Lester Chng

Cyber CEOs Brand Strategist. I build your brand as you build your business. | Senior Cybersecurity Advisor | Author | Naval Officer | CISSP | 🇨🇦🇸🇬 |

You head a leading cybersecurity firm.
But your online presence doesn't reflect it.

In fact, being invisible is damaging. 

You understand the power of thought leadership.
You know LinkedIn shapes deal flow and adds credibility in the industry.
You just don’t have the cycles (or the copy) to share your expertise and experience.

You have stories worth telling.

The insights from being in the trenches.
The deep conversations with your ace teams.
The hard discussions with your clients. 

Don’t let this wisdom go to waste.

That’s where I come in.

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How we work together.

Profile & Positioning
=> Rebuild your LinkedIn profile so visitors see industry authority, not “another vendor.”

Content engine
=> Ghostwritten posts that leverage your insights and expertise into engaging LinkedIn posts. 

Outreach campaign
=> Targeted DM campaigns and audience-building strategies that build your authority and land you on podcasts and conference stages.

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You focus on growing your firm and protecting your clients.
And we will ensure the industry, clients, prospects, and investors can’t ignore it.

Let’s build the personal brand that commands the cybersecurity conversation and drives business.


Worked with global client portfolio 
- MSPs
- MSSPs
- Agentic AI SOC
- AI-powered GRC 
- Operational Resilience 

Senior Advisor, Financial Crimes Unit Exercises. BMO Fusion Centre

Execution of Financial Crimes Unit Exercise and Drill Program
• Design and execution of exercises and drills to operationalize the Financial Crimes Unit Fusion Centre
• Scenario creation and exercise execution for Information Security, Enterprise Fraud Management, Physical Security, and Global Crisis and Continuity Management teams 
• Providing effective challenge of incident response readiness through exercise observation
• Execution of enterprise-wide Purple Team Exercise


Cybersecurity Exercises: Purple Team, Ransomware, DDoS, Malware, Data Corruption, Data Breach, 3rd Party Incidents
Fraud Exercises: ATOs, Attack on Payment systems, Business Email Compromise, PII Breach
Physical Security Exercise: Active Assailant, Civil Unrest, Bomb Threats
Crisis Exercises: Disaster Recovery, Business Continuity, Operational Resilience, Fire Incidents, Natural Disasters, Utilities Disruption

Welcome to yr cyber flight simulator. 

I promise I won’t make u cry. 

The Cyber Range has been a faithful workhorse of Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

Incident response professionals, IT teams, municipal leaders, law enforcement officers, veterans, and foreign partners have gone through their paces at the range. 

Has yr team seen what a cyber incident looks like?

Have they been in the hot seat, trying to make sense of what’s happening and needing to coordinate and prioritise actions?

Have they been given the rigor of training to sharpen their instinct, rehearsal their articulation, and coordinate competitions priorities?

This is your cyber flight simulator. 

Step in and see what happens when the rubber hits the road. 

Or are you going to take the risk and wait for a real incident to find out?

Good luck. 
Godspeed. 


P.S 
Please follow Rogers Cybersecure Catalyst, Toronto Metropolitan University. 

We have been delivering exciting programs to individuals and organizations for years and have shaped Canadian’s Cyber Ecosystem. 

It’s going to be an eventful year. 

Follow + try to keep up w the Catalyst.

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I once received AAR feedback from an executive that changed how I view these "mundane" reports.

After-action reports are very important to the success of an exercise program. Without it, there is no chance of leadership buy-in, and soon the program will fizzle out.

These are typical uses/benefits of an AAR.

• capture lessons learned
• provide recap of proceedings
• serve as evidence for risk/auditors
• feeds into enterprise-wide action item register

On this occasion, I drafted the AAR for a fraud-related exercise. It involved many operational teams including executive involvement. The AAR was signed and sent.

One feedback from an executive stood out.

"It had alot of detail, but I don't know if it was a success".

That struck me. We just missed an opportunity.

An opportunity to highlight:
• the alignment with the overall security program
• the collaboration involved to run the exercise
• the advancement in teamwork 
• the reduction of risk

Include a clear story and highlight the win in your AAR.

Don't take these exercises and artefacts for granted.
Each event builds confidence, familiarity, and resilience.
Don't let it go unnoticed; give it its due credit.

P.S Have you seen AARs put to good use?

Most cyber CEOs think LinkedIn is about “posting more.”

It’s about posting with a positioning equation:
Authority + Trust + Leads

Don't start without a clear content strategy.

Here’s the simple way to build your content calendar.

𝗔𝘂𝘁𝗵𝗼𝗿𝗶𝘁𝘆
1. Build authority so you become the obvious expert.
Authority is when your audience says,
“This person knows the space.”

Teach one niche concept per post (one takeaway).

Share your lived experienced not conceptual ones.

Break down “why this fails” in real environments.

Add proof when possible:
Lessons, patterns, results, before/after.
Authority posts go deep in your niche.
More “results, insights, wisdom.” Less "frameworks"

𝗧𝗿𝘂𝘀𝘁
2. Build trust so people believe in what you stand for.
Trust is when your audience says,
“I’d take a meeting with them.”
It comes from clarity and consistency, not hype.

Show how you think, how you communicate risk, and how you make tradeoffs under constraints. Use stories, principles, and honest calls on what you will and won’t do. When people understand how you deal with situations, they start to trust your delivery.

𝗟𝗲𝗮𝗱𝘀
3. Generate leads without sounding salesy.

Direct: a clear CTA after you have earned it.

Indirect: a walkthrough of what it is like working w you.

Remove friction:
scope, timeline, roles involved, what success looks like.

Make it obvious you solve this specific problem for this specific buyer. Lead posts can be direct or indirect, and “walk-through” posts remove buying friction fast.

If you want a repeatable content calendar, stop brainstorming topics.

P.S Do you start writing without a plan?

Thanks Timothy Martens for prompt inspiration.

And Gerald Auger, Ph.D. + Mike Miller
for the reminder to include an image =)

How was your first full week at work?

This will happen if you don't intervene.

The Rule of the First 5 Days is a stock market indicator that states that if the market performs positively in the first 5 trading days of the year, there is a high probability that the markets will end the year positively.

Historical probabilities are between 69 - 84%.

Some of the reasons are:
Early Positioning
Investor Sentiment
Self-Fulfilling Prophecy


Bringing it back to how was your first week back at work?

Busy?
Stressed?
Juggling priorities?

Chances are if you don't make any changes, this will be how your year pans out.


If you had a great week, keep at it!

If not, time to review:
- the triggers
- the pain points
- the larger picture
- the longer term goals

Good luck for week 2!

P.S Dow has best 5-day start to year since 2006!

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bootcamp

Sign up here:
https://catalystcorporatetraining.classe365.com/form/view/AutoBootCamp?_gl=1*9rfqtg*_ga*MTQ4NTczNDM0MC4xNjk4MjQxODM1*_ga_YYXBQS6S5Q*MTcwNzgzMzEyNi4xODEuMS4xNzA3ODMzMTYwLjI2LjAuMA

Time is flying by. Jan is almost over. 

This is 1 thing I miss from 10 years ago. 


My lucious hair that would give me a chance at K-pop auditions. 

Just kidding. I stand no chance. 



What do u miss from 10 years ago?




Thanks sir Chris Chia for taking this pic and sending it again to me recently!

Leader, Coach, Facilitator

If your cyber exercise doesn't make you sweat,

why do you call it an exercise?

Too many teams are taking a stroll during tabletop exercises. They don't prepare in advance, they talk in circles, and frankly take it too lightly.

I have seen teams prepare extensively for exercises.

They relook their process and hold internal preparation meetings to validate if it still makes sense. They ask tough questions internally and the leaders confirm if their assumptions about alternatives, recovery times, capabilities, and priorities are still accurate.

The best teams go in well-prepared and respond confidently. This is not just for show. This is an opportunity where leadership teams have recognized the importance of readiness and set aside protected time to be intentional about preparation. 

This only happens if the exercise program is well-socialized.
When the experience and outputs are understood.
And the leadership is serious about training.

Otherwise, what's the point?
Check a box? It's 2026, do better.

Your next Cyber TTX will be miles better with this small tweak. 

Don’t rush the start of the exercise. 

I know you have been planning it for months. Your adrenaline is pumping and you assume the participants are chomping at the bit to begin. 

But don’t neglect the pre ex brief. 

Here’s why it matters. 

1. Not everyone is familiar w exercises

Some have never participated in one. 
Others can’t remember what it’s like. 
1 or 2 even have weird assumptions. 

2. Remind everyone of the Why

The stakeholders are not equally invested in the exercise or outcome. Half are wondering why they are there. 

3. A good start is important

Some exercises that start poorly can result in minutes of waffling, rabbit holes or just straight up disengagement. 

4. Questions forces a buy-in

Facilitate a short quiz or discussion. 
This makes participants feel involved and helps them warm up as well. 

5. Simple introductions helps

You will be surprised how often teams don’t know each other or what role they play in an incident. 
Take time to do a roundtable intro. 

6. Sponsor emphasis 

Allow the exercise sponsor to speak. 
This reiterates the investment, focus, and important of the exercise. 

7. Calms your nerves

Address concerns before an exercise can help mitigate against difficult scenarios such as wrong expectations and challenging stakeholders. 
There will also be disruption but touching on some issues early helps. 

The next time you plan yr exercise. 
Spend abit more time on the start. 
It will be worth it. 

P.S any other exercise faux pax?

What most Cyber CEOs post on LinkedIn 
 
- repost their company's post 
- post about the latest hack 
- random AI blog 
 
What should Cyber CEOs post on LinkedIn 
 
- customer success stories 
- lessons learned about your business 
- strong opinion about industry issues 
 
You are the leader. 
 
Lead by example. 
 
Here are more post ideas. 

Subject Matter Expertise
- insights
- pain-points
- transformation
- trends + opinion
- counter-trends
- mistakes you have seen others made

Trust
- client success stories
- decision-making dilemmas
- framework for decision-making 
- social proof
- results

Character
- guiding principles
- values
- client examples
- stories of resilience
- leadership

Authenticity
- challenges that excite you
- lessons learned
- challenges that you overcame
- best advice that you received

Majority of my bosses in Cybersecurity have been female.

Yet female only make up 21% of the cyber workforce.

I interviewed Sarah to get her insights on Women in Cyber.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗪𝗼𝗺𝗲𝗻 𝗶𝗻 𝗖𝘆𝗯𝗲𝗿 𝗟𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗣𝗿𝗼𝗴𝗿𝗮𝗺

1. When you think about women leading in cybersecurity, what have you noticed most often in how they lead, communicate, or navigate their roles?

They’re brilliant and discerning. They carry a full plate - navigating complex decisions and significant risk - and still, they lead with calm authority, thoughtfulness and integrity. They think deeply about their teams, their organizations, their families, and the broader systems. They’re the kind of leaders the world needs more of.


2. As you look ahead to the Women in Cyber Leadership Program in Malaysia with the Catalyst, what aspects of the program are you most curious or energized about?
   
After 4 years collaborating with the Catalyst to support cyber leaders from across Canada, I’m incredibly excited to connect with cyber leaders from 7 countries across ASEAN. It will be thrilling to be part of the conversation as these women come together to learn from and with each other.

 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. How are companies promoting diversity?

Soft Skills Expert • Certified Leadership & Public Speaking Coach & Facilitator • Program Design and Instruction @ U Toronto, KPMG, ESRI, Rogers • I help leaders transform confidence into connection and influence.

I trained Principle Warfare Officers. 

We assessed them on 3 attributes. 

The Principle Warfare Officer (PWO) was responsible for fighting the ship. 

This included the deployment of weapons, manoeuvres, and in many cases the control of multiple ships and aircraft to fulfil a mission. 

These are the 3 attributes. 

Knowledge 
- know the procedures 
- know the asset capabilities
- know the adversary’s capabilities 
- know the ever changing situation 

Command and control
- clarity of situation  
- clarity of instruction 
- clarity of orchestration

Creativity 
- demonstrates intuition 
- demonstrates flexibility 
- demonstrates adaptability 


In cybersecurity operations,

We assess
.
.
.
.
.

Hope you get my point. 

Happy training.

Most cyber CEOs aren’t afraid to post.
They’re afraid to be misunderstood.

And 19 other myths of writing on LinkedIn. 

 1. “I’ll get DMs from random people and waste time.”
 2. “If I post about a niche topic, it’ll limit my market.”
 3. “I should wait until my messaging is perfect.”
 4. “I’ll get fact-checked and embarrassed.”
 5. “I’ll be judged by peers in the industry.”
 6. “Clients will think I’m wasting time.”
 7. “I’m not a ‘social media' person.’”
 8. “I need a hot take every time.”
 9. “I’ll look like I’m bragging.”
10. “My team will cringe.”
11. “I need perfect writing.”
12. “People will think I’m selling.”
13. “I’ll attract trolls or get dragged.”
14. “I’ll upset a partner/vendor/client.”
15. “My competitors will copy my ideas.
16. “I’m not ‘big enough’ to have opinions.”
17. “If I post, I’m giving away the secret sauce.”
18. “Need to sound super technical to be credible.”
19. “If engagement is low, it means I’m bad at this.” 

P.S which is your fav? Mine is #8  🔥

I reviewed the LinkedIn headlines of 23 Cyber CEOs.

Not 1 mentioned these important aspects.

LinkedIn headlines are your first impression.
More precisely, the first 57 characters matter.

They are seen:
• on your profile
• during connection requests
• on the main feed via your posts
• in the comments with every response


I help [buyer] achieve [outcome] without [pain].

None of the CEOs mentioned buyer, outcome, or pain.

How would you write your headline?



[9]
CEO at [Company]
CEO at [Company]
CEO at [Company]
Founder/CEO at [Company]
Founder and CEO of [Company]
Founder and CEO at [Company]
Co-Founder & CEO at [Company]
Co-Founder & CEO at [Company]
CEO & Co-founder at [Company] - We are hiring!

[7]
CEO at [Company]| Autonomous SOC
CEO @ [Company]- Enterprise Hyper-Automation
Co-founder & CEO at [Company]| AI for Security Operations
Co-founder and CEO @ [Company] | Security Operations, at scale
Co-Founder/CEO at [Company]| Outpace attackers with agentic AI SOC Analysts
CEO @ [Company]| Executive | Entrepreneur | Revolutionizing the SOC with AI
Founder, CEO @ [Company] Autonomous SecOps & Investigation Platform with Hyperautomation.


[7]
Hiring misfits to solve security!
Tech Entrepreneur, investor and board member.
CEO at [Company] and Author of [Book] available now!
Building Your AI Knowledge Engine for Security Operations. Hiring!
Building great teams to execute on very difficult engineering problems
Tech Founder & Executive. Defender. Nation-state Hacker. Medal of Honor Recipient. Public speaker.
Empowering businesses: ChatGPT training, strategizing AI implementation, and offering tailored LLM and AI solutions for process automation.

AI tools are being used in yr org. 
Have your IR plans kept up?
Here are 4 changes to make. 

Implementing AI tools have left security team scrambling over the last couple of years to ensure it is securely deployed and monitored. 

Your incident response plans may have be neglected in the process. 

Consider these updates. 

1. Include AI related incidents 

- sensitive data exposure
- supply chain vulnerabilities 
- unauthorised model changes 

Don’t assume your plan is a catchall. 
AI asset owners don’t fully understand the security risks. 

2. Validate asset + contact list

- AI asset owners 
- data architects r crucial
- most of these folks r probably new

These AI gurus have been heads down focused on speed on implementation. They probably can’t spell cyber if u meet them for the first time on an incident call. 

3. AI specific containment

- understand the impacts 
- ask if traditional options will work

It’s going to get more complex as AI tools integrate across enterprise. It may soon become so entrenched that disabling it is a non option. 

4. Logs and investigation 

- review if current threshold is valid
- check on logs before/after go-live

You will learn to love “black boxes” and need to navigate round them. 


P.S what other areas to add?

2.

Incident response plans only play a small part in cyber resilience. 

“Do you have an IR plan?”

Is probably one of the most common question that consultants and experts use to gauge a company’s resilience. 

Many teams are happy to tick yes. 

But having a plan is merely the start. 

Here’s why:
- high turnover of staff
- fast pace of tech change
- lots of assumptions remain  
- plans get outdated due to new tech 
- teams don’t use the playbooks/plans
- primary teams hardly get trained
- secondary teams ignored 
- random cyber exercises 
- no training plan

There is barely any focus on training. 

7 men squads in the military get more training time and resources than multi-million dollar cyber defence teams protecting our financial ecosystem. 

Will having a plan alone save you?

And how long are you going to assumed your team is ready?

P.S the world is still a vulnerable place

Human skills training will unlock your career potential.

These are your advantages against AI... for now.

I interviewed Sarah to get her insights on human skills.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗛𝘂𝗺𝗮𝗻 𝗦𝗸𝗶𝗹𝗹𝘀 𝗧𝗿𝗮𝗶𝗻𝗶𝗻𝗴

1. What are some of the key human skills that will unlock an individual’s potential in the workplace?
   
First: self-awareness, because awareness always precedes change. From there, the skills of emotional intelligence, listening and clear communication. These will help you improve your relationships and increase your influence and impact.


2. Were there pivotal moments from your own experience or from those that you coached that reaffirm that Human Skills Training is a vital part of career development?

I’m reminded of this everyday, given how easy it is to outsource one’s thinking, ideas, and voice to AI. We’re constantly pitched the benefits of efficiency, when really it’s our unique essence as a human that makes us compelling. Human skills will always be vital to professional and personal development.  


If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. Are you worried about AI impacting yr career?

5 LinkedIn posts that should be part of your pre-RSAC marketing plan. 

If your Head of Marketing is not bugging you to start posting on LinkedIn before RSAC, ask them why?

Even better if they tell u what to post. 

Here’s 5 posts that I will write. 

“Heading to RSAC next week. Here’s the one question I’m asking every CISO I meet.”

“One year ago, [Client Type] was struggling with [Specific Problem]. Here’s what changed.”

“Everyone’s talking about [Trending Topic] at RSA. Here’s what they’re missing.”

“We’re bringing [Specific Thing] to RSA. Here’s why we built it.”

“I have 8 meeting slots open during RSA. Here’s who I wld love to talk to.”

_____________

Here’s 3 reasons why you shld post. 


REASON 1: 
Conferences are chaotic. 

This gives you a chance to cut through the noise.  

REASON 2: 
Post-Conference follow-up success is built upon pre-conference interaction.  

Unless you are a magician and can engage random folks on the floor. 

REASON 3: 
Yr competitors are already doing so. 

Silence = Falling Behind

You don’t want to waste all that $$$$

———————

No time to write?
Overwhelmed by the preparation?
Rather spend time on client demos?

Let’s work together and take that off your plate.

LinkedIn posts can be complicated.  

I simplify it by 3-2-1 method. 

3 types of posts 
- authority 
- leads 
- trust

Cycle this through the week. 

2 content pillars
- cybersecurity exercises
- LinkedIn copywriting 

Alternate pillars per day. 

1 target audience per post

Focus on 1 reader. 


What’s your 3-2-1?
⬇️

People judge within 7 seconds of opening yr mouth.

That's why I still get nervous before every presentation.

I interviewed Sarah Lang to get her insights on public speaking and establishing leadership presence.

Sarah is a certified coach, facilitator, and founder of the Human Skills Leadership Lab, a unique and customizable program that helps professionals develop the human skills (or ‘soft skills’) required for effective leadership in the modern workplace. 


𝗔𝗰𝘁𝗶𝗼𝗻𝗮𝗯𝗹𝗲 𝘁𝗶𝗽𝘀 𝗳𝗼𝗿 𝗹𝗲𝗮𝗱𝗲𝗿𝘀𝗵𝗶𝗽 𝗽𝗿𝗲𝘀𝗲𝗻𝗰𝗲

1. How would you explain what leadership presence is for those looking to grow in their career?
   
Leadership presence is your ability to stay grounded and intentional in all moments - including when you’re under pressure. In a society driven by distraction and dopamine hits, leaders who embody this type of presence, steadiness and self-trust stand out.  


2. What are some ways to practice being more grounded and present?

• Spend time on analogue hobbies that anchor you to the physical world - art, books, gardening, cooking, etc.
• Practice mono-tasking on purpose.
• Try slowing down your communication - listening, speaking, pausing, saying less.
• Regulate your nervous system with breathwork, yoga or grounding activities.
• Carve out daily moments to pause and transition between meetings and events


3. Presenting to an audience is a real fear for many professionals. Do you have a couple of tips that you usually teach?
   
First, get crystal-clear on what you’re trying to say and why it matters to your audience. Then, practice your vocal and non-verbal delivery to make sure you sound like you care about what you’re saying! I also teach simple ways to work with nerves rather than fight them so speakers can stay connected to themselves and their audience.
 

If you enjoyed this interview series, please follow Sarah Lang (MA, PCC, CPCC). She is a human skills expert, a Leadership in Communication Skills Coach, and has trained leaders from leading corporations and brands.

P.S. What's the best advice u received on public speaking?

Most Cyber CEOs post randomly and wonder why LinkedIn isn't working.
They write when inspiration strikes.
They share whatever feels right in the moment.
They post about the latest breach one day, their product the next, then go silent for weeks.

The result? Confusion. Zero traction. Wasted effort.

Here's what you should be doing instead:
Plan your content around 3 post types.

1. Authority posts
This is where you demonstrate expertise.
Share insights from client engagements. Dive deep into problems you're solving. Break down complex security concepts.

Examples:
"5 issues all enterprises face with AI governance"
"How we helped Company X reduce risk by 40%"
"The biggest misconception about Zero Trust"

These posts establish you as the expert in your niche.

2. Trust posts
This is where you build relationships.
Share your founder journey. Talk about team culture. Reveal the challenges you've overcome.

Examples:
"Why we started this company in 2019"
"The toughest decision I made as CEO"
"What our clients don't see behind the scenes"

These posts show the human behind the solution.

3. Lead posts
This is where you attract prospects.
Address pain points directly. Show transformation. Make your solution crystal clear.

Examples:
"Overwhelmed with compliance requirements?"
"How we saved a client 2000 hours per year"
"Is your board asking about AI risks?"

These posts turn readers into conversations.

Now here's the system:

Mon: Authority post
Wed: Trust post
Fri: Lead post

Repeat this for 6 months minimum.
Map out topics under each category. 
Populate your calendar. 

Never start from a blank page again.

Most cyber CEOs will read this and do nothing.

They'll keep posting randomly.
They'll keep getting zero results.
Don't be most CEOs.

Plan your content. Execute consistently. 
P.S. What type of post do you struggle with most?

Worried about the removal of your role?
Don't be a deer in headlights.
Do this immediately.

2025/2026 is the new 2020.

The trigger is different.
Lockdown vs AI.
The outcome is becoming the same.

And we shouldn't really be surprised...
If you are, stop living under a rock.

What did you think would happen?

Just look around the wider workforce, companies, tasks, processes, meetings, discussions, emails.....

Bots will be much better at most of that.

Thanks Sherlock, so is that the end for the human worker?

Maybe.... but not yet.

So, until we start serving robotic overloads, let's prepare and control what we can.

These are 5 things I'll immediately do to mitigate job risk.

1. Get better at your work

Thanks, Captain Obvious.
You are welcome, but I made Major.

The people who are most worried are probably the ones with the most areas to improve...so if there was a time to buck up, its now.

Say yes more than no.
Spend that extra hour.
Put in that additional effort.
Put yr hand up for that project.
Capture your achievements.
Socialize the wins w teams.
Help other teams win.


2. Restart your network

Your Rolodex is creaky, I know, but it is time to revisit.

It will be awkward at the start, but keep at it.
Better now than when you "need" a job.

Pro Tip: Be genuinely interested in them

Your older connections are easier to rekindle than establishing new ones. 


3. Build your profile

Refresh and improve your LinkedIn profile + professional portfolio.

It's 2026, we go to your profile and website if we want to get a good sense of who you are.

How are you showing up?
• old dated profile pic
• high school quality about section
• boring as f experience description

Or are you invisible?
Makes sense if you are James Bond.


4. Grow your network

Do some research. 

Who are your peers?
Who is in your dream role?
Which are the interesting companies?

Some of the folks who reported to you may now be execs.

Don't wait till your need a network to build one.

The earlier you start the better.

What are you waiting for? The HR Call?



5. Think like an owner

This is the future of the worker.
Gone are the days of 40 year old career.
My mom celebrates 45 years at 1 company soon!

If you think like an owner, you stop waiting for permission.

You start taking action, owning the risks, and keep going.

What is one thing you think will change when there is this mindset shift from employee to "owner worker"?

Career Strategist I Change advisor for Leaders | I help successful professionals build freedom, income & impact through portfolio careers | Speaker I Ex-Citi COO | Follow for modern leadership, career and change

Over the past 25 years, I have built a successful international banking career.
Most recently, I was the Regional COO for Citibank’s $2Bn business across 16 countries in Asia - leading large-scale transformations in digitisation and culture.

But in 2021, I walked away from my high-paying executive role.

Why?

Because I wanted more space.
More time with family.
More alignment between who I am and how I work.

But I didn’t want to start from scratch.
So I asked myself a question:
What if I could build a career around everything I already know - and love?

That’s how my portfolio career began.
And it changed everything.

Now, I help other professionals do the same.

What I’ve built since 2021:
→ A 6-figure portfolio business with 3 income streams
→ Founder of Change is Possible - a business community for professionals redesigning their next chapter
→ 100K+ LinkedIn followers (grew from 17K in under a year)
→ Coached 100+ professionals through successful career transitions
→ Host of a Top 20 global podcast on career change, Change is Possible
→ TEDx speaker, Forbes columnist, and Bloomberg TV guest

Want to build your own portfolio career?
🚀 THE PORTFOLIO CAREER ACCELERATOR (Launching January 2026) 
Apply here: https://docs.google.com/forms/d/1thkmph_EwRxLGfuL9muCsRir1uKDdF2nXYeI7X_1oSA/edit

This is an 8-week program designed to help you:
→ Turn your expertise into income
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→ Create your first income stream - even before you leave your job

Only 20 spots. 12 already claimed.

Other ways we can work together:
✔️ Join my business community — Change is Possible https://changeispossible.co.uk/ - doors open for new members on Sept.10, 2025
✔️ Book me to speak — I deliver keynotes on leadership, change, career reinvention, and the future of work - send a DM.
✔️ Hire me as an advisor — I support companies navigating complex transformation - send a DM to meet and explore.
✔️ Book 1:1 coaching — For senior execs ready to design their next chapter - send a DM.
✔️ Book my LinkedIn Growth Bundle — A 2-session intensive where I teach you the exact system I used to grow to 100K+ followers. Apply here: https://docs.google.com/forms/d/1bLp7wmK8xhIpfFu8beImvD5JZQHYsbraTBx5Orjx0zs/edit

P.S. Still wondering if change is really possible?
🎧 Tune in to my podcast Change is Possible — where 100+ professionals share how they redesigned their careers and lives. Watch here - https://www.youtube.com/@ChangeIsPossiblePodcast

Ani Filipova

Scrolling LinkedIn, you will think everyone is operating at 100% every day.

5 am routine ✅
10 client calls ✅
Launched 3 products ✅
Ran a marathon ✅

Meanwhile, I'm over here thinking:

• My video production is weeks behind
• I have zero content prepped for this week - I'm creating as I go
• That Substack I promised myself I'd launch in January is still in drafts
• My follow-up list has a follow-up list

And you know what?

My business is still growing.
My Portfolio Career Accelerator starts in 10 days - with brilliant people already inside.
My community is thriving.
My podcast just passed 30,000 subscribers.

Nobody posts the hard days.
But those are the days that matter the most.

They teach you:
• Perfect doesn't exist
• Decisions get made with incomplete information
• Momentum matters more than intensity

That's why I didn't build my Portfolio Accelerator as a blueprint for perfection.

I built it as a framework for sustainable progress.

Because the move from corporate to a portfolio career isn't about doing everything right.
It's about continuing when nothing feels right.

Sustainable success isn't showing up at your best.
It's showing up anyway.

Some days you are on fire.
Some days, you are just keeping the fire from going out.

Both count.
Both compound.

If you are ready to build a portfolio career that works with your real life - not some imaginary perfect version of it - applications for the Portfolio Career Accelerator close soon.

A few final spots remain. Apply here: https://lnkd.in/gpEqqqFs

We start in 10 days.

Build something that survives your ordinary days.

Follow me, https://lnkd.in/g6R7Yb8t, for daily doses of career, leadership and change truths

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Image credit: Jen Blandos

If you followed every piece of “good career advice” you were given, you would be less employable today - not more.

I was repeatedly warned that changing roles this often would destroy my career.

It turned out it didn’t.

They called it professional suicide.
Now I teach executives how to do it deliberately.

19 job changes.
5 countries.
25 years of “destroying my career.”

When I left my first job after 15 months, my mum was appalled.
Stability was everything to her generation.

Two years later, I left again.
Then again.

At Citi alone:
10 role changes.
5 countries.
21 years.

Every move came with the same warnings:

“You are ruining your CV.”
“No one will trust someone this unstable.”
“You’ll regret this later.”

And there were moments I wondered if they were right.

I watched peers climb neat ladders while my path looked… messy.
Hard to explain.
Easy to judge.

At 50, I walked away from a COO role and started again.
That’s when the concern turned into outrage.
People never understood the audacity to want something different.

Here’s the mental model most people miss:

• One skill = one solution
• Two skills = multiple options
• Ten skills = leverage from angles others can’t see

Experience doesn’t add up.
It multiplies.

Today’s market doesn’t reward narrow specialists who need the world to stay predictable.

It rewards people who can:
→ Connect dots across functions
→ Solve problems from multiple lenses
→ Rebuild themselves without panic

A “messy” career isn’t a liability anymore.
It’s optionality.

In a world that reinvents itself constantly,
your ability to change IS your stability.

That’s why I now help experienced professionals turn unconventional paths into:
income, 
impact, 
and freedom - without starting from scratch.

The Portfolio Career Accelerator starts January 26.

20 people.
8 weeks.
A clear system for turning what you already know into a career that compounds - a portfolio career!

10 places remain.
Apply here: https://lnkd.in/g8bpRmYN

Most people don’t need a new career.
They need a better way to frame - and monetise - the one they’ve already lived.

♻️ Repost this for someone still apologising for evolving.
→ Follow me, Ani Filipova, for daily career and change truths.

No one can ruin your day.

Unless you let them.

Most people think their emotions are caused by other people or events.

“They made me angry.”
“That ruined my day.”
“I had no choice.”

But that’s not how it actually works.

Nobody makes you angry.
You choose anger as the response.

That choice happens fast, but it’s still a choice.
The most underrated skill in life and business?

⚠️ Emotional control.

Not suppressing emotions.
Not pretending you are calm.
But responding instead of reacting.

Here is a simple framework I use when I feel triggered:

1️⃣ Name the emotion
Say it out loud or in your head: "I'm feeling frustrated."
Naming the emotion reduces its intensity by up to 50%.
You can't control what you don't acknowledge.

2️⃣ Delay the response
Wait 90 seconds before responding. 
Emotions trigger a chemical reaction in your body for only 90 seconds.
Anything beyond that - it is you feeding the story!

3️⃣ Reframe the situation
“What response helps me win long-term?”

This approach applies everywhere:

Before replying to a passive-aggressive email
Before reacting in a meeting
Before saying something you’ll regret later

Calm people don’t have fewer problems.
They just solve them better.

Your reaction is your responsibility.
And emotional discipline compounds faster than motivation.

♻️ Repost this for someone who needs the reminder.
→ Follow me, Ani Filipova, for more on leadership, career, and change.

Image credit: A.G.E on Pinterest.

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Skills don't predict performance. 

Character does.

I once hired the most qualified candidate on paper. 
Impressive CV. Perfect experience. 
They quit in 3 months.

The problem is that most interviews rely on rehearsed answers to predictable questions.

Here are 10 "non-predictable" questions that reveal who someone really is:

1. If money wasn't an issue, what would you choose to do for work?
→ Reveals intrinsic motivation vs. external rewards

2. When was the last time you felt proud at work—and why?
→ Shows what success truly means to them

3. What would you do if you knew you were going to miss a deadline?
→ Tests accountability and honesty under pressure

4. What do you think you owe an employer—and what do they owe you?
→ Exposes work ethic, expectations, and entitlement

5. What are your strongest strengths—and the weaknesses you're actively working on?
→ Reveals self-awareness and growth mindset

6. What's a belief you hold that most people disagree with?
→ Shows independent thinking and confidence in values

7. What do you do when you strongly disagree with your manager?
→ Reveals emotional intelligence and conflict maturity

8. If you could change one past decision, what would it be—and why?
→ Tests reflection, learning, and accountability

9. How do you handle working with someone you don't like?
→ Assesses professionalism when emotions are involved

10. Tell me about a decision you made that disappointed people.
→ Reveals leadership courage and ethical reasoning

Most bad hires don't fail because they lack skills.
They fail because their character was never tested.

📌 Save this for your next interview.
♻️ Repost this with someone building a team in 2026.
→ Follow me, Ani Filipova, for leadership, career and change insights.

Use these in your hiring process

I spent 20 years in banking, thinking I understood how the world worked.

Then I moved from Singapore to Hong Kong to become a COO, and as we began setting up our life again, I realised something uncomfortable:

I’d been living in a professional echo chamber.

My friends were bankers.
My network was bankers.
My entire view of “career” was shaped by one industry and one employer.

I didn’t even realise how limited my perspective was.

I was making decisions - about work and life -
based entirely on my own small bubble,
surrounded by people just like me.

And that’s when it hit me:

I was doing the exact same thing with my career.

I was looking at my future through a banking lens.
Surrounded by banking people.
Measuring success by banking standards.

I had no idea what else was out there.

Not because the opportunities didn’t exist.
But because I wasn’t in rooms where anyone talked about them.

The creator economy?
Never heard of it.

Portfolio careers?
Didn’t know that was a thing.

Multiple income streams?
Honestly, it sounded like a scam.

I genuinely believed my options were:
→ Stay in banking
→ Move to another bank
→ Or try consulting company

That was it.

The problem wasn’t fear.
It was visibility.

When everyone around you is on the same path..
That path feels like the only one.

So how do you break free?

1️⃣ Get outside your bubble 

Find one person doing work that fascinates you but seems "impossible." Talk to them. You'll be shocked how possible it actually is. 

2️⃣ Audit your inputs

Whom are you following? What are you reading? If it's all corporate content, you are trapped in an echo chamber. 

3️⃣ Take one small step into the unknown 

Attend an event outside your industry. Message someone in the creator economy. Learn about one business model you've never heard of.

The moment you step outside your professional bubble,
you realise the world is far bigger than what you’ve been shown.

That’s why I created the Portfolio Career Accelerator.

To show you the massive world of opportunities you can’t see yet,
and guide you if you decide to explore any of them.

We are starting Jan 26, 2026.
A few spots are still open. Apply here: https://lnkd.in/gpEqqqFs

or

👉 DM me and let's talk

Most career advice about “staying relevant” is useless.

People tell you to “keep learning”, “stay curious”, or “embrace change.”

Great. 
Super helpful.
I’ll just add that to my list right after
“drink more water” and “get enough sleep.”

Here’s what actually works - and you can start building it today, at any stage of your career.

It’s called being "T-shaped."

And if you are not developing this right now, you are quietly making yourself obsolete.

After watching careers stall, pivot, and accelerate at every level, this pattern shows up every time.

𝗪𝗵𝗮𝘁 𝗕𝗲𝗶𝗻𝗴 𝗧-𝗦𝗵𝗮𝗽𝗲𝗱 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗠𝗲𝗮𝗻𝘀

Think of the letter T.

• The vertical bar = depth.
Deep expertise in one core area.
What you are known for. What people trust you with.

• The horizontal bar = breadth.
Adjacent skills. Not mastery - just enough to connect dots, make better decisions, and create leverage beyond your lane.

What this looks like in practice:

➡️ Software developer
Depth: AI
Breadth: UX, delivery, business context

➡️ Marketing professional
Depth: campaign strategy
Breadth: data, psychology, financial thinking

➡️ Senior leader
Depth: decision-making
Breadth: technology trends, data literacy, change

➡️ Portfolio careerist
Depth: executive coaching
Breadth: content, products, community, speaking

This is why T-shaped people win.

Specialists struggle when their niche dries up.
Generalists struggle to stand out.

T-shaped people adapt.
They go deep when required 
and zoom out when it matters.

And if their depth becomes redundant (which happens more often than people admit), they don’t panic.
They pivot from a position of strength.

How to Build Your T-Shape (Without Overthinking It)

➊ Know your T
Be honest about your depth and your gaps. Most people are either an “I” (all depth) or a “—” (all breadth). Both stall careers.

➋ Use the 80/20 rule
80% of your effort: deepen your core skill
20%: build adjacent skills that compound it

Depth gets you hired and gets you projects.
Breadth gets you promoted and paid differently.

➌ Don’t dilute your edge
Breadth only works if your depth stays sharp. 
If your core skill slips, rebalance and go deeper before going wider.

𝗧𝗵𝗲 𝗕𝗼𝘁𝘁𝗼𝗺 𝗟𝗶𝗻𝗲

You don’t future-proof yourself by predicting the future.
You future-proof yourself by becoming someone who can adapt to any future.

And that’s exactly what a strong T-shape gives you.

If you are ready to build a portfolio career with both depth and breadth - combining personal branding, monetisation, speaking, board and fractional opportunities, wealth creation, and AI leverage - the Portfolio Career Accelerator starts January 26, 2026.

10 spots are already filled.
10 remain.

Apply here: https://lnkd.in/g8bpRmYN

------
In my newsletter today, I break this down in more detail. Subscribe here: https://lnkd.in/gzDCH9t9

In 8 days, we go live with The Portfolio Career Accelerator.

I’ve been planning this accelerator for the last 6 months - and it’s finally here.

Not as a course you “consume.”
But as a transition you actually make.

My goal is simple:

• Show corporate professionals the opportunities they are missing
• Build a bridge from corporate expertise to multiple income streams
• Be the translator people need - someone who speaks both corporate and creator

Because most professionals aren’t stuck. They are just operating inside a very small bubble and the accelerator will show them what is outside it.

This is an 8-week program, built around the 5 principles of a portfolio career, plus how to use AI to implement faster - not someday, but now.

Here’s how it breaks down:

Module 1: Build Your Brand & Audience
LinkedIn optimisation, content strategy, high-performing posts, lead magnets, newsletter creation

Module 2: Create Your Products
Turn expertise into courses, workshops, and programs. Pricing, sales process, launch strategy

Module 3: Become a Speaker
Craft keynotes, master delivery, build a speaker kit, and land paid gigs

Module 4: Advisor / Board Member / Fractional Exec
Shift from doer to advisor. Structure engagements. Find and land real opportunities

Module 5: Become an Investor
Investment fundamentals, portfolio building, diversification, and working with brokers

Module 6: Leverage AI
Prompt engineering, custom GPTs, AI agents

And you are not learning from me alone.

We’ve brought in incredible guest trainers - experts in their fields - speaking, investing, advisory, board and AI.

We start on January 26th.

And we already have amazing professionals signed up and ready to start. 

This cohort is capped at 20 people.
Why?

Because this isn’t passive learning.
It’s a transformation - with guidance, accountability, and a room full of people who get it.

If you are tired of living inside a professional bubble…

If you know there’s more available to you than one job title…

If you want someone who’s actually done this to show you how…

👉 Secure your spot here: https://lnkd.in/gpEqqqFs

8 days until we start building your portfolio career.

Let’s go.

♻️ Repost this to help another corporate professional see what’s possible
💾 Save this if portfolio careers are on your 2026 radar

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