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I’m sorry if I look like I know what I’m doing

January 9, 2023 by wroolie Leave a Comment

I had a conversation with a friend a few weeks ago who was starting her own business.  She was struggling with the people around her telling her it was just a hobby and how she was deluding herself. They caused her to doubt herself.  In my videos, she said, I always seem so confident.   Her question to me was… have I had these kind of doubts in the past? 

Hell yeah!  I’ve had those doubts.  And I still do.

There is a time when you are starting something new when you realise that you are the only one who believes in it.  It’s disconcerting. It causes self-doubt. It makes you wonder if you are just living a pipe dream or really doing something worthwhile.  You might blame others for “not getting it” and not supporting you—but ultimately, you realise there is no reason they should.  It’s your responsibility to take the risks and prove what’s possible.  It ain’t their dream.  It’s yours.

I’ve had successes and I’ve had failures.  And sometimes, it’s in between, and I have to spin it to be a “success” just to make myself feel better.  Momentum is the most important thing in life. When you have it, don’t let it go.  When you lose it, try to get it back.  I try to look at things in a positive light—I see no benefit to pessimism.

When you start something new, and no one around you has attempted it, you are going to get negative feedback. It could be from jealousy, but most of the time, it’s because your loved ones don’t want to see you fail.  They think you don’t see the risks. They think you don’t see how bad things can go.

But sometimes you see the risks, and you decide they are worth it.  

For every time I was patting myself on the back for being free from the 9-5, I had moments where I was tossing and turning at night worrying about bills and payroll and the embarrassment of failure. 

Self-doubt is always nipping at my heals. Sometimes, it catches me.  Sometimes, I slow down and lose momentum.  I become a tight-rope walker suddenly struck with vertigo.   

In my dark moments, I remember that there is another life I can live. I can be a highly-paid developer in London.  I can work at the biggest banks. I can solve all my money problems. I can be well taken care of. All I must do is give up my time and a bit of freedom. 

That’s tempting.  But…  it’s predictable.  It’s boring.

In my moments of self-doubt, I must remember why I started this in the first place.  I see evidence of avoiding risk all around me.  In the end, I might end up in the same place as the risk-avoider—but it won’t be for lack of trying.

Sometimes, this shit is hard.  And, if I make it look easy, then that’s amazing. 

I’m still a work in progress.

Filed Under: My Life, Overpass

Delegating and Giving up Control

January 12, 2016 by wroolie Leave a Comment

So, 2016 has started and we are already a week into it. It’s already going too fast.

I get easily frustrated with how slowly things change. It usually takes other people to remind me how far I’ve come.

At the beginning of 2015, I had a small team and no work. I was so worried and struggling to keep my head above water.

At the beginning of 2016, I have too much work. Too many clients. The problem is that I have not been very good at delegating. I am up in the crazy hours of the morning and late at night doing work for clients.

The problem is with me. I don’t feel comfortable giving up control. I can do it faster and better, so “just let me do it”. This is my big mistake.

I have a teenager who is learning to drive. As I sit in the passenger seat with no control, I feel terrified. I want to just pull over and take over the wheel. But, if I do that, he doesn’t get better. So, I have to get used to having no control.

The same is true for delegating. I need to get used to giving up control. I’ve been bad about that this past year. Overpass won’t grow if I can’t relinquish control.

That is what I’m going to try to do better this year.

Filed Under: Overpass

Talent alone is not enough

January 3, 2016 by wroolie Leave a Comment

If there is one thing I always want my kids to know, it’s that talent alone is not enough to do well in this world. Even the most talented people in the world can’t make it unless they put in the hard work necessary to make that talent count.

I recently had to let go of a member of my team. It’s a difficult thing to do as it increases my workload, but it was necessary. This seems to be a routine thing and I guess I should start getting used it.

I have a team member who started so strong and quickly became indispensable. She was talented and I felt so lucky to have her on board.  I mean, I could not believe my luck!  But, in recent months work started to get very slow and, being an online worker, I rarely saw her online in order to chat on Slack. Tasks that should have taken hours were taking over a week. But, I loved her work (the work she did) … so I let it continue but expressed my concerns. This is always a mistake. I’ve made this mistake before.

A few days ago, I found she had several online profiles for looking for full-time work with different names.  Who knows how many “full-time” jobs she has besides working for me.  I’ve been here before too.

I have to say, her talent tempted me to overlook this too.  I mean, she did great work when it was done.  But, in the end, I had to let her go. This is a problem with online workers paid based on time rather than projects— you never know how much time you are actually paying for. I need to start re-thinking my strategy here. When you pay a full-time person based on time, you can train them and help them grow— but you are also paying for a lot of what you don’t need and putting a lot of trust into the process.

A few years ago, I had hired a super-talented designer. I felt so lucky to have him working for me. I loved his work and our clients loved his work.  He worked for me for over a year. But, he was incredibly unreliable. He would go missing for days or weeks and cause me a lot of stress with clients. His talented kept him on longer than it should have, but in the end I could not continue. Same situation as now.  Talk about not learning from your mistakes.

I myself know better than to fall into this trap when I work for others. My talents (or previous hard work learning new things) are what get me jobs and contracts. My hard work is what keeps them.

Talent will give you an edge and it may even help the small stuff go un-noticed. But in the end, it is not enough.

Now, that 2016 has started, I intend to re-evaluate how I’ve been working. This is healthy and reinvention comes every couple of years anyway. With Overpass, we’re going to reduce the amount of client work we do and put more effort into our own products. Every day, I learn more and more.

Filed Under: Overpass

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