Measuring Success – When You Feel Like a Failure

Ever get into one of those ruts where you start to question if you’ve actually -done- anything at all?

Lately, I’ve been feeling like a failure. I log in here to check on things, adjust profile images, put up new workshop dates, and I wince – the date of my last blog post gets further and further away from today’s date with every day that I don’t write. I’m a cliche – a writer who doesn’t write, a blogger who doesn’t blog.

November has this effect on me, I’ve noticed – the days get shorter, the nights get longer. There’s a strange moment of limbo that business owners who work with other business owners find themselves in – many creatives are feeling the crush of Christmas orders and have put personal development on hold, leaving me eager for the period AFTER Christmas, when reflection and planning for next year starts. But more than that, I start to take stock of what I’ve been up to, and how well I’ve done.

My busiest time of year has always been the first four to five months. From January to May of this year, I visited 9 cities, met dozens and dozens of amazing, inspiring people, taught and spoke at conferences, small engagements and held workshops, and then, hit a natural slowdown period over the summer. With my kids out of school, I didn’t travel, except with them, I worked less, and wrote less, though we did also completely redo the Vivid & Brave website, and wrote Social Media Infusion in that time. When I sit down and measure things like this, I feel that this year has been a great one. My word for the year was resonance, and everything I did matched it – I worked towards my ultimate goal, my passion – to continue to work with creative women in transition, to teach, speak and write. I did those things.

So, let’s talk about the long silence here on the blog. I was beating myself up over it something fierce, when I realized what I  have been doing in the interim. My calendar for October, November, and December is littered with speaking engagements, volunteer work, and Christmas events. I’ve been working on handmade Christmas gifts, and also dealing with Murmel being sick twice in less than a month. I haven’t been idle. And yet, without the tangible, public, forward facing proof of my efforts, I feel I’ve fallen down on the job.

I think this happens when we start to measure success by what we do – tasks we complete, posts we write – instead of the less tangible things that are moving us towards our passion, every day. Last week I delivered a really fun talk about Self Care & Self Advocacy to a small group of moms, and I didn’t talk about it much because it was a private event. I haven’t decided yet if I’ll add it to my offerings. But that spoke to my success far more than another checkmark on my to-do list does. What I do to keep Vivid & Brave running is important, but who I am when I show up every day to do the work is vital. Success isn’t measured by how many things I manage to get done – though they definitely contribute to it.  Success is about living out my why, my passion and purpose, all the time.

How have you been measuring your success?


Stephanie Ostermann

I’m the sort of girl who you meet for coffee and end up pouring your entire heart out to. The friend you come to when you need someone to call it straight. No bullshit. No extras. Just truth.

I’m a communicator. That’s a PC way of saying I like to talk, but I also spend a lot of my time listening, and over the years, I’ve developed a sense for subtext – how one or two words can change your entire message, what people are really trying to say and how to weave the varied layers of your story into one cohesive brand message that your clients fall in love with.

When I'm not acting as editor in chief for Vivid & Brave, you can find me geeking out over words here.

Latest posts by Stephanie Ostermann (see all)