studies of this tale, but in some ways Achilles and entrepreneurs share many traits. He was a great man and warrior on his own, but he also lead a group of fiercely loyal and skilled men the Myrmidons. He represented an idea, or cause, that was only alive when he breathed life into it. In the battle of Troy, when he withdrew, the Myrmidons became dormant which spread to crush the morale of the entire Greek army… fine raw material but nothing more (I am referencing the movie…). No artist to shape them into something great. Achilles was that artist, he was able to inspire and lead these men with his passion. Extremely disciplined because of the passion and bond shared between a leader and his followers. Through this, they were able to adapt and overcome opposition in such a way that their story will be told forever.

      I believe most entrepreneurs can relate to Achilles in some way. Almost all of us are leaders and fighters in some way. If you have employees, (or anyone who you pay) you delegate and lead your crew to complete the job or objective. Even if you have no employees and act alone, you are leading. Representing an idea or dream can be more important that direct leadership – while giving specific directions or orders to your crew, they carry out their task according to you. With an idea, it is open to anyone to act upon. Be it next door or half-way around the world, there are no limits to the impact an idea can have on the world… it is after all an idea, and not a specific thing. Employees are limited to their orders and nothing more, whereas an idea has no parameters other than its defining purpose, and can be added to, modified, strengthened, and immortalized as long as the idea lives. Leading is never an easy thing. And true leaders reluctantly take up the position because of their own personal passion for a cause. Those that say that leadership is easy, beneficial, and prestigious have never really led (I think that’s all a quote from somewhere).

      Where am I going with this? I don’t know. Is there a purpose or message some where in all these ramblings? Probably not. About an hour ago I received an email notifying me that my grandmother had passed away last Friday. There’s no way in hell I am going to be telling anyone about this, I don’t trust myself. I actually stumbled upon your response in my spam folder and subconsciously for this reason am taking advantage of this great outlet once again. You did not ask for any advice or counsel in your post, but I will offer it regardless for what it’s worth. We are not all fortunate enough to have friends, family, or anyone to look to for support or refuge. But, we are given the opportunity and power to make change in the world. If you can not find comfort and reassurance in others, find it within your own cause – your purpose for doing what you do. In doing this, you will never be alone. You vent your distraught and vulnerability with your actions. Be relentless and fierce in your pursuit of your cause and you will never be alone, even if you can not see or hear anyone following. And also be willing to accept defeat, loneliness, and chaos, as they will certainly be around to keep you company whoever you are, as sure as fire burns. If anything, these are important tools which constantly test us. To see if we are worthy of holding such a position. No soldiers follow a losing general, and no one bets on a horse that finishes a race 80% of the time. Each and every time we conquer these things, we are proud and also humbled. We need to be reminded we are special, and capable of accomplishing our end-goal. We remember those who have been overcome and fallen to these obstacles and honor them with our drive and passion to endure and claim victory (starting to sound like a movie almost! though life can seem like a damn Hollywood movie sometimes).

      It’s lonely at the top.
      To lead is to be alone.
      Leaders do not inflict pain. They bear it.

      You’ve heard them all before but with new-found respect I would bet. It’s part of the job description and always will be. Whatever you can do to manage loneliness will probably be your most valuable ally – and at times your only friend. Feng, I do not know you or your cause, what you do or where, but I tip my hat to you and everyone else in the world who do not succumb to the title “lonely entrepreneur”.

      If ever the need for solace by an open-ear should arise, it is only a few key-strokes away. For you are not alone. We are many that fight this silent battle – and in silence we will prevail.

  14. Mannnnn! I too Googled lonely entrepreneur. It’s soo damned lonely. I feel the most loneliness during my high times. No one to share the excitement, the joy, the progress with but much worse the fear. I am sometimes so afaird.. And sometimes I feel bipolar – riding high off the numbers today and sinking low with the fear of failure tomorrow. I’m always preparing/expecting the worse. And sometimes when everybody else is celebrating our success. I know I must seem crazy. Nonetheless I wouldn’t give it up for the world. Entrepreneur For Life. I make myself available for holding space and thank-you peter for this post

  15. Today I started a blog sharing my experience as a “lonely entrepreneur”. There are so many of us out there and I want to tell people about the emotional side being a solo-entrepreneur.

    I am so glad to have found this post and this website. I don’t feel so lonely now 🙂

  16. Amazing Article. I’ve been struggling with “being alone” as i start my new business. You’re all welcome to send an email. Ready to hold space for someone. “Where are you now and what do you need?” Let’s make this happen one entrepreneur at a time.

  17. Bingo on-line – Wir haben eine eigene Bingoexpertin, die sich intensiv mit
    dem Thema Online Bingo befasst und eine Vielzahl ausführlicher Informationen bereit gestellt hat.

  18. At Guess Online you’ll find the newest news and for reference test betting articles, we present you tips on how to
    open an account to completely different homes to bet you do not find what you are
    in search of, which covers every side of on-line betting.Featured Recreation –
    Blackjack, including the NFL, comparare Prime-notch bookmaker online, blackjack is a fun sport to play on the web, newest information from
    the world of sports and gambling.M has them all for you right here!You Guess Online is full guide to
    wager on sports activities, at a multi-participant table and even in an online blackjack event.M gives
    a variety of on-line slot opinions where you’ll find related slots
    to Aladdin Slots.

Leave a Comment

Outsource your battle for Focus and Productivity

Commit Action’s Executive Aide service helps business owners become the highest leverage version of themselves possible.

Visit Peter’s other business