What Keeps You Awake At Night, Entrepreneurs?

These are the burning issues I am hearing recently that are keeping entrepreneurs awake at night:

  • Social networking confusion: so many sites, so little time. How do you tell which ones are worth your while?
  • Google Ad costs rise: as more big companies turn to search marketing, smaller businesses are feeling squeezed out of the search ad picture. Per click prices keep going up up up.
  • The stock market: Retirement portfolios were doing great since April. But last week saw a lot of those gains disappear when the market went south. The scuttlebutt I am hearing is ‘how will we ever prepare for retirement?’

What’s keeping you awake at night in your business? What’s concerning you right now?

Leave a comment and let us know.

UPDATE:  the conversation is continuing over at LinkedIn, where I asked the question using the LinkedIn Answers function (which works great, by the way).  As of midday on Monday July 30, there are 14 excellent answers on LinkedIn Answers. 


Anita Campbell Anita Campbell is the Founder, CEO and Publisher of Small Business Trends and has been following trends in small businesses since 2003. She is the owner of BizSugar, a social media site for small businesses.

21 Reactions
  1. What I wonder about is all these new social bookmarking sites. If someone bookmarks my site is that the same as me creating a backlink to my site? How many bookmarks does it take to boost google pagerank in comparison to links?

  2. Plenty keeps me awake: the unpredictable revenue of an early stage B2B company; the uncertainty around raising the $1 million I am working on; the latest Harry Potter book (I really have to get some sleep); and my two small children.

    Some insomnias are better than others!


  3. Hi Anita,
    What keeps me awake at night is something that is close to you….
    The future of Cleveland, Ohio…
    There is always some positive stuff to talk about, like the really smart local technology people that ARE staying here, and trying to keep the tech part of our area up and running, and are adding new innovative things to web 2.0 etc.
    On the other end, we have old school politicking still going on, and nothing is really changing in downtown Cleveland. So, in summation, what keeps me awake at night is our local scene, and what is in our region’s future?Or are we just..well..done?
    Joel Libava AKA Franpro

  4. Taxes. Wouldn’t it be great if we (businesses) didn’t have to be a collection agency (for little or no compensation)? The cost of doing business just keeps rising…

  5. I’m apparently cyclical. I worried a lot about social equality and distribution of wealth as a college kid 40 years ago and I didn’t have time for that while building my business. Now the business feels solid so I do again have time to look beyond it and I’m worried about the world we’re passing on to our grandchildren.

    And as soon as I say that I come back with a shock, and fear, as soon as anybody starts thinking business is solid and there’s time to worry about something else, that’s complacency and tempting fate. I just knocked on wood. So looking at business worries, my business worries have always been cyclical too, know that I think about it. When cash is short we’re probably growing so it’s a matter of managing working capital, and if cash is good then I’m worried about what we don’t see, just around the corner. What’s out in left field where we can’t see it?

    — Tim

  6. well, i own a staging company that stages home for sale. :: BIG sigh :: Like ProfitTheme, a lot keeps me up at night. Mainly 1) consistent income and 2) building reliable team (both my assistants are moving out of state next month). Both of those involve a lot of work and planning and mostly trials by fire! Which is really hard to juggle when I am a one-woman company.



  7. hello!!!

    The rising inflation level is tingling me a little.. The reason being unequal distribution of income is causing the society to split in two halves…

  8. Graham Lutz, The Young Capitalist

    I’m worrying about how to comw up with new ideas…

  9. Elizabeth Partin

    Hi Anita, I worry about diversification. My business is exceeding all of my performance measures and goals, but…….50% of revenues are coming from one client. I know this places me in a vunerable position, but part of my measures includes the amount of time I spend working and the amount of time I have available for the rest of my life. These work/life measures are as important to me as revenue measures. If I go after more business (and get it) then my other measure begin to suffer. I realize this may be a nicer problem to have than no clients, but right now this is what I have been stewing about.


  10. Hi Anita, we asked this same question to dozens of small business leaders/CEOs…and of course, their answers ran the gamut from:

    • Communication — employees lack clarity and direction, limiting innovation and results
    • Accountability – measurements of and responsibility for results are insufficient
    • Engagement — people don’t seem to care as much or aren’t sure of their role within the company
    • Alignment – employee activities aren’t connected with organization mission and strategy
    • Direction – disconnect between planning, strategy and execution
    • Transition – a desire to “pass the torch” successfully
    • Control – things “feel” out of synch
    • Frustration – excessive friction in daily work
    • Risk Management – profit variability versus growth rate

    These were the things keeping CEOs awake at night.

    Interestingly, the real challenge is helping these CEOs realize that their particular challenge at the moment is a symptom of a deeper need all growing organizations face: the need to systematically increase the capability of their organization to address future challenges.

    Years of research like this revealed to us that successful businesses all follow six fundamental disciplines related to: strategy, planning, organizing, executing, measuring and learning. Our program uses a holistic approach to instill all six of these fundamental disciplines into the activities of every employee, every day. Simply put, Six Disciplines improves an organization’s ability to plan AND execute better—in a systematic, enduring way.

    All the best!


  11. I do not own a business, but would love to do it. I worry about my family, insurance and coming up with the right idea … that keeps me up at night sometimes.

  12. How to keep orders more consistant…

  13. Wow – keep em coming! These are important issues. It gives me some comfort to know I am not alone and that others share similar issues.

  14. How can I create more differentiating value to become their natural first choice?
    How can I increase my profits with a premium version of my product/service?
    How can I increase my retention rate of current clients?
    How can I increase per-client spending?
    How can I motivate my clients to refer more and more qualified prospects?
    How can I enter lucrative, new niche markets?
    How can I reduce my overhead without reducing the quality of my product/service?

  15. Low cost competition especially coming out of China and Eastern Europe is starting to become a concern for many small businesses. Not only do they know little about these sources of competition but the internet as a means of reaching the local market, albeit in in a small way, means that they can really start to capitalise on their low cost base.

    Quality and reliability used to be an issue but this is disappearing quickly and the pace at which this is happening is quickening. It is the competition that they did not see which is a big worry for these entreneurs

  16. Hi,

    What keeps me awake is :

    How to get my simple books read by more, as it saves thousands of man hours, and save precious time for all ?

    How do i tell people that, our books will get you start developing a commercial software in a few hours !

    How do i tell people that, we do not teach you using wizards, which are misleading to say the least.

    How do i tell people that, stop buying expensive software, instead read our books and develop our own.

    How do i tell students (and their teachers) that software development is a hands on skill, and there is no use unless you can do it on a PC.

    How do i tell people that we are genuine and not a fly by night operator.

    How do i tell myself that this is a worthy thing to do, authoring/self publishing for life…

    How do i get a few well wishers who can offer a link to our site or a review…

    k r i s

  17. Business Advice

    I often find myself in a situation where I feel things start to get intangible. Business, life and everything else. But in these situations I usually just spend an hour or so in order to simplify everything in my mind. Because, by the end of the … night … it’s very easy to simpöify everything, once you believe you can do it.


  18. as an pre-launch web software co., I worry about getting the word out to my customer base, and acquiring those first few customers that will get us moving in the right direction. We are building it, but will they come?

  19. The many risks that you dare to take.

  20. Information overloaded, tons of useless information was spammed through out the whole internet, user was wasted a lot of time in searching for rubbish rather than the actual info they want. To create a website which valued for others is my concern.