As you get older, you realize that the wisdom you truly need in life is readily available through the people around you. This was the thought that was going in my mind when I started asking friends (some you have already met a few years ago through this column) to revisit some conversations we had and see how time has made them and their perspectives change. Imagine this series as sitting extremely close with a trusted friend and simply discussing life and everything in between.

Today, I have the pleasure of having a conversation with Ann Kristine Peñaredondo, a trailblazer in the Filipino freelancer space, and a trusted leader in digital marketing.

Thought Junkie: Hi Ann, it's been a while since we spoke. What has changed?

Ann: I remembered doing this with you in 2019. I couldn't believe I'd get to sit down with you again. I am always humbled and honored. I feel amused because I know there is always someone more remarkable who deserves this space, but I am here. So I hope to bring light as much as I can.

It's my 10th year working from home doing online work! I left the last 9-to-5 job on February 14, 2014. Oh my goodness, I just realized this now. It's a coincidence that you're interviewing me at this time.

Since the last time we spoke, I no longer have braces (12 years a slave! Deserves another article, haha!) I got Covid-19 even though I was the most cautious in my household.

I lost my father (I called him Papa) in 2021 due to surgery complications. It's the most complicated and challenging event of my life (and my family's as well). It allowed me to understand how emotions can be complicated. It also allowed me to also understand myself.

Just like everyone else, I continue to go back to the normal routine post-pandemic.

What are the things you wish you could tell your younger self?

You're not going to marry Richard Gomez, but you're going to be fine. (Hahahahahaha!) He's my childhood crush, by the way. I may have just revealed my age for that, but I don't care.

There are times in my life that I felt that detours happened because I did not have what it takes, or that it's not really for me. I would tell my younger self that the detours she experienced were actually redirections to the best path God has for her. Accept each detour as provision and protection from God. He is preparing me for my life's purpose.

In junior high, my guidance counselor said I could work in marketing and it felt strange. It was based on the career aptitude test that the whole batch took. It was like my whole soul wanted to protest. "What are you saying? What is marketing? I don't want to sell. I can't do that!" I told the guidance counselor that I wanted to be a news anchor in the future. (The Golden Age of Television! Hahaha!)

The guidance counselor gave me a photocopy of the test summary with the word "marketing" circled at the top of the page. I went back to the classroom confused; I really couldn't imagine myself as a marketer. I forgot about that moment and I took a Communications degree in college.

Well, fast-forward to now – I am a digital marketer. I have helped business owners and experts communicate their message to customers and potential audience through social media, email, and copywriting. Although my college degree is about communication, it was still aligned to what I was about to do.

The high school me was confused, but the present me found clarity.

Has your thoughts about success changed over the years?

Definitely. Once you become a "tita," everything changes. Hahahahaha!

My thoughts on success were way different thirty, twenty, even ten years ago. (Showing my age here!) Success used to be defined by meeting society's standards: wealth, fame, and the ability to obtain whatever you desired with those two things.

Success also for me, has deadlines (again based on world standards). Like, married by 25, have children after, traveled the world by 40, retired by 60, yada yada yada.

My dreams of success revolved around those thoughts.

Life has taught me that success isn't about having a lot of money, because honestly, it will never be enough. And yes, fame doesn't necessarily mean you're rich, or you'll become rich.

Having money and fame nowadays can show you the door. However, it doesn't mean you can stay in the room.

When I got thyroid cancer in 2013 (and last year), it was a turnaround. All of a sudden, all my thoughts of success could be out of the window! Imagine, everything that I planned could be poof, gone! If your life's on the line, it would be impossible not to stop and think, "Are these (success thoughts) all worth it?"

There are times when I say to myself, "Oh, so this is what success in this area of my life feels like. I thought I needed more," or "Okay, I have experienced this success. You know what? It's good, but it's not what I needed."

All I wanted, in the end, was a simple life.

As people grow older, they can gain various perspectives on success from their own experiences and others'. That is the best thing about growing older; those collections become wisdom.

I saw this in my email; it's from a subscription I am enrolled in. It says, "The secret to sufficiency isn't having everything you need. It's appreciating what you already have." I think that sums up my current thoughts on success now.

What is your definition of leadership? How has it changed as you've changed?

My definition of leadership has changed over time, just like my definition of success.

When I was younger, leadership for me was being strict and people following your orders. That's because I was a girl scout leader in my 4th grade. I learned that my leadership style wasn't good when a college classmate said she always followed me because she was afraid of me. I was like, "Okay, wait a minute, I won't have friends if I'd be like this."

When I was in high school, I considered myself an average kid. So to me, I look up to leaders who see the average people. If a leader is relatable, then I can put my support on that person.

For me, leadership is guiding a team because you know you are capable; that you have the heart to do so. But at the same time, you are humble enough to know when to give way.

I am the firstborn, and all firstborns are naturally authoritative. Before, in small or big matters, I thought I always had to take charge because that's just a part of who I am - the capable part.

However, it doesn't mean people will follow you just because you have the upper hand.

Later on, I realized that leadership is also about having the heart for it. Do I really desire to lead? Leadership should not be forced, or you'll end up tired and empty, probably lost to why you're leading in the first place.

Or is there someone else who could lead better than you? Leadership is also about humility - that there are others in the boat who can row better than you. Allowing them to lead can make a difference in how you lead as well.

I have experienced different types of leaders in my life. There are those who I will remember because they were so strict. At one point it's good; it instilled discipline and a good work ethic in me. (I mean you don't want to get scolded first thing in the morning at work, 'no?) But I remember them because I was afraid of them. I remember leaders who are relatable, patient, and "saw" me – that I can do good.

During my time working for a US company (I served as the Division Head for close to two years), one of my colleagues said, "You're good at what you do. But you have always shown how open you are to learning. You are humble enough to say if you don't know anything, even saying thank you. How can you do such a thing?" I told her, "Thank you. But one thing that I told myself time and again: I do not know everything."

Advice for those entering the workforce or feeling stuck in their career?

If you're stuck where you are – I feel I needed to address them first because I have been there recently – it's actually a good place. That's coming from a person who is so organized and is always planning ahead; weird, I know!

Brendon Burchard said, "Most great accomplishments were achieved by people who had no idea what they were doing." When I realized I was stuck where I was, I told myself that I would just show up. I studied again. I always read books (but not as a bibliophile as you. Jesus, could you explain to me how you read more than 10 books last month?!), so that's what I read. I wrote my thoughts in my journal. You will get unstuck - somewhere, somehow. All because you didn't stop showing up for yourself.

If you're entering the workforce, here's the truth for you: there is nothing that you and I still don't know at this point. Information is abundant. The skills I learned during the last decade because of studying and applying at work? You could have acquired that skill in just a few minutes.

What will set you apart is your character – your values, virtues, principles, and ethics.

Gary Vaynerchuck wrote a book called 12 And a Half. (Okay, I would admit, I have this book, but I haven't read it. I got a reading backlog.) According to book pitches, it's the 12 emotional skills that Gary credits with his success in business. That just goes to show that apart from skills, it's your character that would help you create your career path.

I mentioned earlier that I was a high school average kid. I still consider myself as such. I was never the best. But I got better because I am open to learning. I showed up even if I didn't feel like it (especially when I didn't like the job). I asked questions. I knew what I could do and not do. And even if it was difficult, I believed in myself. Your character can bring you places or leave you at the sidelines.

To know more about Ann, visit AnnKristine.com.