How Past Successes Can Hurt Your Blogging or Freelancing Career
  • Save

How Past Successes Can Hurt Your Blogging or Freelancing Career

We may earn money or products from the companies mentioned in this post.

One of the strangest truths about self-employment is that people who have been successful in school and jobs often have a difficult transitionto a more entrepreneurial lifestyle. Many give up before they ever get any traction. Meanwhile, I’ve seen plenty of dropouts, job hoppers, and former C-students building huge blogs, racking up clients, and enjoying incredible success at self-employment. But why?

Too Much Success Makes Failure Scary

When your life has been filled with win after win, failure remains an unfamiliar and scary thing. It’s easy to start thinking people like you because you’re smart and successful – and that they wouldn’t like you if you weren’t. You get used to hearing “yes” and “good job”, and you may subconsciously structure your decisions to keep those wonderful words coming your way.

Unfortunately, the only way to maintain the string of successes is to avoid situations where you might fail. You hang out in your comfort zone, and we all know nothing great happens there. In fact, staying in your comfort zone is basically failure by default. [su_highlight background=”#faff6e”]As JK Rowling once said, “It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all – in which case, you fail by default.”[/su_highlight]

If you haven’t watched her Harvard commencement speech on failure, it’s absolutely worth the 20 minutes it takes to watch it.

A blog that never really takes off sucks, but it teaches you things you need to know to either correct course or make the next one better.

If you’ve been mostly successful in life, you don’t really know that. You may understand it intellectually, but there’s a more primitive part of your brain that hasn’t bought in. It’s the sneaky, cowardly part, and it will do everything in its power to stop you from taking the risks that might lead to failure or embarrassment.

Think Back to Your School Days…

Back to school
  • Save

It’s hard to overcome the desire to avoid failure. After all, most of us spent 12 or more of our most impressionable years being punished for every small misstep. Depending on where you went to school, an A grade probably required you to perform your work with no more than a 7-10% failure rate. Where I went to school, anything under a 95% was an A-. That's not a lot of room for error, especially not when the adults in your life are telling you YOUR ENTIRE FUTURE RIDES ON IT.

I understand why it works that way. Creating an effort or improvement-based grading system would be terribly complex, especially in large classes. Effort is great, but it says nothing about whether someone’s ready to move to the next level. Improvement might  be better, but everyone starts at different levels and teachers can’t reasonably teach at enough different levels to ensure everyone gets to improve at the rate best suited to them. So, (most) schools end up providing a one-size-fits all experience that greatly penalizes experimentation and failure.

After 12 or more years of that, we start to feel like that’s how all of life will be. We feel like we need to have a high success rate, and only attempt those things where we know enough that we’ll get things right the first time. We take the actions where we know we can get an “A”, because on some level we're still afraid of a “C” bringing down our average.

The problem is that life’s not like that. There's no overall life GPA to worry about keeping up. To be successful, you have to be willing and able to face tons of failures and mistakes and know that they don't make YOU a failure – and in fact, it’s the only way to be a success.

Probability is On Your Side

Whatever you want to do, action is required to get you there. No amount of research and planning can stave off failure, and if you waste too much time on those things, the opportunities you've been thinking about will often pass you by before you get to them.

Nothing offers better instruction than action and experience. Do a bit of preliminary research, sure. Talk with a couple people who've done what you want to do. Then get started.

You might create a blog and spend six months on it, only to find you've been writing for a market that doesn't exist. That's not idea, but it's okay. While you were doing that, you were learning all kinds of important blogging skills – working with WordPress, how to make affiliate links, how to research keywords, and so on. You were building habits – blogging regularly, setting boundaries in your life to make room for something new.

You're succeeding – you just don't know it yet.

The same goes for pitching clients. Every “no” gets you a little closer to a “yes”. That's true both mathematically (ask enough, someone will say yes) and progressively. Each time you pitch, you're making adjustments and learning a little more about what works and what doesn't. As you accumulate more and more “no” replies, you'll start to see patterns – which types of companies respond to different subject lines or pitch styles, which services generate the most interest, and so on.

You're also making contacts with people who may not need you now, but they might in the future. They might know someone else who needs your services. Every step you take is getting you closer to your goal, even if it seems like some are moving you away from it.


“No” Isn't Failure; It’s Research

To get over your fear of failure, you need to reframe your thinking. Tell yourself (often) you’re on a research mission.

How Past Successes Can Hurt Your Blogging or Freelancing Career
  • Save


If you're blogging, learn to pay attention to your stats, then use a combination of Google and online tutorials to help you figure out how to improve them. Pay attention to:

  • Post interaction
  • Post shares
  • Total traffic
  • Traffic by source
  • Time on site
  • Search engine rankings for relevant keywords (with at least some amount of traffic)
  • Bounce rate
  • Reader comments/feedback
  • Site speed
  • Social media stats (like number of repins, comments, like, etc)

And so on – they're not all going to be equally important to all bloggers, but those are some good metrics to start looking at as you learn the ropes. You'll likely fail spectacularly on many of them, but you'll also learn as you go. Your first site may not be a winner, but you'll learn things to apply to your second or third site – and if you're trying and learning consistently, it's virtually impossible NOT to make money eventually.


If you're trying to get freelance clients, study the replies you get. For best results, create a spreadsheet to help you better pull out the patterns. Give one line to each company you pitch, and track the data you want to study. I recommend the following columns:

  • Company name
  • Company size (either in reported revenue or number of employees – you may have to guess for smaller companies)
  • Person pitched
  • Title of person pitched
  • Type of project you pitched
  • Industry
  • Day of week of initial contact
  • Month of initial contact
  • Time of day you initially made contact
  • Means of initial contact (email, phone, in person, LinkedIn, etc.)
  • Stated objection or reason for declining

You an add other fields if there are other things you want to track, but that’s a good basic list to get you started.

Once I have clients filled in, I like to color code the rows – green for the ones that become clients, yellow for the ones that respond in some way, and red for those that are completely silent. As time goes on and you have 50, 100, or even 500 pitches logged in your spreadsheet, you can sort the rows by color and look at which factors seem to give you the best (or worst) results. If you don’t like a colorful spreadsheet, you can do something similar by creating an extra column for YES/NO/PROPOSAL, then selecting that column and sorting A to Z.

When you study your pitches like this, you turn it into a data-gathering project instead of this big, emotional thing where your feelings get a little hurt every time someone says no. You may also uncover problems you didn’t know you had. If you’re consistently getting to the proposal phase with GIS companies but not signing any of them, that could be a sign that you need to get feedback from someone in the industry to figure out what you’re doing to turn them off. It could also be a sign that maybe you don't REALLY want to work with that particularly industry and your lack of enthusiasm is coming through in your pitches.

Every Successful Entrepreneur Has “Failed” Many, Many Times

If all else fails, remind yourself that every successful blogger or freelancer or speaker or writer or entrepreneur has “failed”. I put failure in quotes to remind you one final time that short-term failures and mistakes and rejections aren't REAL failure. After all, who would you rather be? The guy who gets rejected 95% of the time but earns $5k, $10k, or even $50k/month doing what he loves – or the one who earns nothing because he never really tried.

Share via
Copy link
Powered by Social Snap