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How to avoid the traps of Solopreneurship

This article isn’t for my readers who’re tycoons with empires. Or even those of you rocking small businesses with growing teams.

You people should tune out right now, because the solopreneurs and I have some highly classified information to discuss.

Listen up solopreneurs. I’m talking to you. You’re running a very small business – probably from home – and you’re all by yourself. It’s not easy. In fact, you’re exposed to all kinds of pitfalls other entrepreneurs never even experience.

None of these rusty bear traps are too scary if you know where they lie. But i you aren’t clue up, you’re at serious risk – your small business could be utterly derailed by any of the following three obstacles…

1. You don’t know the definition of “Enough”

The great thing about having a job – something you can probably remember vividly – is that you clock out at the end of each day. Even if you work late, you still get to shut down your computer and go home. Pour yourself a drink and put your feet up because work and it’s concerns are done for the day.

Remember those glorious days? As an solopreneur, your work station is probably less than 50 feet from your bed and it shows. You have the freedom to work from anywhere, anytime you want. Problem is, now you feel like you have to be working.

From everywhere. All the time. Work is always on your mind.

It may even keep you up at night.

There’s no boss to hand your report to on Friday as you dust off your hands. Your to-do list doesn’t end at Q3, and there’s likely no end in sight of the project you’re currently working on. And worse, there’s a guilty feeling at the back of your mind: whenever you do anything, you should probably be doing something else.

Knocking off at the end of the day is hard, because every task you check off your list just spawns another few in its place. There’s no end. You can never do enough, and everything could be better.

If you’re a solopreneur, you’ll drive yourself crazy striving towards perfectionist ideals of “enough”. You’ll massively overestimate what you’re capable of in a day. Then you’ll almost kill yourself trying to get there.

Every solopreneur stumbles into this trap, without fail. If you think you’re somehow different, you’re being hopelessly naïve.

The solution is simple, but you can’t just leave to chance. You have to put in daily effort and make it a habit:

Predefine what it means to “do enough” so you know when to finish your day.

Your sanity will thank you. 

This is harder than it sounds. Doing it tomorrow is easy but it takes discipline, self awareness and relentless commitment to make this happen everyday. And it’s everyday that you need it.

You need to decant your massive to do list into a daily list that answers the following question:

“What do I need to do today to consider the day a big success?”

Answering this question gives your unconscious mind criteria for “enough” to work towards. It’s the key to clocking out every day feeling like you’ve moved the ball forward rather than just drowning in more work. You’ll accomplish better work-life balance, and in turn discover the key to sustainable success as a small business owner.

2. You’re isolated and lonely

This one requires very little explanation.

As grown adults, our number one source of social interaction is the office “water cooler”. People tend to hang out with their work colleagues, especially if they’ve moved from the place they grew up and went to school/college.

When you make the decision to be a solopreneur, you’re basically cutting yourself off from a regular social life. This is dangerous for a number of reasons.

We need social interaction just to keep ourselves happy. We’re social animals at our core. Beyond that, friends are really useful for a few things when they’re conveniently nearby:

Solopreneur isolation tends to creep up on you. You make an effort to network and for a while that satisfies your social needs. Then, you tell yourself it’s time to seriously “buckle down” and get work done – so you dive into a week (or more) of nonstop heads-down work.

This is when isolation strikes.

An entrepreneur with a team – or even a regular employee – will still interact with a ton of people, even if they’re scrabbling on an urgent project.

As a solopreneur, socialization won’t find you by accident. You need to have a plan to make it happen each and every week. Investing serious time and energy into building your network – with socialization and fun for fun’s sake as goal – is the answer.

3. You’re riding a financial roller-coaster

The biggest problem with solopreneurs is that they perform the psychological miracle – or perhaps schizophrenic nightmare – of being both product delivery AND sales departments. In the same person.

… But not at the same time.

In even the smallest startup, there is a virtual line-in-the-sand that divides the office between people responsible for sales and business development, and the folks that do the actual THING that people buy. They’re different roles with vastly different skill sets.

And you’re trying to do both.

First of all, know this: You are doing it right. 

It’s impossible to grow an empire and build a team without having real world experience in both sides of the business trenches. You need to build your thing AND you need to sell your thing. And you need to do customer service for your thing. It’s all good.

Just know that the internal dichotomy you’re wrestling with isn’t supposed to be easy or even remotely sustainable over the long term.

The financial roller-coaster happens because of the up-and-down bottom line performance of solopreneur businesses. This is caused by you, the founder, working as a sales person and then having to stop selling the moment you sell something.

Problem: You can’t keep selling, because you have to rush to deliver to your new customer. 

This is the devastating trap for solopreneurs: Success itself actually prevents you from growing, by tying up your time as you service your newly found customers.

It’s sometimes difficult to spot the symptoms of this problem when you’re deep in it, but if you’re a solopreneur who seems to magically always be busy half the time… then furiously hunting for work the other half… then this is you.

The solution lies in innovation and leadership. No big deal!

To push through this ultimate barrier to growth, you have to figure out how to leverage technology or people to get to the place where you can keep selling even after you’ve sold. 

Read that again: You need to keep selling even after you’ve sold.

This is the golden rule that will elevate you beyond the pitfalls of solopreneurship. And interestingly enough, it’ll also result in so much growth that you won’t stay a solopreneur for long.

There’s a few nasty chicken/egg type situations you need to figure out before it can happen, but never forget this one thing:

Your objective is to build a business where sales and marketing happens daily. This is the only way to get off the solopreneur revenue roller-coaster.

Exciting news for solopreneurs wrestling with this stuff: A solution is on the way. I’m about to announce something new and cool for solopreneurs who are ready to solve these issues once and for all. Stay tuned.

It’s the first time I’ve ever created something specifically for solopreneurs ONLY, so if you are one you’re going to want to know about this.

This list of three is far from complete. This is just the problems I see solopreneurs struggling with the most. What have you observed? Share your additions to the list in the comments below – there are no wrong answers, because we all learn from your experience.


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  1. Hi Peter, this list is right on target. The isolation and loneliness really caught me by surprise. Yet, I feel guilty when friends invite me out and I think I am wasting time.

    I don’t know. It’s hard to say that our “enough” is ever enough especially at the start when we are so prone to procrastinating and doing random stuff instead of focusing on the big wins… I mean I’m sure you do more in an hour than many of us do in a day, which is why we have to hustle more. At least until we get to that point.

    1. Hey Chiara! The guilt issue you mentioned is all too common I’m afraid – that’s why getting that definition of “enough” is important…. so that you can give yourself permission to prioritize socialization and R&R.

      The thing is, most people are only good for a few hours of ultra productivity per day anyway – regardless of how experienced they are. So working hours upon hours isn’t winning anyone prizes.

  2. OUTSTANDING article that’s spot-on! I have had the good fortune of being a solopreneur for the better part of the last 20 years and it’s taken a lot of trial & error to get it fine tuned. I WOULDN’T trade it for anything…

    1. Hey Michael,

      I just ran across your comment from way back in September of 2013 and I wanted to ask how it is still going for you as a Solopreneur? My biggest issue is that whenever I have a demanding project, I cannot continue to fill my pipeline.


      ~ Jacqueline

  3. Peter, if I may comment on item one: two things that have worked for me in the past. One is setting a time to knock off. This is especially good when you’re overwhelmed with things to do.

    Second thing is instead (or in addition to) a to-do list, keep a “done list”. This is a trick I learned years ago when I was constantly overwhelmed. I simply set a pad of paper next to my computer, and every time I got something accomplished, I wrote it down. It turned out that I was getting a hell of a lot of work done each day, but it took keeping a done list for me to realize it.


    1. The done list is a great tactic Mike. One that I use myself. I know I can beat myself up about the huge pile of yet-to-be-done items (never seems to shrink!) .. and the done list tactic is a panacea for that. Great tips!

  4. Right on!
    Aloha Peter!
    I am pretty much happy with “good enough” (parenting and helped learn that one) especially as new skills need to be constantly learned in this fast paced e world.
    For me the biggest difficulty is in switching back and forth in-between online marketer and coaching or consulting. These tasks have very different skill sets for me and I often want to stay in one mode or the other if I am in a good flow (or if it’s a tough day I want to run away to the other). Many days I am switching back and forth due to appointment times and can feel I have not transitioned back and forth gracefully.
    Great post, I suddenly feel connected to something out there in the ethers for some odd reason.

    1. Hey Gina!

      That switching back and forth is the precise cause of the financial roller coaster – a bigger company would have dedicated staff on both sides of the office. Getting your schedule organized so you can really get into the flow of marketing will be important – if you’re good at the coaching work you do it’ll be easier for you to jump into that at a moment’s notice.

      1. Gina and Peter and Mike…great, helpful comments. I think I may have fallen into the trap of saying yes to a lot to keep busy with networking, add a credential, demonstrate leadership….but it speaks to the point about making sure I don’t face the isolation which I believe would paralyze me entirely….I am just starting and blocking my schedule is my new,old biggest challenge!

    2. Gina,

      Do you schedule coaching or do it on the fly? I find that scheduling client calls (for services), as opposed to just taking them as they come in, makes a big difference.

      Also, it wouldn’t kill you to not take incoming client/service calls at certain times during the day or week. When I was in the corporate world, I would turn my phone off for three or four hours a day in order to get my work done.


  5. It’s like you were reading my mind. I think my biggest pitfall is number 2, the isolation and loneliness. I have had a hard time finding “real” people who relate to what I’m doing in my business because they don’t even understand what an internet business is.

    Then I have a hard time finding people in the online world who I relate to because I am a mom with a very young family and most internet entrepreneurs I have met are men (and of most of them don’t have children). Quite often what works for me is completely different than someone who is single or does not have kids.

    Additionally, I stay home with my kids during the day and work at night (or in the early morning). So when I get done working, I still have to work. The isolation and loneliness is made worse because I spend my “free time” alone with two kids instead of with grownups.

    So when I finally decide to decompress I am faced with the guilt of feeling like I haven’t completed enough in my business, as well as the guilt of giving up time with my family to do something that is fun just to make myself feel better.

    Then, quite often I choose to be by myself because I need time by myself to re-energize and also because no one in “real life” gets what I care about anyway and talking to them can be more work than fun. This drives this destructive cycle even further.

    Can’t wait to see what you have in store!

    1. Hey Missy – so glad you pointed out the extra layer of isolation this whole internet thing adds. It’s so true and I’ve certainly felt it in some places. Geography has a lot to do with this one as there are some places internet people congregate. Get thyself to some conferences!

      Stay tuned 😀

  6. As a small business owner who has business on the brain 24/7 – the ‘enough already!’ point is the one I’d love to nail! life can get out of balance quite quickly.
    My isolated barometer lights up when- I tell myself jokes and laugh at them !

    A water cooler where we can connect with real business owners who are soloists sounds great – real connections with people who ‘get it’ can make a great difference.

  7. Thanks Peter,
    You’ve hit the nail on the head with those top three. It seems that the question of not knowing when to call “enough” tends to lead to isolation, and that the financial roller coaster prompts the fear based motivation to do more – a vicious circle that has got us solo-preneurs by the short boot-straps.

    One of the tactics I’ve come up with in the last couple years has been to take some of my branding services and turning them into products that sell digitally (design templates and branding tools). This has helped quite a bit with reducing the extremity of the bumps on the financial roller-coaster of solo-preneurism – and yet fueled even more ideas and ambition that falls into the “when is it enough” category.

    Part of the step needed to get out of the vicious cycle of those top 3, is learning how to let go enough to hire help in the areas where I’m not so stellar (regular book-keeping and a social media/marketing person). Issues of trust and the belief in one’s own ability to generate enough income to support not just myself but contractor’s fees is a scary step. It also challenges some limiting beliefs about the right we have to scale and play bigger. This would be an awesome area to learn some tactics for growing my business beyond the 18 hours I have each day with my peepers open.

    Looking forward to what you develop for us solo-folks…

    1. Hi Amy,

      This is a fantastic comment – thanks for the insight. You’ve homed in right to the sweet spot that interests me most: Where a solopreneurs self beliefs affect their ability to scale.

      Thank you for this!

  8. I wrote into Peter directly on this one because it was so right on, and just wanted to take a moment and say something to the community here.

    This article hit the nail right on the head… now 3 and 1/2 years into my solopreneur venture. This is exactly the biggest challenge and split that is causing me an up and down financial rollercoaster I want to get myself off of.

    For me I have some health issues that have played into this I’m working on to get stabilized. I notice that when I take really good care of myself and feel solid, confident and stable it is much easier to manage my clients and keep my income more stable consistently.

    After I get through “the woods” of my caffeine/sugar addiction transition and more stabilized, I look forward to learning how to grow past solopreneuership so that the sales can stay ongoing while I get to do what I love out in the field!

  9. Wow, What a great group. I totally relate to what Brian and everyone else has said. It is good to know that I am not screwing up all by myself. Just found this site and downloaded the ebook. Would love to read it right now, but need to get some billable hours in…

  10. Hey Peter,

    great article, though my experience with solopreneurs has been to direct them toward at very least building out a team they can draw on. The true adjusted success rate of going it solo is so incredibly low that I would simply not recommend it of any of my clients or students.

    Now, that said, I believe there is a big difference between an entrepreneur and a business owner/operator. This seems to have been lost in the most recent 10 to 15 years with the tech start-up craze, but by definition, a business owner is not necessarily an entrepreneur, solo or otherwise.

    Those that do against all the best of advice of international business coaches, mentors, authors, and whatnot should at very least be connected into at very least one great mastermind group. I don’t mean those cheesy local business networking groups that are sorry masks for business card pushing, I mean a real mastermind.

    Perhaps find an entrepreneur group on or the like, or even on Facebook groups.

    In the end, chances are, there are many hats that the individual is ill-suited to wear, but many of them wear all the hats nonetheless, to the detriment of their business’ success, their family life quality, if not their own sanity.

    Solopreneurship is a challenge that is totally unnecessary, and very risky on all planes.

    Some of my most successful clients started out as solos, and took on one or two key partners to advise and share responsibility, only to see their ventures finally get the wings they wanted.

    Again, great piece.



  11. Solopreneurship is definitely not fun!
    It’s physically, emotionally, and mentally exhausting. I agree with the isolation thing. It’s slowly eating you up, sometimes hampering you of productivity.
    I think solopreneurs must get rid of that superhero syndrome NOW.

    Great post!

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