5 Ways To Protect Your Confidence As An Entrepreneur

5 Ways To Protect Your Confidence As An Entrepreneur

Over the years I’ve had some pinch-me-is-this-really-happening kinds of moments.

From spending a week with Richard Branson, to having Mitch Kapor (inventor of Lotus Notes / spreadsheet) invest in my company, Flowtown.

One of those moments happened in 2009 when somehow we got introduced to Gail, the CEO of ConstantContact – the FIRST publicly traded SaaS (Software as a Service) company in the world.

We met at our offices and she started asking questions about the product, how we came up with it, where we were at, etc..

… then she smiled and she said something I’ll never forget.

Don’t forget to document the journey… someday you’ll reach your destination and wish you could travel back and appreciate the early days.

So we did.

We captured everything from screenshots, to team photos.

However, this was the cool part.

The unintended side effect was that it allowed us to remind ourselves of the progress we were making.

Seeing how we evolved the product, the team, even our environment…

… and that led me on this discovery that one of the most important challenges an entrepreneur faces is protecting their confidence.

It’s one of the most important (yet underappreciated) assets you own as an entrepreneur.

And with a constant barrage of “doubt bullets” being fired at your most precious asset…

… it’s time you protected it with a thick layer of emotional kevlar.

That’s why I wanted to share a few ways you can do this in this weeks video.

During the video I break this down into 5 strategies… the last, one I use everytime I go to write emails to you… for me it’s super important to ground my mind and express the journey.

1) Celebrate The Wins (Previous Quarter)

2) Weekly Team / Customers Wins

3) Document The Journey (Screenshots / Recordings / Photographers)

4) Yearly Party (Review Wins/Losses)

5) Achievement List

Maybe you’ve had moments of pure confidence in business?

What happened in your life just prior? Was it intentional?

Regardless, I would love to hear from you in the comments… let me know how you build your confidence to take on more challenges in life?




  • http://www.nichesocialnetworks.com/ Chris Spurvey

    Thanks for this Dan. I think you nailed it. I do find that utilizing a daily routine helps. Each night celebrate a few small wins and taking a moment to reflect on a thing or two I could have done better. I find in the reflecting on the things I could have done better it is important not to beat myself up about the particular thing. Instead focus forward and imagine building upon the learnings.

    • http://twitter.com/danmartell Dan Martell

      Chris, do you use the 5 Minute Journal?

      I’ve been using it for 3 years now.

      One of the best journals to start / end a day.

      Appreciate the comment.


      • http://www.nichesocialnetworks.com/ Chris Spurvey

        Your welcome Dan. I am on my 4th copy of the 5 Minute Journal. 🙂 it has had a great influence.

        • http://SteveDaar.com Steve Daar

          my 3rd copy came in the mail a couple days ago!

          Dan / Chris – do you use anything daily similar to the 5MJ but more from a work/productivity standpoint (i.e. ‘The Passion Planner’, ‘The Freedom Journal’, even something as simple as a blank piece of paper that you draw some lines on)?

  • http://SteveDaar.com Steve Daar

    Hey Dan,

    A couple months a SaaS startup hired me to do demand generation, conversion optimization, etc.

    Among the owners / managers of the company, I feel there hasn’t been much celebration for the growth…..the general sentiment is that we’re not growing fast enough.

    The good is that in the last 3 months, MoM revenue growth has been 46%, 70%, 44%

    The bad is that the absolute revenue totals aren’t all that impressive and ROAS is not yet break even.

    (Although the positive part of that is ROAS has gone up almost 100% over the past 3 months)

    Day-to-day I feel kind of down about the whole situation because the perspective as a whole of the team is one of “not enough”.

    As employee as opposed to entrepreneur/business owner, does anything from the above video / text change?

    – Steve

    Did the first “premium interview” as discussed a little while back. The page looked like this: http://profithacking.com/nicholas-kusmich-facebook-ads-interview

    Reasonably good conversion rate (over 50% of everyone who landed on page took one of the packages but almost all took the free one & almost all traffic was very warm)

    Hypothesis After First Test:
    Feel the page was too much. I was a bit married to “my” idea of having a mock-crowdfunding page for a “pay what you want” offer. No one else cares. They want what they came for.

    As a result, the next test is going to be a much shorter, much simpler page. There will be two offers: One that is Free and one that is Premium.

    Will see how it affects overall conversion rate, total revenue generated, etc.
    Possible that we live in a world now where selling a type of content where there is an arguable over-saturation already (podcasts / interviews) is a “no go”

    • http://twitter.com/danmartell Dan Martell


      Here’s something worth considering … the founders sentiment of “Not enough growth” is more likely their own insecurities and frustration with their own performance projected on the team.

      So know it’s not you, it’s them.

      You could suggest that employee morale would increase if you celebrated the small wins.

      It’s how were built as humans to grow.

      It’ll only help his company in the long run.


      • http://SteveDaar.com Steve Daar

        Appreciate the perspective, Dan.

        In the past week since leaving my comment, we had our highest revenue week to date and yesterday was our highest revenue day ever – – feels as good of a place to start celebrating as any!!

        Brainstorming now about how to bring more of a culture of celebration here as well as how to keep my internal state/feelings positive even if the team/leadership doesn’t adopt it as well.

  • Wes Jones

    My partner Nick and I document our progress in weekly logs which has been invaluable. We each write one from our own perspective (Biz Dev & Tech). Shows how far we’ve gotten as well as acts as a reference for why we made decisions we did. medium.com/vrbtm

    • http://twitter.com/danmartell Dan Martell

      Wes, love that / great way to reflect and adjust going forward.


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