Success Advice
The 17 Greatest Lessons I Learned In 2018 That Will Change Your Perspective.
It’s that time of year again. It’s time for me to share what I learned this year — not for my benefit but for yours. You’re going to see a little bit of yourself in each lesson I share.
Every lesson will have actionable advice that will get you on the way to being the person you’ve always dreamt of being in 2019. It’s been a tough year for me where I’ve tried to push the boundaries even further and what has come with that is even bigger failures.
You’re about to see why I didn’t give up in 2018 and how this year will go on to define the rest of my life — and yours.
Here are the greatest lessons I learned in 2018:
We all have leadership inside of us.
The greatest lesson I learned in 2018 was about leadership.
I realized that I wasn’t looking to work in Digital Marketing. I realized I was looking for something and that something was leadership. I’ve worked in so many industries with so many types of products in my career and that never motivated me. This year I learned that motivating others by being a role model was the biggest piece of the jigsaw puzzle that I was missing.
Every one of us can be a leader and for some of us, this is the thing we’ve been ignoring without knowing why.
Maybe you don’t want to build influence online; maybe you want to be a leader instead.
Never let bullies ruin your passion.
My social media following exploded in 2018.
Who gives a crap about numbers of followers, though. What I learned is that as the audience for what I do got bigger, I became a target not just for trolls, but for groups of trolls whose sole purpose is to get together and take down people who have a loud voice online, by spamming their posts with comments of hate to scare others away from engaging with what you do.
It nearly made me give up blogging and I embarrassed to say that — although it’s true. A bully here and a bully there is nothing unusual. In 2018 I had hundreds target me in the space of a few weeks.
I defeated them by ignoring, blocking and deleting their hatred. They ended up moving onto bully other people because I was no longer ‘fun’ in their eyes.
The hardest part about dealing with the bullies was finding a way to forgive them.
Hating bullies is level one.
Defeating bullies is level two.
Forgiving bullies is the level that all of us should aspire to reach.
Massive change takes longer than you think.
Career change was my focus this year. I told everyone it would happen in a couple of months because you know, I have a few followers on Linkedin so this should be a piece of cake, right?
Wrong. It took from January of 2018 until October 2018 to finally begin my new career. It involved 50+ interviews and more rejections than I faced in 2017 when I took on the dating world and got told I was ridiculous, ugly, annoying or ‘nothing special.’
The point is this: whatever massive change you seek in 2019, understand that it will take longer than you think.
Don’t make the mistake I did of bragging what your new life will look like before it’s even close to happening.
Calm down.
Take a chill pill.
Enjoy the journey.
And have unwavering patience.
Momentum takes years to build and months to witness.
I’ve been building a side-hustle for a few years. You’ve heard me say that many times before and I know you’re sick of it.
Whether you give a crap about my side-hustle or not, what I learned in 2018 is that for years it will look like nothing is happening. Then, out of nowhere — assuming you’ve put in the work — you will gain a lot of momentum quickly.
This year I made more money from my side-hustle than I could have ever expected. It didn’t happen by accident or by wishing or some wiz bang goal list: it happened because I’d focused fours years of my life on it and had earned the right to deliver value to a small group of people who were happy to pay for my time.
Momentum will happen when you’ve earned the right and found a way to create value for one person (not millions of people).
Opportunity comes from the place you least expect it.
I had a coffee with this guy. He was nice. It went nowhere.
I spoke with another gentleman who ran a call center. That chat too felt like a waste of time. Then, I met an old colleague and had another chat that seemed to go nowhere.
That chat then led to a phone conversation with someone in recruitment. Nothing special happened during that conversation either. On the next call, they gave me an offer — it was laughable.
Three more phone calls happened and before I knew it, I found myself saying yes to an opportunity that I couldn’t find advertised anywhere else.
Quit focusing on what you’re getting from every conversation. You’ll never know where your next opportunity is coming from, so be a nice human being to everyone you meet.
Watch the magic happen from there.
Meditation is *not* bullshit.
I tried in 2017 to meditate and in 2018 I almost gave it up.
Meditation is a slippery art to master and it makes no sense when you read about it. What you think is failure in meditation is in fact success.
The practice feels like it’s going nowhere until it takes you to this mystical place deep within your sub-conscious where you’d never expect to end up.
Searching through your sub-conscious helps reveal treasures that were previously hidden — treasures like patience and stress relief. Taking a step back from the three-dimensional world we all live in to see what lies in the darkness and what our thoughts are really saying about us is a practice everyone should start in 2019.
If you’re not meditating, then you’re not living.
The market is the market.
The end of 2018 has been a challenge for the financial markets. Property has been effected, Cryptocurrency didn’t reach $1M a coin and the stock market took a huge hit.
The market is the market and you’ll never predict any of this. Don’t let the markets suck up all your spare time and stop you from doing stuff you love. Diversify, invest in yourself and stay away from high-risk investments.
Your earning capacity has more to do with the person you are than the market. The market is the market young Gecko.
Value time over money and you’ll make more money(weird, huh?)
This year has been all about valuing my time better.
Less coffee catch ups; less random Skype calls; less doing work I hate. Instead, I’ve focused on time instead of focusing on money.
This philosophy led me to doing a four day work week (not a 4 hour workweek for the Tim Ferriss fans that are reading).
Doing four days a week has allowed me to use the fifth day to work on side projects and find out what my career might look like in a few years. Maybe you don’t need to quit your job in 2019.
Maybe you could value time and do a four-day workweek so you can explore the depths of your hobbies and see if there’s any treasure buried inside one of them that you’ve never had time to search for.
20% less income can lead to more income than you’d ever expect if you give this experiment a go. That’s what it did for me.
Transformation brings unexpected surprises.
I thought I wanted to work in digital marketing, but I actually wanted to be a leader.
The transformation I went through this year took me down many paths that all felt like they led nowhere. I began my career in digital marketing and realized it was leadership I always wanted to do.
Transformation doesn’t always bring the result you expect and that’s the whole reason you should embrace the idea of transforming.
Through change, we discover what we care about and what is completely useless.
Transform in 2019.
Who you become next year is based on the previous year’s results.
I’ve laid the foundation in 2018 for the following year. Next year is going to be exciting.
What I’ve learned at the end of every year when I write this same article — where I summarise the year — is that what you do the year before lays the foundation.
If you want to see a different future, then you need to start making changes in 2019. Just getting on with starting something is the most important step.
Quit goal setting, thinking, dreaming, envisioning and take one small action. Then another. And so on.
Every year you are building on the previous years results. Start now.
If you want to increase your productivity and learn some more valuable life hacks, then join my private mailing list on timdenning.net
Success Advice
Signs You’re Ready for a More Purposeful Career
Doing well at something is not the same as wanting it. Plenty of people are steady at their jobs and still feel hollow at the end of the day. Nothing looks wrong from the outside. Colleagues respect you, the pay lands on time, and you handle whatever gets thrown your way. What builds underneath is harder to name.
A dullness sets in, or a restlessness, or the sense that you’re watching your own work from across the room. It doesn’t mean everything needs to be torn down. Often it just means you’ve stopped growing, and once that happens, what counts as worthwhile work quietly changes shape.
When work shifts
There is usually no announcement. One day the tasks that once demanded your full attention take almost nothing out of you. Some people notice their focus sliding away from the work and toward the people around it. Wanting to mentor, listen, and help someone untangle a problem tells you something real about where your attention wants to go.
This lands hard in teaching. Class sizes and schedules leave little room for one student who needs an hour, and administrative work swallows the time you’d rather give them. Many educators respond by shifting from a teacher to a counselor, a role built around emotional and social support instead of lesson plans. The work runs deeper with each student and puts their wellbeing at the center of the day.
Changes like this rarely announce themselves loudly. They start as a small nudge you can brush off. Ignoring it gets harder as the months go by.
What purpose feels like
Most of the time it arrives quietly. A small exchange leaves you feeling like you were actually needed. You break down something complicated and watch it land. You steady someone who was spiraling. You point a person toward a way forward when they couldn’t see one. The tiredness afterward sits differently from the kind that flattens you.
Notice when you feel most switched on. Some people run best on targets, numbers, and systems that click into place. Others come alive guiding, backing someone up, keeping them going. Neither ranks above the other. They simply pull from different places.
Work that feels worthwhile usually reflects what you already care about. Value connection, trust, and steady growth, and a people-centered job will sit better than one measured purely in output. Perfection isn’t the goal. Honesty is.
Clues in your strengths
Patterns show up long before certainty does. Consider what people bring to you without being asked. Do friends start unloading before they’ve taken their coat off? Do colleagues mention how calmly you explain things? Are you the steady one while everyone else scatters like startled pigeons?
Pay attention to that. Support and guidance roles tend to grow out of qualities like these:
- Patience when someone needs time
- Empathy without absorbing everything
- Clear communication
- Real listening
- Steadiness under pressure
- Encouragement that doesn’t take over
Calling these soft undersells them. They carry weight because they help actual people get through difficult stretches. Technical knowledge can be added later. A steady, caring way with people is harder to teach, and having it already puts you closer to a new path than you might assume.
Why helping can grow
Roles built around helping tend to keep demanding more of you as a person. There’s no clocking in and ticking off a list. You get better at hearing what someone isn’t saying, at answering with more care, at reading people accurately. Growth like that outlasts any promotion.
Your motivation changes shape too. Pay and status stop being the whole scoreboard, and impact starts to matter. Did that person feel understood today? Did something hard get lighter because you were there? Questions like those keep the work from going flat.
None of which makes it effortless. The emotional load is real. Boundaries hold everything together, and so does proper rest. Choose a helping career with clear eyes, because meaning doesn’t cover lunch, sleep, or a life outside the job.
Testing the next step
Nothing has to be decided by next Tuesday. Small, low-stakes experiments beat dramatic leaps almost every time. Walk around in the shoes before entering the marathon.
Try a few of these:
- Talk to someone doing the job now
- Ask about ordinary days, not the highlights
- Volunteer somewhere support is the point
- Shadow a professional if you can arrange it
- Sign up for one course
- Note down what leaves you energized
Each one separates the imagined version from the real one. Occasionally a role loses its shine once you hear what the hours involve. Just as often, seeing it up close confirms what you suspected.
Stay curious rather than urgent. No contract is being signed. You’re collecting evidence, and evidence beats panic when a career decision is on the table.
Making change less scary
Fear arrives even when the change is a good one. Money, timing, family obligations, the thought of being a beginner again. None of that is irrational. Your brain is doing its job, protecting you, just with more theatrics than the situation calls for.
Size is usually the problem. “Should I change my whole life” is an unanswerable question, and holding it in your head produces nothing but dread. Narrow it until it becomes something you can act on this month. Build savings first. Find out what training actually requires. Set a six-month window and see what you learn inside it.
The fear rarely disappears entirely, and it doesn’t need to. It shrinks once the decision stops being one enormous leap and becomes a series of ordinary moves you can reverse if they don’t work.
Choosing a better fit
Borrowed definitions of success cause most of the trouble. Looking impressive while feeling depleted is a trade that stops paying off quickly. Your own version asks harder questions. Does this line up with what you care about? Does it draw on what you’re actually good at? Could you do it without performing a version of yourself all day?
Alignment matters more than ambition here. The goal is work that fits, that spends your energy well, that lets you be useful without straining for it.
That pull toward something more meaningful deserves attention rather than dismissal. Look into it. Give it time. The full map isn’t required. One honest step forward is usually enough to start.
Success Advice
How to Prepare for a First Video Conversation Online
A first planned video conversation feels easier when the technical setup and basic expectations are handled in advance. A few practical checks reduce distractions and leave more attention for clear, respectful communication.
Prepare Before the Conversation
Before joining a scheduled conversation through a service such as Aveola, review the meeting details, your account profile, and the subjects you intend to discuss. Early preparation prevents last-minute searches for links, passwords, headphones, or background information.
Confirm the Time and Access
Check the date, time zone, expected duration, and correct access link. Add the appointment to a calendar with a reminder, then open the platform early enough to complete any sign-in or permission requests.
Confirm that your email address or phone number is verified when the service requires account verification. Use a unique password and activate two-factor authentication when that option is available.
Plan a Few Topics
Prepare two or three simple subjects that fit the reason for the conversation. For a professional call, these subjects might include responsibilities, project goals, or next steps. For a social discussion, hobbies, travel, books, music, or daily routines provide comfortable starting points. Avoid writing a full script. Short notes keep the exchange natural while giving you a reference if the discussion pauses.
Check Your Connection
A stable internet connection supports clearer sound and smoother video. Close large downloads, cloud backups, streaming services, and unused browser tabs before joining.
The table identifies common connection issues and practical responses:
|
Issue |
Visible effect |
Preparation step |
|
Weak Wi-Fi signal |
Frozen picture |
Move closer to the router |
|
Busy home network |
Delayed sound |
Pause other high-bandwidth activity |
|
Outdated browser |
Missing features |
Install the current version |
|
Low device power |
Sudden disconnection |
Charge the device beforehand |
Set Up a Comfortable Space
The physical environment affects how clearly both people see and hear each other. Camera placement, light, sound, privacy controls, and personal limits deserve separate attention before the conversation begins.
Position the Camera
Place the camera close to eye level so your face remains centered without requiring you to look sharply upward or downward. A laptop stand, stable box, or adjustable monitor provides a better angle than holding a phone throughout the session.
Leave a small amount of space above your head and keep the lens clean. Look toward the camera while speaking, then return your attention to the screen while listening.
Improve the Lighting
Face a window or place a lamp in front of you, slightly above eye level. Strong light behind your chair creates a silhouette, while overhead lighting alone produces deep shadows around the eyes.
Review the preview screen before joining. Adjust the lamp, curtain, or seat position until facial details appear clear without excessive brightness.
Test the Sound
Use the platform preview or device settings to test the microphone and speakers. Speak at a normal volume and listen for echo, background noise, or distortion. Headphones reduce feedback when speakers sit close to the microphone. A quiet room with curtains, rugs, or soft furniture also limits reflected sound.
Protect Your Privacy
Review what the camera reveals before the conversation begins. Remove documents, photographs, screens, packages, or personal items that display sensitive information.
Five additional checks help protect your account and surroundings:
- Disable location details that are unnecessary for the session.
- Review camera and microphone permissions in the browser.
- Use a background blur when the room contains private material.
- Keep account recovery codes outside shared devices.
- Sign out after using a borrowed computer or tablet.
Privacy settings also control profile visibility, notifications, and contact options. Read each setting carefully instead of relying on its default value.
Set Personal Boundaries
Decide in advance which subjects and personal details remain outside the discussion. A planned conversation does not require sharing an address, workplace schedule, financial information, private documents, or account credentials.
Set a clear time limit when your schedule requires one. A simple statement at the beginning, such as having 30 minutes available, gives both participants a shared expectation.
Keep the Conversation Comfortable
Preparation continues during the exchange through attentive communication and a calm response to technical interruptions. A small problem with sound or video does not need to disrupt the entire session.
Communicate Respectfully
Speak clearly, allow the other person to finish, and ask direct questions when something is unclear. Muting the microphone during unavoidable background noise keeps the conversation easier to follow. Consent remains relevant throughout live communication. Respect a request to change the topic, pause, disable a feature, or end the session.
Finish With Clear Next Steps
Before leaving, confirm any agreed action, future date, document, or contact method. This step prevents confusion after professional, educational, or project-related discussions.
End the session through the platform controls, close unnecessary tabs, and verify that the camera and microphone are no longer active. A brief review of what worked gives you a stronger routine for the next conversation.
Success Advice
The Success Trap of Waiting Until Something Feels Wrong
After enough years in medicine, you start to notice a pattern that has nothing to do with biology and everything to do with psychology. The most driven, capable people in the room are often the last ones to deal with a problem.
Not because they are careless. Usually it’s the opposite. They have built successful lives by pushing through discomfort, solving problems, and staying in motion when other people stop.
I still think about one patient from time to time, although the truth is I’ve seen versions of her story more times than I could count. She was building a company, or maybe it was her career, I don’t remember anymore, and she’d been ignoring a symptom for months. She knew it wasn’t normal. She’d caught it early, but there was always a reason to put it off. A launch, a deadline, an important meeting she couldn’t miss. In her mind, stopping even for a day felt like falling behind.
By the time she finally came in, the problem had grown into something much harder to treat than it needed to be. I never thought of her as careless, and I don’t think denial is the right word either. She was doing what had always worked for her: keep pushing, don’t get distracted by small problems, and deal with them later.
That habit that serves you so well at work doesn’t always serve you everywhere else. When it comes to your health, it can become part of the problem.
Why Ignoring Small Problems Feels Like Discipline
People who accomplish a lot usually learn early on that not every ache, inconvenience, or setback deserves their attention. If they stopped every time something felt a little off, they’d never get anything done. After a while, pushing through just becomes second nature, and that habit doesn’t stay at work. It follows them everywhere else.
The problem is that this instinct doesn’t know the difference between grit and denial. Grit is choosing to endure something hard that you understand and have decided is worth enduring. Denial is ignoring a signal you never actually evaluated. They can feel identical in the moment, which is exactly why so many capable people confuse them.
This happens constantly, and not just when it comes to personal health. A founder notices the same customer complaints showing up every month, but keeps writing them off because fixing them would mean admitting there’s a problem with the product. An executive is surviving on four hours of sleep because it’s “just a busy season,” even though that season has lasted the better part of a year. Someone else has been living with the same symptom for months because making an appointment feels like one more thing they don’t have time for.
None of them are being careless. They’re using the same mindset that helps them succeed at work in a situation where it just doesn’t fit.
The Hidden Cost of Living Reactively
The real cost of reactive living isn’t the eventual crisis. It’s everything that happens before the crisis, which is usually invisible even to the person paying for it.
Living reactively means a portion of your attention is always spent managing something you haven’t dealt with yet. That’s a tax you pay daily, in the form of decisions made from a place of low-grade dread instead of clarity, in the form of energy that should be going toward your best work instead going toward keeping a problem contained. You don’t usually notice this tax because it doesn’t announce itself. It just quietly reduces how much of you is available for the things that matter.
This pattern plays out with health the same way it does in business. Very few of the serious conditions I’ve treated appeared overnight. Most started small, were easy to dismiss, and stayed that way for longer than people expected. Your body usually gives you plenty of chances to notice something is wrong before it forces you to pay attention.
Prevention Is the Highest Leverage Work You’ll Ever Do
Meanwhile, we celebrate the comeback, the turnaround, the crisis survived. Nobody publishes a book about the disaster that never happened because someone handled it early.
But prevention is the harder, more advanced skill. Crisis response gets you sympathy and a story. Prevention requires you to act on something before it’s demanding your attention, with no audience and no applause, purely because you understand what will happen if you don’t. That takes a kind of self-management that most people never develop, because it isn’t rewarded the way heroics are.
The best leaders and founders don’t actually handle crises better than everyone else, they just have fewer of them because they treat maintenance as a strategy rather than as something to get to eventually. They ask what a version of themselves with more information would already know, and then they go find that information instead of waiting for it to force its way in.
What This Looks Like in Practice
If any of this sounds familiar, you don’t need to turn your life upside down. Start small. Every few months, take a little time to think about the things you’ve been putting up with instead of dealing with. It could be your health, something at work, your finances, or even a relationship that’s been quietly wearing you down.
The most useful question to ask yourself is a simple one: Am I choosing to put up with this, or am I just avoiding it? Those two things can feel surprisingly similar when you’re in the middle of them, but they aren’t the same. One is intentional. The other usually catches up with you sooner or later.
A Different Definition of Strength
We tend to define strength as the ability to endure. I’d argue the more useful definition is the ability to notice early and act before you have to endure anything at all.
The people I’ve seen build businesses, careers, and even healthy lives over the long term usually aren’t the ones who can take the biggest hit. More often than not, they’re the ones who dealt with small problems before those problems had a chance to grow. It isn’t the most exciting approach or the one that tells the grandest story, but it’s the reason they stay healthy and keep moving forward.
Next time you brush off a small warning sign, ask yourself why you’re ignoring your body’s signals. Most of the time, you’ll likely find that it has less to do with your schedule and more to do with clinging to the identity of being someone who never needs to slow down.
Success Advice
How Teams Create Their Own Legacy Systems and How to Leave Them Behind
Legacy systems are not only old software left by someone else. Many teams create their own legacy after a fast launch. The product still works, but every change takes longer. People work hard, and delivery still slows down.This article explains how that happens, how to spot it, and how to plan a rewrite without stopping the business.
What a Legacy System Looks Like in Practice
A legacy system is software that costs more to change than it should. Age is not the main test. The real test is whether the team can still deliver at a normal pace.
Common signs are practical. The tech stack is hard for the current team to work with. Unused parts of the product stay in place because nobody is sure what will break. Tests exist, but they do not catch real problems. Only a few people understand how the system works. Small features take several sprints, and the team spends more time fighting the system than improving the product.
When effort goes up and output goes down, the system has become legacy for your team.
How a Fast Start Turns Into Legacy
Many teams do not inherit legacy. They create it while trying to move fast.
A common path looks like this. You need users quickly, so you build on an existing solution instead of starting from scratch. In the first months, that works. You ship. You get feedback. The decision looks smart.
Later, the same decision slows you down. The base system was not built for your roadmap, your team’s skills, or your quality needs. What helped you launch now blocks simple changes.Teams often stay with that base too long because the early result was real. Rewriting feels like throwing away progress. So they keep the old foundation even after it stops helping.
Why Teams Keep Patching
Most teams do not decide to live with legacy. They decide to make one more fix.
A patch looks cheaper and safer than a rewrite. It also avoids a hard discussion about stopping work on the current system. For a while, that can be the right call.
After a point, patches add more complexity than they remove. Each fix creates new constraints. The team spends its best time keeping the old system stable instead of building useful product work.
One clear signal is when a basic feature can no longer reach production in a normal cycle. There may be no major outage. There is just steady delay. At that point, the choice is usually simple: keep paying the cost of the current system, or test a rewrite under clear rules. If delivery has already stalled, some teams also need help to stabilize a software project before the next big decision.
Treat a Rewrite as an Experiment
A full rewrite can fail if it has no limits. Some rewrites never reach users and waste months. That risk is real. Staying in legacy forever has a cost too.
A better approach is to treat the rewrite as an experiment. Set a clear scope for the first version. Review progress every week with demos people can see. Track how much work actually gets finished, not only how busy the team looks. Keep the old system running until the new one is ready. Do not freeze the business while the team rebuilds in private.
This makes the decision easier to manage. Stakeholders can judge real progress. If pace and quality improve, continue. If not, stop before the rewrite becomes its own long project with no end date.
Describe the Product You Want Before You Rebuild
Many rewrite projects fail because the team copies the old system as it is.
Legacy code shows how the product works today. It does not always show why a feature exists, or which parts are leftovers from old decisions. If you rebuild only from the old code, you may also rebuild old bugs and unused paths.
A clearer method is to describe the product you want first. Who uses it. What should happen. What you will leave out. Write that down so business and engineering share the same scope. Then decide how to build it.
This matters even more when teams can generate code quickly. Fast output without a clear product description can create a new legacy system sooner. Speed helps only when the goal is clear and shared.
Keep the Old System Running Until the New One Is Ready
Leaving a legacy system does not mean turning it off on day one. Customers still need a working product.Keep the old system live while the new one is built and checked. Release small pieces that prove the new system works. Review quality and pace often. Switch when the new product can support real use, not when the plan looks good on paper.
The goal is a clean handoff, not a dramatic shutdown.
Conclusion
Legacy is not only software you inherit. It is often software your own fast start created.If the team is busy and delivery keeps slowing down, do not assume another patch will solve it. Look at the cost of staying. If a rewrite makes sense, run it as a short, visible experiment. Describe the product you want. Keep the old system online until the new one can take over.
The useful skill is noticing when the system that once helped you launch now blocks progress, and changing course before that cost gets worse.
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