Why Intelligent Risks Shape Success: Lessons from My Career Across Top Organizations

Ever feel stuck, like you’re waiting for the perfect moment to take a leap—whether it’s starting a podcast, writing that newsletter, or publishing a book? Here’s the truth: there is no perfect moment. Waiting only feeds fear, and fear stops you from embracing intelligent risks—the ones that lead to growth, opportunity, and fulfillment.

In today’s post, I’ll walk you through key lessons from my experiences at some incredible organizations to inspire you to embrace those intelligent risks. Let’s dive in, starting with the most recent roles.

1. Untap Your Sales Potential with Tanveer Mostafa and Ian Koniak

• Key Lesson: Do One Thing and do it well.

I used to fall victim to shiny object syndrome, always looking for greener pastures. But I’ve realized every role, relationship, and company has ups and downs—there’s no “perfect” scenario. Embracing the season you’re in and focusing on what matters most helps you grow faster.

2. TriNet

• Key Lesson: The magic of in-office culture.

During our NYC office’s peak, we blended mentorship with massive action, creating an unforgettable environment. Public speaking events like Shark Tank sessions made me step outside my comfort zone. These experiences were nerve-wracking but incredibly formative.

3. Fortune

• Key Lesson: Build a brand people trust.

Fortune’s prestige is built on its annual rankings. I learned that being intentional and consistent with your efforts builds long-term trust, whether in journalism or enterprise sales.

4. Udemy

• Key Lesson: Own your niche.

Udemy’s brand as the go-to for technical learning was a masterclass in identifying a gap and filling it with excellence. The market rewards organizations (and individuals) who do this well.

5. CoachHub

• Key Lesson: Hire the right people.

CoachHub’s team consisted of kind, talented individuals. When you hire the right people, half the battle is won. Our work in leadership development attracted those who truly wanted to make a difference.

6. LinkedIn

• Key Lesson: Thoughtful design creates impact.

LinkedIn’s emphasis on mindful design—both in its platform and work culture—was eye-opening. While scaling a company has its challenges, LinkedIn remains one of the best-run organizations I’ve worked for, with over a million applicants each year.

7. Cheetah Digital (Experian Marketing Services)

• Key Lesson: A great leader makes all the difference.

Working with Adam Klein was a game-changer. His ability to listen and empower us made work enjoyable, and our Vegas Summit showcased what happens when business acumen meets fun.

8. Alphaserve Technologies

• Key Lesson: Networking is powerful.

Attending high-end events taught me the art of connecting and adapting to new environments. While being a chameleon isn’t sustainable long-term, it can introduce you to incredible people who eventually become lifelong friends.

9. SHI International Corporation

• Key Lesson: Work-life balance matters.

At SHI, the chill environment and low stress were refreshing. It taught me that while high-paying jobs often require sacrifice, some seasons in life are about enjoying the journey and building relationships—not just chasing the next big goal.

If you found value in these lessons, hit the like button, drop a comment, or share your thoughts below. Let me know if you’d like to hear more stories from my career journey across these amazing organizations.

#CareerGrowth #LeadershipLessons #IntelligentRisk #SalesStrategies #BusinessDevelopment #ProfessionalDevelopment #NetworkingTips #Inspiration #MindsetShift #PersonalGrowth #WorkLifeBalance #SuccessTips #EntrepreneurMindset #PublicSpeaking

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I’m going to share with you what I typed into Chat GPT so you can see the before and after to show you the process of how I go about writing my LinkedIn Newsletter Articles in the mornings.

What I typed into Chat GPT: Taking Intelligent Risks is one of my favorite core values when I was working as an Account Executive in the LinkedIn Learning division.

I think too many people don’t take enough risks in their lives.

Imagine if you have been thinking about starting a podcast, publishing that newletter article or wrote an amazing book that so many people would enjoy to read your creative efforts but you are afraid of what other people think of you.

In today’s article. I’ll share with you one takeaway from each of the organizations I’ve worked in past during more recent years in hopes of inspiring you to take more intelligent risks in your life.  I’ll go in reverse chronological order

1. Currently at Untap Your Sales Potential- I’m starting to understand the value of doing One Thing and doing it well in order to accomplish your goals. Being guilty of Shiny Obect Syndrome the Grass is certainly not greener on the other side. Take it from me. Every organization, every marriage, relationship, friendship, family dynamics will have its ups and downs. There is no such thing as black and white the reality is many, many shades of gray. Of course, certainly companies have trade offs and depending on your needs you may go through different seasons in life and embrace that as well. There is no such thing as perfect. Everyone and every company is trying the best they can with what they know.
2. TriNet- I’ve never forget the incredible in person culture we created in the NYC office during the prime years. We were all hustling grinding, and there were a perfect blend of mentorship, and taking massive action. Those were some of the most formative years and really speaks to the power of an in office culture that worked. I’m afraid there will never been times like that again. In some ways, that’s healthy because if we were being honest with ourselves we put way too much of our value in life based on how well we did at work. I do honestly believe that in your early years it is important to put in the time and cherish the relationships and growth lessons learned there.

Shark Tank was always some of the best memories being able to practice public speaking and presenting in front of your peers was nerve wrecking but so formative in so many ways.

1. Fortune- The power of having a household name and working on your brand. Fortune is clearly known for the Fortune Rankings- the largest and most profitable brands in the world are listed on Fortune where people can’t wait to see what number their organization lands in this year.

There is so much rich history in Fortune and I really understood the respect and intentionality that journalists put into their craft. It’s no different from folks at Untap Your Sales Potential and how much people put into becoming the best value adding Enterprise Account Executive they can be. Not only to take care of their family but be able to having their champions get promoted and implement change and transformation.

1. Udemy- having one thing you are really good at is key here. At Udemy we were known by all of the technical leaders as the go to place to learn the latest and greatest trends when it comes to technology. Sure, there were other things but when you develop a strong brand and fill a gap in the marketplace- the market rewards you handsomely.
2. CoachHub- this was the place I felt the most comfortable because of the caliber of people you are working with makes such a difference. We hired some of the kindest human beings out there and because we are helping with Leadership Development, Grooming High Potentials, and developing soft skills for managers- it attracts a certain type of individual who really wants to make a difference in the world. The lesson is when you hire good people- that’s half of the battle in terms of making a company run well.
3. LinkedIn puts a lot emphasis in embracing the world self and it’s pretty cool to think of all of the deep, insightful, thoughtful moments that happen there. Everything is designed for a reason- the interior design is world class and the just the little details that make an organization run well. With anything, when you become too big then sometimes you feel like a cog in a machine but overall its probably the best run organization I have ever been a part of which is why LinkedIn always gets over a million applicants over there.
4. Cheetah Digital aka Experian Marketing Services- This was fun because Adam Klein did a great job of hiring good people. We were always laughing everyday and that made the work hours go by so quickly. Adam knew how to enable you to do what you did best. He is such a good listener and when we had our Vegas Summit- it was a taste of what good life of what could happen when you commit to the craft of gaining business acumen and solving problems.
5. Alphaserve Technologies- This was the first organization where I saw the insane power of networking. I got to go to some of the coolest, classier events I’ve ever been to in my life. I saw how people are all trying to help each other and I saw the power of being a chameleon. Many self development guru say that’s not healthy but I do think there is a place and time to be able to fit in and learn from everyone else around you. I don’t think long think its sustainable strategy but you do end up meeting some interesting people who become your friends afterwards.
6. SHI International Corporation- It was the chillest and least stressful environment I’ve ever been a part of. We got to meet so many interesting vendors and I was lucky enough to be at the center of it all. It’s so cool to be a part of hyper growth environments. It was really close to Rutgers University so you end up getting a lot of recent graduates joining the company. I saw that work doesn’t have to be stressful in fact it can actually be enjoying. It’s true what they say- when you have a job that pays a lot- there is a reason why it pays a lot usually because not many people are willing to put in the sacrifice it takes to make that type of money. At SHI, we weren’t paid that handsomely compared to most jobs I’ve had afterwards but honestly the work life balance was amazing. It was basically like going to college again. There’s something to learn from that as well. In some ways it was the opposite of LinkedIn where you definitely feel the pressure to perform. There is a time and a place for everything.

If you enjoyed this, hit a like, post a comment saying more if you want me to shared more takeaways from my lessons having the privilege to work for so many great organizations during my very interesting career so far.