What To Do When Things Aren’t Working Out

Working out

Shit happens.

As an entrepreneur, it’s inevitable that things aren’t going to work out as planned. Just because you came up with the idea, doesn’t mean it will work.  That would be like working out at the gym and thinking just because you put the weight on the bar, that you should be able to lift it. That’s not how it works.  There’s a point where the weight is too much and you’ll fail to lift the bar. Now, that doesn’t mean you’ll never be able to lift that weight, it just means today you can’t – you’re just not strong enough, yet.

So what do you do when this happens in your business? When you’re trying to manage more projects than feasible, and worse, your not seeing the progress you want?

Here’s what I do when this happens.

1. Revisit my “Why”

If you don’t have a strong “Why” for building your company, then start there. If you forgot your “Why”, then revisit it and ask if you’re still on that path. Many times entrepreneurs start of keen on solving a certain problem, for a specific customer in a unique way – but for one reason or another – things don’t pan out, so they pivot. The risk is you pivot out of your passion. Then one day you realize your building a company that you aren’t excited about.

So stop and re-align.

The #1 energy source for entrepreneurs is their passion for the business. It’s why 2 guys in a garage can compete against a fortune 500 company with unlimited resources. They have so much passion, that they won’t give up when any normal person would. That needs to be present, or everything else just won’t work.

2. Do less

Many times, entrepreneurs get to this point because they have too many irons in the fire. My advice is conduct an audit of all the initiatives and projects your have going on in your company, and prioritize and kill the bottom half. It’s always better to put more wood behind fewer arrows, then to spread yourself too thin. Doing less is o.k. Just do less at a higher quality. Make it your best work.

“.. more companies die of indigestion than starvation”

Bill Gurley

I probably reasses 5 times a year, where I sit down and review all of our projects and ask – what’s really important to get right? What’s noise or “busy work” that won’t create a better experience for our customer? What am I working on that is for pure ego? (yep, I ask that – cause we all do it). It’s hard to do. Most entrepreneurs have this tendency to create work, as that’s what they do best, creating. But sometimes you need to stop building, and ensure the things you’ve built is delivering the value to the customer you expected. Many times you’ll realize they’re not.

3. Become a secret shopper

When’s the last time you used your own service as a new customer? How does that process feel? I usually spend a week every 3 months improving this process. Every new customer / lead / prospect will go through this process – so it needs to be rock solid. Become a “secret” shopper – signup or use your company but don’t tell your team (or have a friend do it). Experience your service from their perspective. If you have dozens of different types of customers, re-read step #2 :). Figure out how your message is being communicated on your website, write down all the things that are broken in your on-boarding, and see how responsive things feel. Were you delighted with the experience? If not, fix it.

Business thrive on 2 things; 1) Retention – do you customers that buy, keep buying, 2) Profits: are you making enough profit per customer to re-invest in the business to grow. If you don’t have those, stop and fix them. Many companies operate at a loss, or essentially work for $9/hour when you calculate all the cost involved in getting new customers and delivering the service. Or worse, never have a customer buy again or recommend a friend. This means you need to keep acquiring new customers every few months JUST TO GO SIDEWAYS = no growth. Run the numbers. Be sure that you’re actually building a business, not creating a low paying job for yourself.


That’s all I’ve got.  I’ve worked with many entrepreneurs thinking through each one of these  buckets, and it’s always helped them get out of a rut.

Just to recap:
1) Ensuring your hearts still into it – and if it’s not – fix that.
2) Make a list of all your open projects, commitments and initiatives, and kill some.
3) Start with your customer and work backwards. They need to be put at the centre of everything, without them, you don’t have a business.

Hope these help you out next time you’re feeling stuck.

P.S. Please excuse any typos. If I had to proof read and fix all grammar mistakes it would take me 3x as long to write – so you get it raw and real.

  • Taylor Barr

    Nice Post Dan. Some of the basics- but always good to return to them when in a rut.

  • Orion Blastar

    Sometimes I just take a break and start all over from scratch. If you don’t have a working business plan, then make one that works before doing anything else.

  • Pete James

    Hi Dan, great analogy of the weights and great advice. Thanks, Pete

  • http://twitter.com/Dimanya Dmitry

    Well done!

  • http://twitter.com/matthiasick Matthias Ick

    Spot on! My experience is that #2 doing less and prioritizing strictly, has the best effect. Focus on things that can make a difference (moving the needle and not just tiny improvements), that you are currently not do well and actually are capable of doing better if you invest more time & energy.

  • http://www.SEONick.net/ Nick Eubanks

    Thanks for sharing Dan, this post came at exactly the right time – I’m inundated with projects and “potential” to the point where it feels like everything is moving so slowly it’s frustrating.

    ‘Do less’ is sound advice, but I need to figure out how… my immediate reaction was to start chopping up companies and tech and selling them off, but that too requires time, effort, and focus if it is going to be worthwhile.

    How do approach lessening your project workload once it’s snowballed to something to large to be effectively managed?

  • Mark Perera

    Another great post Dan. If only large businesses took your advice – same rules apply.

  • Thom Lamb

    Great post Dan, as a new initiate into the start up game I’m knee deep in a lot of these questions and it’s great to hear some clear thoughts from someone that has accomplished many of the things I wish to accomplish – loved the gym metaphor too !

  • Kim

    Love it. Great reminder to refocus.

  • http://tathan.blogspot.gr/ Takis Athanassiou

    The why and passion clause, perhaps is the most important in your equation Dan, Excellent post in any case, but I’m thinking that the why, perhaps should be determined (in some elusive, general meaning, if not in strict terms!!!).

  • http://www.ottercreativestudio.com/ Emilio L.

    Hey Dan, you will think I am crazy but I saw your name on a meditation a few days ago and this is how I found you! I am too an entrepreneur (or business owner) and have been struggling with a few things recently. I am passionate about what I do but I found out there were more logs burning that I needed. So I got rid of them and focused on higher quality like you suggest. What’s happening at the moment is that I found myself working on a few projects that aren’t what I wanted or are not paying enough. I am responsible and clients are getting what they asked for. But, it is hard to focus when no time off has been taken. What recommendations do you have when it comes to relaxing and re-focusing? Do you go on vacation but still work? What about those companies like mine where there is still no “second hand” (someone I can trust as a project manager, I only have my developers) to take over when I need to simply go?

  • Yazin

    Just signed up. This is great!

  • Omar Asfour

    great post, Dan.
    type on point 2 “I probably reasses” –> reassess.

  • ideawebme

    Great Post Dan.

  • http://www.unpluggedrecreated.com/ Justin Harmon

    #2 is so true for me. I don’t know how many times I was stuck just trying to figure out which one of ten billion tasks I was thinking about. Definitely helps to just get rid of the clutter. For me it was shutting my brain off and just figuring out what was most important at the moment. Good stuff man. Glad I found your site just now.

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