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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

New Years Reclamations

January 2, 2023 by wroolie Leave a Comment

I did a video for Overpass Apps a few days ago about New Years Resolutions. This is my favourite time of year, and I put a lot of effort into coming up with resolutions for the next year. It’s the 2nd of January, and I’m pleased to say I’m still going strong (that is supposed to be a joke). The coming days, weeks, and months may see some resolutions become victims of my laziness or overindulgence. But for now, I’m carrying them all with me.

A few weeks ago, I was in my storage unit looking for my artificial Christmas tree when I found a notebook which held my resolutions from 2003. 20 years ago. That was humbling. Some things I did, many I didn’t, and others I accomplished for a while and never kept up with.

At the age of 50, I find that my resolutions are no longer unique. They turn up again and again. And many of them are geared towards starting something I used to do or being the way I used to be. In effect, they are not resolutions but reclamations of my former self.

2022 was a year of ups and downs for me. I did many things I’m proud of (like travelling more, spending more time with family, etc.), and many I’m not. Just like anyone else, there are times when I take my eye off the ball and need to refocus.

And sometimes, I have to acknowledge that I’m not the person I used to be. I’ve gained new skills and behaviours that I love, but I also lost some that I used to be proud of. So I must reclaim them. I need to realise when I’m off course with who I want to be.

Most people I have spoken to talk about how ridiculous resolutions are. “You’re going to end up breaking them anyway, so what’s the point?” and “It’s just a day. Why not choose a day next month instead?” It sounds so defeatist to me.

The most significant accomplishments of my life came when I decided to do something out of the ordinary. They came when I decided I didn’t want to be in a boat without oars floating in whichever direction the current pushed me. Despondency came when I took what I was given without questioning it. I have to remind myself sometimes that I don’t have a normal job because I decided I wanted something more and took those risks. I have to remind myself that I have friends all over the world because I decided to do videos every day (another New Years resolution). I have to remind myself that I’m holding the oars of this boat.

In “Man’s Search for Meaning”, Viktor Frankl spoke of our need for meaning. While Freud argued that we seek pleasure, Frankl spoke about meaning– which was much different. If there’s one thing we all have now is easy access to pleasure and dopamine (and how many unhappy people are there?). If there is no meaning in your life– even if it’s one you create for yourself– you will never be happy.

I want my life to have meaning. I want to live out the narrative I see for myself. That narrative includes losses as well as wins. It includes falling down and getting back up. It includes doing stupid shit and feeling totally embarrassed, but also things doing I’m really proud of. It involves finding the best people to surround myself with, as well as making mistakes and sometimes choosing wrong. If my life is a day at Disneyland, I want to leave saying I’ve been on all the rides.

So, I believe in resolutions. I believe in goals. I believe in refocusing. I believe in taking back control.

How’s that for a ramble?

Filed Under: My Life

Is Age really just a number?

July 22, 2022 by wroolie Leave a Comment

“Age is just a number.” 

I hear that all the time. It usually is said by someone who is surprised to find out how old I am.  I’ll meet someone new, and we’ll be talking about something in pop culture, and I’ll mention a show or song from my youth that they never heard of.  This is when the age discrepancy comes out.  Sometimes, it’s in the decades!

And then, they’ll say, “well… age is just a number.”  It’s become so cliche that I hear it so often.  

But it isn’t just a number, is it?

I totally get what they are saying.  Just because you are a certain age doesn’t mean you should feel that age or act that age.  We all know people in their eighties who act like teenagers and people in their twenties who act like life is over.  I still feel like I’m figuring things out.  I feel like I haven’t become an adult just yet.

I guess the “age is just a number” phrase bothers me because it doesn’t need to be said.  It’s like the other person is trying to say something to console me when I don’t need consoling.  

I was watching some stupid movie on Netflix a few weeks ago.  It was called “The Secret: Dare to Dream” (I had to look it up because it was so mediocre).   A man was at a birthday party for a female friend of his. And she had a teenage daughter. The daughter was talking about s’mores and the man mentioned how he loved those. 

“How do you know about s’mores?”, the young girl asked.

“You don’t get to my age without having lived a little,” he said.  

I loved that.  You don’t get to my age without having lived a little.

To say age is just a number like saying the time on the clock is just a number.  It’s like saying the odometer on your car just displays a number.  It’s like saying the number on the scale is just a number.

I’m the first to admit that I freak out on milestone birthdays.  Next week I turn 50.  

When I turned thirty, I asked what I was doing with my life.  Everyone I spoke to who was over thirty talked about how I had nothing to worry about.  I wondered if I was on the right track.  Am I living my life to its fullest, etc.  Shortly afterwards, I started Overpass.  I stopped being a permanent employee.  I looked at people in the same job I was in at the time who had been there for twenty years and it scared me.  

When I turned forty, I freaked out again.  Overpass existed, but I really just did contracting with it. After years, I hadn’t really found any clients.   It wasn’t moving as fast as I hoped. Maybe I wasn’t taking it seriously enough.  And … forty?  That seemed like such a huge number.  That same year, I created my first app.  Later, I started the YouTube channel.  

That “just a number” is what forced me to push myself out of homeostasis.  It allowed me to evaluate where I was settling and to remember all the goals and dreams I had but stopped trying for.  I never feel like I’m over the hill or that life is over.  I’m just getting started. But it’s a nice time-check to let me know that I might be spending too much time on the things I’m not that interested in.

It’s funny how we always assume everyone else is the finish product but we are still a work in progress.  

I definitely feel like a work in progress. I wish I could wear a sign that says “under construction.  Please excuse my mess.”

I’m not done.  I plan on living a little.

And I look forward to my fifties.

Filed Under: Growing Up, My Life

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