Lessons from a diligent failure

Diligent — being careful and hard-working

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Image by Sasha Freemind on Unsplash

In February 1998, the world kept spinning.

An obvious statement now, but at the time, I felt like it was the end of the world. I was 19, socially anxious, and had just dropped out of university because my sporadic part-time clerking jobs weren’t enough to pay the way. I was lost. I had always been a diligent student. Now I wasn’t.

Hard work = success

That’s what I knew from school. Shut up. Head down. Do the work.

But what if that’s all you know?

I didn’t know what I didn’t know, so I secured a scarily high-interest loan to get into a technical college.

The college got me my first job. I didn’t even need an interview. It was an eLearning production house that needed HTML developers for a looming deadline. It was the first time my insomnia worked in my favour, as we pulled all-nighters to make the deadline. It wouldn’t be the last. Within six months of joining, I was promoted to team lead, responsible for the quality of everything my team did. The diligent student became the diligent worker. My team never missed a deadline, despite tougher conditions and shrinking deadlines. The company changed its name four times, and we moved offices practically every time it did.

I made it to 2007 before working nights, weekends and holidays finally burned me out.

My next job was better.

It wasn’t in eLearning. It barely had anything to do with my training at all.

I was now a copy editor and designer in a creative team. It’s where I met my first mentor, Tessa Skerbinek, a talented product designer willing to help the curious new designer develop taste and appreciation for corporate brand identity. The first three years of that job were the happiest period of my life. It was an innovation-hungry environment that encouraged learning, creativity, and ideas. It was a safe space to celebrate failures and share wins with other teams. We grew into user experience — a maverick team putting our customers first.

Companies change.

Not always for the better.

Diligence got me through it.

In 2015, my family and I decided to move back to Scotland. I came over first.

It was another career shift. This time into editorial design and content management in a communications team. It’s where I experienced the first soul-crushing humiliation of my entire career. I guess I was lucky to have made it this far unscathed. But, still, diligence got me through it.

Until it couldn’t.

It’s February 2018 and I find myself in almost the same conditions as I was in 20 years ago. Some things are different. This time it was my choice. I’m anxious, but I have a plan.

More importantly, I finally have some advice to share with my younger self. The older me needs to pay attention to this too.

1. Diligence is not enough

By itself. Keeping our head downs and working hard does not make us successful. Maybe it did once upon a time and that’s why our teachers and parents kept encouraging us to do it, but nowadays ‘head down’ means invisible.

If you want to grow, you need to be heard.

2. Don’t be too stubborn to let go

Sometimes we attach ourselves to an idea. It’s something we don’t think we can budge on. I went to technical college and learned programming. From that day, I thought of myself as a ‘woman in tech’. Even when my career was shifting away from tech, I still held that label in my head. I’ve only recently let it go. I myopically refused to read the signs that my passions are not in technology, but in helping people be understood in a noisy, technological world.

Letting go can be a powerful and terrifying thing, but it’s what you have to do if you want to move forward.

3. Find your tribe

I’ve been going to tech meet-ups on and off for the past few years. Social anxiety makes it difficult for me to engage with others. Some days are better than others, but I usually make small talk and no lasting connections. That’s not an option if you want to be successful at freelancing, so because I had the time, I decided to go to a Creative Mornings event last month.

It was like being hit on the head with a road sign from the universe.

I’m a creative.

This is my tribe.

A tribe is connections. A tribe is a network. It’s no surprise that all of past freelancing came from people I already knew.

Find your people. They’re out there.

4. Sell your successes

As diligent workers, we don’t usually pause long enough to sell ourselves. We just get on with it. That was okay in school. Teachers liked us because we didn’t bother them, and our report cards always praised our diligence. In business, we’re all grownups. No one really notices the quiet ones who keep to themselves. Sure, they miss us after we leave because the dam we’ve been quietly shoring will suddenly start to leak from a dozen places, but they won’t value us while we’re there.


Because they have no idea what we actually do. Just that we deliver. They don’t know that we had to call in favours and MacGyver a system to make it work. And yes, we think improving bad processes is simply part of our jobs, but we still need to quantify those successes and share them.

Write them down. Toot your horn.

5. Don’t give your worth away for free

When we’re naturally diligent, we don’t just look at the ‘one task’ we’ve been given. We look at the big picture. We see the loose bolts and missing screws of a process. We see the compound interest that stacks up once a terrible process is ignored. It’s in our DNA to want to fix it. We’d rather invest a lot of time in the beginning to make sure the work we do is still running smoothly a year, two years, ten years down the line. We can’t abide the glut of inefficiency, and bosses are usually happy with us for sorting it out.

But there’s the problem.

Fixing these problems is often not our jobs, but we go ahead and do it, and run ourselves ragged trying to keep up with the work we have been assigned.

It’s dangerous because it becomes expected.

Looming deadline but everything is a mess? No problem, chuck the diligent worker on it.

It might feel good to believe we are valued, but when that coworker who only delivered exactly what had been asked gets a promotion because they used their free work time to up-skill, those good feelings aren’t enough to stop the massive blow to your self-confidence, or possibly your career prospects.

Pace yourself. I know you often ask yourself “If not me, then who?” but sometimes you need to choose your battles carefully.

6. Mind your mentor

A typical ‘head down’ introvert, I never knew the value of having mentors in my career. I’ve since been to some events that talk about the importance of mentors. Most mentors give great guidance, but many often sponsor someone for a promotion or better job. Unsurprisingly, there is some anecdotal evidence that a lack of mentors is why we don’t see a lot of progression of diverse candidates in certain fields like technology.

I’m grateful for my mentor. She taught me a lot about design, fought on my behalf, and taught me to fight for the user and my team. I’d like to think that I will do the same for someone else. I know I still have a lot to learn, so I will never stop paying attention to people who could be a potential mentor. They are everywhere, if we have the courage to reach out to them.

Be brave. Listen to your mentors. And if you can’t find one, be one.

7. Have a passion project

I usually throw myself entirely into my job. My free time is spent on research and skills that are directly related to it. I used to think that was a good thing, but we’re heading into a future where no job is secure, so devoting all of my free time to a job that might not exist in a few years suddenly seems short-sighted. Automation and AI are just a couple of reasons why our jobs are going to change. We are all going to have to learn to pivot. No one — not employers, employees, or recruiters — is prepared for this reality yet.

The safest bet is to fill your free time with the things that make you curious — that make you lose time. Have a passion project, a side-hustle, or whatever you want to call it. If you can figure out how to make money from it, that’s even better.

Don’t be your job. It won’t always be there. Be you.

8. Look after yourself

Burn out is one of those things that some people either believe in or they don’t. My GP did, an endocrinologist didn’t. I believe in it. I burned out once ten years ago, and came close to burning out again last year. The first time I burned out was because I could count the numbers of days I hadn’t worked in the year on my fingers. It took me years to physically recover.

Last year was a surprise. I was putting in 40-odd hours a week. Hardly back-breaking. That’s when I realised that the work I do has to be meaningful to me too. Diligence isn’t about pride or pay, it’s about worth. If I don’t feel I’m helping people, then I don’t see my worth. If I don’t feel I’m learning how to help people, then I don’t see a job’s worth.

We all have to follow our core values. Sometimes, we’re lucky and we can shape our work. When that’s not an option, we have to walk away. Listen to your body.

Thank you for reading!

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