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The Solopreneur Handicap That Makes You Suck at Productivity

If you can pull it off, being a solopreneur is great. You can create wealth and usually bypass the usual freedom-devouring traps that most entrepreneurs get snared in. If the goal is wealth, freedom and sanity… the solopreneur life is an increasingly smart choice.

Except for the side effect. Consult your entrepreneurial shrink first, because 90% of solopreneurs experience a severe productivity handicap. Here’s why the solopreneur life kills productivity.  The solopreneurial dream is sexy. Wake up at noon. Wipe last night’s cereal crumbs from your keyboard. Kicking off a day filled with social media buzzwords. Talk extensively about “shipping art”.

Ah, freedom!

Despite the obvious sarcasm, solopreneur life isn’t bad for those willing to make it work. The conspicuous absence of a boss telling you what to do… feels fantastic.

We’ve been so busy telling people to Escape Cubicle Nation, retire to 4 Hour Work Weeks and become Non-Conformists… that we’ve overlooked a few advantages of old-school big business entrepreneurs. The idea that small (minimalist) is good has been so fetishized that we’ve forgotten the original function and value of building something big.

Corporate productivity shits all over solopreneur productivity. 

I’ve got to be blunt, because I know you’re about to disagree with me. And maybe I don’t mean corporate in the worst sense of say, a GE advisory committee trying to make strategy decisions on microwave infrastructure and market demographic dynamics.

Yes, corporate bureaucracy sucks. Teams however, rock.

The original reason for putting a team together in a meeting room was to realize the vision of one person – the founder, CEO or manager. And, despite our desire to hate corporations and big businesses, this is still what happens in many many cases.

People get together, meet, make decisions and take phenomenal action.

Solopreneurs miss out on this and it really is a handicap. 

It’s been proven time and time again that social pressure boosts motivation. That’s why I always show up for phone consults with clients (they’d notice if I didn’t) but struggle to work on the sales copy for the new service I’m launching soon. One task has a huge component of social interaction and expectation. The other has next to none. Guess which gets done most consistently.

It boils down to accountability.

And, in the world of big business, teams exist to force mutual accountability on the individuals working on a project.

When a founding entrepreneur or CEO tells her marketing department she’ll have the plan for their PR campaign ready by Monday, you can bet it’ll get done. The CEO is accountable and experiences the pressure of the social dynamic. The team creates that pressure.

Do CEOs blow off commitments? Yes, but for every example of high level CEOs letting down their subordinates, there exists countless counter-examples in which senior execs step up their accountability in the face of a board of skeptical investors and advisors. Pressure and accountability can come from both above and below! Some might even say that public companies gain accountability and leverage via the social pressure of thousands of shareholders all looking for big results.

Solopreneurs want freedom from constraints, pressure and people telling them what to do. The problem is that they get it. Unless they figure out a way to stay motivated, they usually receive a healthy dose of poverty too.

While the solopreneur plays video games (or cleans his desk for the fifth time), the empowered big business entrepreneur and her team are kicking ass and taking names. They might not focus on “shipping art” or other lofty ideals, but they sure as hell get a lot done.

How can you be a solopreneur AND be accountable? 

I’m glad you asked, treasured reader, because I think in this case you really can have your cake and achieve goals too!

I was chatting with a client recently who’s experienced huge traction using Facebook’s social accountability plugin. It turns out, if you have a good network, there are plenty of people interested in holding you accountable to get things done.

The evolved version of this strategy is one I recommend to clients: Build an advisory board. 

Consider formalizing your relationship with the people (friends/family) who are stake holders in your life. The people who care.

By creating an advisory committee, you can check in (monthly or quarterly works best) with a team of people who are focused on your success. For an hour a month, their job is to hold you accountable to your promises.

Solopreneurs need this. 

We need to create structures in our lives that force us to make commitments. We need to be held accountable. Most of all, we need to have the foresight to set up these structures before we really need them. And, we need to ensure a structure like the board becomes autonomous enough (how awesome are your friends?) that it effectively “catches” you when you fall.

As a solopreneur, you should be accountable to your “board” to follow up and report on last quarter’s game plan. After month one, how far along are you? Have you shipped what you were supposed to? What obstacles did you hit? What did you learn?

None of these questions are rocket science, but they are the sort of thing someone else needs to ask. And sure, having a great coach (just click here) is a great first step… but the power of an advisory board should not be overlooked.

The best part is that you don’t need a table full of business gurus. One or two help (coaches make great board members) but there is actually a huge benefit in having a few “civilians” on your team too. Non-entrepreneurs who nevertheless care about your success will swallow less of your BS and be more ruthless in holding you to your ambition. Your 9-to-5 friends believe you’re a slacker anyway, so having one on your board will ensure high expectations for your work output. The truly brave will invite their moms to the table!

An effective advisory board will hold an entrepreneur to: 

  • Develop, present and lock down a specific business plan. No more changes in strategy every two days – if you want a change in direction, present your case at next month’s meeting.
  • Connect the dots between long term vision and day to day action. Want to write a book by the end of the year? Your board will figure out that that requires 500 words a day, starting today. Present 15,000 words at next month’s meeting or do not pass go.
  • Manage your Cashflow for real. Present your budge, P&L and expenses to your team. Want to blow last month’s profit on new Apple gear? Your mom (and the rest of the team) might have a different idea of where to “invest” those dollars.

… and so, so much more.

If you’re feeling the uncomfortable realization that you need this type of accountability in your life and business, you need a board. All of these accountability factors are a given and total no-brainer in larger businesses. Big business entrepreneurs shoulder this kind of healthy pressure daily.

That’s why entrepreneurs achieve such huge things.

Solopreneurs have a productivity handicap. Entrepreneurs with teams are much more effective because they’re accountable to others to get things done and make good on their promises.

It’s time to shift from solopreneur to the real deal. Assemble your board and get ready to commit action.

Leave a comment and let me know your thoughts…


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  1. Alright, I absolutely agree with some parts of this and have thoughts regarding others.

    I agree that working in a team is highly motivating, work gets DONE and when you can’t do all the work yourself (no solopreneur should), you have a team that helps you move the project from idea to completion faster. Awesome.

    I also agree that larger businesses increase productivity. Because Paul in R&D is waiting for your report, you actually write the report. You can’t walk over at the end of the week and say, “Sorry, I blew this week – got stuck on Twitter and now I’m just behind.”

    As a solopreneur, you need discipline. (This is why I went skiing with my children yesterday on Sunday and blew off the day with them and why today, on Monday, during their March break, they have to wait until my work is done before I can come play – otherwise, it’s just too easy.) You have to replicate – alone! – a corporate environment that gives you structure and productivity.

    But I’m iffy about the ‘accountability/deadlines’ aspect. Mostly because nothing would derail me more than that. Having someone tell me, “James, you didn’t do XYZ this week,” makes me want to respond, “No, I didn’t, and I don’t need you to tell me. I wasn’t lazing around, though, so bugger off.” 🙂

    So I guess what I’m saying is, I love the brainstorming/help me potential but dislike the you-were-a-bad-boy aspect. And for that, the very concept of accountability isn’t one I warm up to. I *resent* it.

    Though perhaps that’s because I define accountability differently than what I believe your post outlines. And on that thought… time for more coffee. 🙂

    1. Heya, I’m not sure you’re quite on the same page with what I’m saying here… it’s not really a “bad boy” thing. But, I also think that your resistance to that idea is the perfect evidence that you probably need it… or would benefit massively from it.

      If I was on your board, I’d want to know what you were doing when you “weren’t lazing around” 😉

      But then again, maybe that’s all a bit too uncomfortable! 😛 😛 😛

  2. Hi Peter

    Great post and great response from James. Definitely resonate with the resentment aspect but really that is only because for me accountability is super-imposed with authority/control.
    I’d make a great Advisor because when reading this when not relating it to me its so damn obvious.
    Caring Accountability with the Intent that You Achieve Your Goals is what it is all about.

    Thanks for the words.
    (is it good to be ‘home’?)

    1. Hey Bonny,

      This is exactly it though… as entrepreneurs, we WANT freedom from authority and control to the extent we often won’t even take control of ourselves. That’s why this is so needed.

      Remember when YOU ask a board to hold you accountable… you’re in control because you’re initiating it.

  3. I came across a quote from Andy Warhol that I think might resonate with the core of this post:

    “When I think about what sort of person I would most like to have on a retainer, I think it would be a boss. A boss who could tell me what to do, because that makes everything easy when you’re working.”

    Another thought that halts me in the tracks of solopreneur-dom is something that was asked by Argentinian entrepreneur Martin Varsavsky:

    “How different is your life from that of a prisoner in a jail with internet connection?”

    It is scary how many days my answer can tend to “No different.”

    Thought provoking post!

    1. Ha, Conor… I love that quote. So damn true for me, so many days. At least my jail cell (Manhattan apartment!) is quite nicely furnished and close to some good amenities 😉

      Warhol got it right though. That said, NOT having the constraints of someone telling you what to do is what enabled him (and enables us) to create art. The purpose of the board isn’t to be told what to do… but to make a commitment to actually DO what we want (as opposed to just thinking about it).

  4. I think I may know where James Chartrand is coming from.

    I absolutely loath criticism.

    If I make a mistake or fall short of a commitment, I will have beat myself up 10X more than anyone else would ever do. I’ve also moved on before any external criticism arrives. So someone else adding to that always feels like they’re maliciously salting the wound.

    As I read this post, I started to try and figure out which of my friends I could tap for this role.

    Because of the way I am so overly sensitive to criticism (and I am) it takes someone who can deliver it in a specific way. If I like and trust that person and they can deliver it in a way that I don’t feel like I’m being talked down to, the message gets through. It always has.

    I worked for a Fortune 100 company for 15 years and was amazed how some of my supervisors could magically bring out the best in me while others seemed bent on tearing me down.

    The one thing I noticed was that the ones that were “bad” gave me feedback in a way that seemed like they were using a ten pound sledge hammer.

    The “good” ones had a very smooth touch. They held me accountable in a way that didn’t trigger an angry response from me and always seemed to leave me feeling like I really did want to rise to the occasion and do even greater things.

    The bad ones made me want to dig in me heels or just quit (which I eventually did).

    So I find myself with a very short list of only one person who I know can fully hold me accountable but not in a way that will just cause me to buck the feedback. And interestingly enough, that person is already doing it, I’ll just need to formalize it a bit.

    -Richard Lee

    1. I think it’s more that I feel someone saying, “You didn’t get that done? Well work harder! Do it, dammit!” is pretty useless feedback. If I didn’t get it done, there’s a reason for it, and it seems more useful to me to explore the reasons WHY it didn’t get done, and how to fix that.

      Was it because deep down, I knew it wasn’t a good idea or the best investment of my time? Was it because I literally didn’t have the time? Was it because something else is blocking my forward progress? Eliminate the obstacles to efficiency and production – an ass-kicking doesn’t always do that.

      Now, an advisory board, someone who can say, “Okay, cool – looks like you’re stuck here… have you tried this? thought of this? what about if you did this instead?” makes FAR more sense.

      (Which might actually be what Peter’s saying in this post.)

      1. I agree with James about how asking why I didn’t get something done is far more useful to me than just telling me to do it. I’m quite motivated and I believe we all are. I would love to meet my goals. If I don’t, there’s something amiss and I don’t need to be berated for it.

        I’ve dreamed of a team approach to my business for a long time but I have yet to find good candidates for the team. Within my social circle, my entrepreneurial dreams are unusual and most of the time, misunderstood. I’ve learned to keep a lot to myself to avoid getting comments that shake my confidence. None of my business colleagues want partnerships (on any level) or have proven to be unreliable partners.

        But your article has renewed my desire for a team, so I’ll keep my feelers out.

        Thank you.

  5. try using software to help you. For instance I have a program called Freedom that locks me out of the internet (Cost $10). I have another program called ‘write or die’ which is used to set writing time and word goals and it knows if you aren’t typing and plays unpleasant sounds or gives warnings to get you back to work (also cost $10).It also has a setting where you can compete with someone else writing on another computer on-line. These are obviously solutions for writers but could be used for non-writers.

  6. Seriously good post. This has definitely become my struggle. I thrive and get ridiculous amounts of stuff done when I have to. But it does become very hard to continue on a highly productive pace once my initial excitement wears down.

    Thanks for the encouragement to set up a board.

    I’m looking forward to regularly gleaning from your site.


  7. as a consultant, I had a client suggest this (she learned it from a seminar she went to in Boston last month). And asked me to be a part of her Advisory Board. I am honored and am glad to have read this article, I was weary of her concept, now I get it. I have talked to many folks who want to create a monthly “Networking” group or a Quarterly “Women’s” group or a Weekly “Sharing” group, you name it and people want to get together, but I have held back from joining or creating any, my time is valuable and I want the time spent with others in my community to be be highly useful and productive. This advisory board sounds…….Useful…… I’m on it! With this and her information I believe I have enough information to roll forward with it! Thanks for the clarification!

  8. Great post Tanja,and I love your quick n’ dirty details soiectn very cool! Your new website is so lovely and inviting, huge congratulations and wishing you a wonderful close to 2012 and a truly fabulous 2013 xxp.s. counting down the weeks now until we fly over to NZ for a month long visit with hubby’s family can’t wait x

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