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The Truth: Why Solopreneurs are destined to stay that way forever

Most solopreneurs have dreams or vague plans to one day make it to the big time. A proper company and staff to boot. Whether it’s an in-house team or outsourced global workforce, every business owner dreams of growing the family, even if only to a single virtual assistant.

Yet such dreams are almost never realized.

Despite the lower-than-ever cost of bringing outsource talent onboard, entrepreneurs still struggle more than ever to actually getting around to doing it.

I have a nose for self-sabotage and something here reeks of internal conflict! This post explains why you still haven’t hired that person you know you should. Hint: It’s all in your head.

“I just can’t let go”

Famous last words of the archetypal solopreneur who endlessly procrastinates hiring the help they need.

Entrepreneurs are smart cookies and they’ve heard about this psychological stuff. They think they’ve got their reasoning, for not quite yet hiring someone, down pat. They tell their friends and family that it’s all about “control”.

It’s a nice idea. You’ve built a business that is so reliant on your genius that it requires your constant attention. The very idea of finding someone talented enough to take even half of one of the smallest reins… is laughable.

Set back, relax and smile. Your mother in law is convinced you’re indispensable.

I, on the other hand, think that you’re trapped. If you can identify (even slightly) with the description above, then you’re a hamster spinning in a wheel. Sure, it looks good to those in-laws lacking commercial know-how, but the rest of us know you’re stuck.

Your excuses for not hiring help are way off the mark. So what is really going on?


Like all self-sabotage, the true driving force behind what I call “expansion avoidance” is cold, sweaty fear. The kind that keeps you up to three am, twisting your insides.

Entrepreneurs aren’t worried about control… they’re terrified of failure and there is only one thing worse than failure? Failure in front of an audience.

When you transition from solopreneur to fully fledged entrepreneur, you suddenly have a lot more riding on your success. You can’t mess up, because you’ll look like an idiot. Even your outsource drone in South East Asia might laugh at you.

Staff mean that you have to have your stuff so sorted out that they always have something to do. For the solopreneur this is a lot harder than it looks – most don’t even know how to prioritize their own to-do list, let alone a helper’s!

The fear of responsibility

The prospect of working with others brings cold shudders to the spines of solopreneurs simply because of the new responsibilities that come with it. You’ve got to look after your team and lead the way as a shining example!

Scary right?

The fear is good

In my ebook Demystify Your Fear I talk about the two types of fear – appropriate and inappropriate. The later is the kind of BS terror based on past conditioning that needs to be ignored. The former, however, is highly useful. It’s the kind of fear that stops you doing stupid things.

If you’ve procrastinated hiring someone because of deep-seated fear, I’m not going to tell you to get over it. In fact, I’d suggest that you pay careful attention to the emotional signal you are experiencing.

Appropriate fear has just one meaning: That there is an event coming up for which you must prepare.

That’s why fear is so useful. It keeps us safe. It is a message from our unconscious mind, telling us we are not (yet) ready to face the danger.

If you’re fearful of hiring staff, pay attention to the signal. You’ll never get business advice as timely and intelligent as the raw “feedback” from your gut-instincts.

There is only one thing worse than an entrepreneur endlessly procrastinating hiring staff. It’s the entrepreneur who procrastinates then leaps – hiring despite their fears. Sometimes it works out, but in my experience it’s usually a disaster.

Fear of hiring is an appropriate fear because your unconscious knows that you’re not good enough.

Before you close your browser, spluttering in rage, let me explain.

An entrepreneur is not a manager

Entrepreneurs are smart, talented people. They usually rock at what they do. I’m awesome at un-picking complex psychological problems. The number two feature that I like about myself is my humility. You’re awesome at what you do, too.

But you’re not a manager. Unless you’ve been a leader of people in some other area, chances are that you’re a solopreneur who literally isn’t good enough… to manage a team.

Getting a team of people to do important work is harder than it looks. It requires a special set of skills that you won’t learn in school or from your parents. It’s tough and your unconscious mind knows this.

That is why your veins are riddled with fear. Your intuitive self is trying to stop you rushing into a situation that it knows you can’t handle. The same thing would happen if you lined up to ride a rodeo horse. Fear. It means there is something coming up which you need to prepare for.

This post isn’t about “how to be a manager” – it’s about how to pay attention to the signals your mind is sending you. It’s about how to overcome a hugely limiting form of self sabotage, that’s stopping you achieving your business goals.

If you’re a solopreneur who has always dreamed of building a team, it’s time to start preparing your mind for the challenge. You’re not procrastinating because of “control” issues, you’re procrastinating because you’re not ready… yet.

So get ready. Read, learn, train. You know how to be an entrepreneur. Now it’s time to learn how to be a manager.

Comment request for awesome readers: Let me know why you think you might be holding yourself back from growing. Also, if you’ve got any great management/leadership resources to read or learn from… share a link or tip!


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  1. Truer words were never spoken! I myself have recently taken a good long hard look at where I should spend the majority of my time, and outsourced my site design to the best creator on the planet (coming soon!).

    The amount of work I achieved in the meanwhile staggers the imagination. It was definitely well-worth the investment….

    1. Congrats Barbara! This (design) is a superb example of how online entrepreneurs can “let go”… and let’s face it, both your output AND your design are gonna improve! Win-win!

  2. *raises hand*… Can I ever relate to this one.

    I want the big firm and the big team. I grinned when you got to the part about being a great manager, because I know I’m that – I rock at bringing it all together for my team.

    And I need more staff. The fear? That I’ll never find the *right* people.

    I put out a job ad some months ago. I got hundreds and hundreds of applications… and didn’t find the person I wanted. It was difficult, stressful and disappointing. So I just don’t look anymore, because I expect a repeat.

    Here’s another fear: That I won’t be able to deliver on my promises. That I hire more team members to keep up with the work but that something (and I can’t even define what that something might be) would happen and the work would dry up. Then I’d look like an idiot.

    Another fear? That I’d have to work harder to make sure the team has more work than we can handle. That’s where we are now (because we’re awesome, ha!), but with extra staff, I’d have to bring on more work to keep their hands busy.

    And if I couldn’t, then I wouldn’t be delivering on my promises to those people, now would I?

    So. How about fear of the future? Not the success of it – the potential failure of it.

    Then there’s of course the need to find a clone of me. And that’s not easy, is it!

    1. They are some of the thoughts I had when I was about to embark on the solopreneur journey. Not about the staff obviously, but about the work.

      (And yes, you’d be very hard to clone James.)

    2. Hey James, I thought this one might itch!

      To be totally honest, I think that the whole “clone myself” cliche echos the fear of control concept I presented here. It’s not that you need to find a James-Clone… that’d be impossible.

      Instead, perhaps you need to figure out a way for your business to operate (workflow, management etc) that allows for scalability of a growing team of mere mortals.

      Now, that’s a total turn around for you guys… since every single one of your Men with Pens are total walk-on-water rockstars. However, it *kinda* is the secret to the whole Big Business dream.

      Figure out how to manage your business so that mortals can add value. At the moment it is *only* that “figuring out” which separates you from the owner of a ultra-elite huge big design firm.

      It’s not about control, it’s about business strategy.

  3. Peter,

    Most of the US businesses are small businesses. Every large US corp started as a small business. Yet, we do not teach our offspring to be entrepreneurs instead we teach them to be assembly line workers. Read, “Dumbing Us Down.”

    Good piece! Giulietta

  4. Is lack of trust considered a fear?

    As James mentioned, finding the right person to outsource work to looks like it could be a daunting task. However, if you ease into it with small projects you can find a compatible assistant or two.

    Giulietta makes a good point about public education’s anti-business bias. I have a son-in-law who has the talents to run his own business, but he is convinced that success lies in wasting more hours in the ivory tower and striving for a “job with a good corporation”. It took several years for me to banish that false belief… and I’ll not go into the rant I feel coming on… again 😉

    In the U.S., government is doing everything it can to suppress small business with insane employer/employee mandates and tax laws. These are huge drivers in the current trend to outsourcing and the growth of freelancing… and that could grow into yet another rant.

    My two centavos on a bright and beautiful day 🙂


  5. Hi Peter. Excellent article and I have to say once again, your WP theme is freaking awesome!

    This post is on target with what I’m currently doing. I feel like I’ve reached a max point of what all I can do alone given my time and other priorities/commitments. I recently hired someone from the Philippines to do some research and writing for me but unfortunately it didn’t work out.

    Now I’m looking more for that stay at home mom who wants to do a little writing on the side.

    But that’s just the first in my line-up of team members I have planned to create. I’ve got it mapped out as to who I need and what they will be doing, and that’s great. But honestly, what’s holding me back some is one thing… money.

    Baby steps… right?

    1. I’ve been watching you over the past few months, John (oooh!), and I have to say that you seem more determined lately to actually reach that success you want (and the one I know you can.) Taking more risks, pushing a little harder, getting savvier, getting a little more ‘come hell or high water’.

      S’awesome. *gives a friendly punch on the shoulder*

      1. Thanks James ‘ol buddy! Yes I’ve decided that it’s about time to stop the things that don’t work and do the things that do work and really focus. There are TONS of ways to make money online, but if you’re not focused, you’re going to fail because there’s just too much noise and you can’t listen to everyone. Pick the one or two winning methods that fit your style, make sure other people have made money doing it so you know it works, and dig in deep.

        And you’re right, I am very determined to make sure my financial success, future, and family’s dependency is not determined by some suit sitting in an office looking to make cuts.

        And honestly I have to say that a lot of what I’ve learned has come from that thing you call your brain.

        Oh yeah… “Hi Peter!” hehe Can James and I have a group therapy?

    2. Hey John, thanks for the kind words. The design is still making *my* eyes pop after all these months.

      It sounds like you’re on track for an empire. Hiring staff should be as self-funding as possible. If you can connect the dots between the tasks you outsource and profit margin, the risk becomes negligible. Then it’s easy to “just do it”.

      1. Thanks, Peter. Yup, on paper it looks easy… let’s hope it pans out that way. I think honestly that the hardest part is the hiring of the right people.

  6. Here’s my management/leadership tip.

    If your goal is to find good people, the example I refer to is what we learn when we want to purchase good stock. (I am not a financial stock broker, nor care to be, but focus on the concept).

    Correct me if I am wrong, but if you purchase good stock they will tell you it will go up and down depending on what the market does.

    Same thing, if you want good people, manage the environment. The only way to manage the environment is to know your people. You have to sincerely and geniunely care to get to know everything about them. Why?

    Let’s look at stock again…you need to know everything about your stock in order to know what things are happening in the market that will affect your stock. Right?

    How else are you going to make good decisions?

    Also, I agree, if you manage people, it is scary! I agree that’s something to fear. Why? What happens when someone tries to manage you?

    Manage is another word for control. Think about it and ask yourself if that’s not scary.

    But, then again, it might not be scary for everyone, which brings us back to caring to get to know your people.

    Did you say you wanted good people?

    Gotta care,


  7. Damn Peter, you are making me too self-conscious!

    The thing is, you’re right. If an entrepreneur wants their idea to grow, then they need to network with others and build meaningful relationship. It isn’t just about their genius, it is about sharing that genius with others and letting them be a part of it.

    I have to admit I suffer from this syndrome in varying degrees. I like to think it is about control. I don’t want others to “tarnish” my vision.

    But that isn’t how it works.

    Visions have to merge. It’s not about being “tarnished,” it is about seeing what other people see and working toward mutual goals.

    Hm…*thinking*…yeah, I got a lot out of this post. Thanks Doc. 😉

    1. Hey Steven, doc I am not – although I’ve been known to scribble prescriptions for things like “500mg of Keep-It-Real” on the backs of napkins and business cards.

      You’ve made some great points – I’ve seen many entrepreneurs hold on to “the vision” and prevent themselves moving forward. It’s always kind of ironic.

      It takes courage to expand your vision to include other humans. Have you got what it takes? 😉

      1. >“500mg of Keep-It-Real”

        Dang, that is a really strong placebo. Wouldn’t want anyone to overdose!

        >”I’ve seen many entrepreneurs hold on to “the vision” and prevent themselves moving forward. It’s always kind of ironic.”

        Yeah…you can’t know how the results will look until they are right there in front of you.

        >”It takes courage to expand your vision to include other humans. Have you got what it takes? ;)”

        I do, but I will also need others help along the way. And that is OK.

  8. Excellent post Peter (so good, that I think this is the first time I’ve commented even though I read them all).

    I’ve sort of come from the other side of the fence. I was a manager of a large team, and in the end I hated it. Looking back, it was because my team members ended up doing all the ‘fun’ stuff – and I would just get to manage them.

    So maybe some of the fear for solopreneurs is that they have to delegate some of the work they love too? In any case, I’m happy with my own company (for the time being….).

    1. Hey Sally! I feel all honored now that I got a comment from you 😛

      I think doing work that you love is a fantastic thing. For me, it’s obvious too: I’d never delegate the actual client interaction. However, we *all* have stuff we don’t love so much.

      Freeing up our time so we can do MORE stuff that we love. That’s the whole idea 🙂

  9. Thank you Peter for the article.
    It was timely as I’m just considering hiring a personal assistant, my second employee. My first hire was obvious. I have a radio show that needed producing, I found a producer. But this time is different. The thing holding me back (the fear factor) was lack of a clarity on what I needed – because there are so many potential directions for anyone I’d bring it next. What if I chose the wrong ‘next person’?

    I finally figured out the key criteria were: 1) versitility – could do multiple/various tasks and enjoy them, 2) drive – desire to step in/take on/help out, and 3) cultural fit -I’ve got personality and they need to like it. Yet as of this morning I was still on the fence. Then your blog came in my email. You had me think deeper and consider what my fear factor was…and helped me realize I have it handled. Thank you.

    1. Hi Kathi, welcome and thanks for commenting

      It’s fantastic that this post managed to come at the right time for you… a bit of welcome synchronicity is always good!

      Let me know how it goes with the new hire 🙂

  10. When I read the title of your post, I thought it would be about people who never go back to a 9-5 ever again, lol.

    The problem I’ve always have is that I don’t really want to be bigger at the moment. I don’t know if I’d define it as a fear exactly, but I don’t want to spend all my time running an agency, doing communication, and project management and no time doing what I wanted to do in the first place, which is work on client’s sites.

    That may be a whole other discussion altogether though.

    1. hahaha I can see how I lead you astray with that headline! At least you kept reading eh? 😛

      And yes, that sort of *is* another discussion all together. If you don’t *want* staff, it’s all good! But if you do, no more excuses for getting ’em eh?

  11. Hi Peter,

    I also see this pretty often: The entrepreneur who has a burst of self-confidence and goes out there thinking he’ll build his business… Only to come back a few months later wondering why this last idea also unraveled.

    While he does a few things really well, he just doesn’t ‘get’ that a successful business needs a full system.

    Doing a few things really well is only good if you work for someone else or have others working for you.

    Dov Gordon

  12. Another excellent, thought-provoking piece, Peter. Thanks.

    I know as I write this that I’m about to uncover a big piece o’ fear manifesting itself, but here goes: For our biz, it’s always about the cash flow. Managing people is one thing, managing that cash flow is another entirely….

    Maybe (maybe?!!!?) we manage our accounts poorly, but at any one time, we’re juggling multiple late accounts receivable, and there have been times I don’t pay myself. I bring people on for short-term specific project tasks, but even though we definitely *need* full-time help around here, and that person(s) would help us grow, the thought of adding a live human to our volatile cash-flow mix is scary. I keep saying “once we get ahead” we’ll add the staffer. Alas, your post reminded me (drat! ; -) we probably won’t move forward until we add the staffer.

    And there you have it.
    Keep it coming, Peter. I’m glued.

    1. Hey Keith, thanks for joining the discussion.

      Yours is a classic example of the point I’m trying to illustrate… but at least the SOURCE of your apprehension and hiring-fear is clear to you. You’re lucky – some people don’t have that luxury.

      Without knowing much about your business model, I’d suggest that you focus on finding staff to fulfill a role that generates postive cashflow for the business. I often recommend that the first thing businesses outsource is “sales”. This is often seen as dangerous, counter-intuitive thinking. All the more reason why it *works*.

      It’s definitely doable, and it could be done NOW… it’s just going to require you to do something you’ve never done before. The cool part? You’ll then get results that you’ve never got before 🙂

  13. This post is along the lines of the book “E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It”. Thanks.

  14. Wow, Peter, the timing of this post scares me! 🙂 I hired a Virtual Assistant a few weeks ago. A HUGE step for me.

    I’ve always said I want to remain a solopreneur and don’t want the baggage that comes with a large firm (that’s my OWN baggage form corporate life). However, I have recently seen than in order for me to grow the “vision” and efficiency of my company, I simply must outsource or hire on superstars. I really CANNOT do it all myself.

    This reality has whacked me upside the head and it scares the bejeezuz outta me. I’m now talking to some potential contractors and realizing I need to consider how that will change the way I operate–fast! But it excites me, too. I feel like I’ll no longer be handcuffed to the “in the weeds” tasks that keep me from moving forward. Plus, I also feed off of other people’s smarts and ideas. It occurred to me that hiring the right people could actually help define and tweak the vision moving forward.

    Thanks for the comment therapy. I needed to get that out!

    Fantastic work, Peter. Your blog really strikes a nerve for me on a regular basis. The sign of an EXCELLENT blog! 🙂

    1. Hey Deana,

      Thanks for the positive feedback 🙂

      I think theres a big difference between creating a corporate megalith of purposeless employees and building a nimble entrepreneurial team who do great stuff. The “all or nothing” approach of the corporate escapee turned solopreneur is a natural phase. But there are other (better) ways to do it!

  15. Pete – what a timely article. I was just talking to a client of mine about this today. Will offer out a tip to anyone who wants one. When my clients get overwhelmed and sort of go into “spinning their wheels” stages I want to stop it and get them back on track immediately. I have them spend a week creating a list of everything they do – from house cleaning to book keeping, designing, writing etc… everything. Then highlight the things THEY must do themselves, leaving a list of things you can hire someone else to do. Not everyone can afford to hire right away, or not all the positions that need to be filled, but at least you know where to start. The second thing I have them do is calendar everything they MUST do themselves first. Most people don’t realize that each time you are interrupted it takes about 20 minutes to get back to the place you were in your project before the interruption. I like to suggest people “chunk” their time to be productive. Once you get used to chunking, you will find you gain about 2 hours a day of wasted time. Whenever I feel off track, I do this for myself and often find a new use for another VA and then can hire them. As my business evolves, I sometimes find I am doing the new things that I can really job out – I find this exercise valuable to myself and rely on my calendar as my ” ideal self manager”……it always tells me what to do when and is so sweet about it! Hope some of you find this helpful!

  16. So, random twitter user here who followed a RT to your blog …

    And holy crap, I’m adding you to my Reader! This. post. is. amazing.

    So amazing, in fact, that I am feverishly writing up a new post for my blog to link people back here … I’ve been talking about this a lot lately for my readers; this theme, “Who must I become to complete this quest?” is coming up a lot in my work with clients, my own personal musings … this question has been such a driver for me the last six years, first introduced by my friend, Scott Jeffrey (

    I find myself “going here” with clients alot these days … sure we talk strategy, and we talk tactics, but the conversation that’s bubbling right below the surface, cloaked in raw vulnerability, is “the fear.” It’s moving, and such an important discussion because so many solopreneurs, as you call them, are going it alone, putting on a brave face to inspire confidence in prospective clients, knotted up inside for fear of being discovered a fraud, or of failing miserably, or of being rejected, or of letting others down. And in the next breath, shaming themselves for not being stronger or wiser or tougher.

    I recently created a blog to discuss 7 key shifts in entrepreneurial thinking that successful entrepreneurs know ( – and #4 is “Business owners need a tremendous amount of courage, and feeling ‘afraid’ is just part of your job.” And #5? – You must value your time differently and learn the art of LEVERAGE.

    “As an employee, you trade your time for dollars in a pretty linear way to make money. As an entrepreneur or independent professional, you soon learn that there are a LOT of hours that you could potentially work for which no one is writing you a check. Getting leverage is really the key to success in building a sustainable business — you need others to come alongside you as partners to keep things running smoothly.”

    Love your insights; you speak unadulterated truth, Peter, and it’s inspiring me to dig deeper, turn the mirror, see what else might be lurking. THANK YOU! 🙂


  17. Similar situation.

    I have work fluctuation so thinking to wait.

    I have several contractors and it was good experience.

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