Introduction
The career path isn't a straight line, and few understand that better than Tobi Oluwole. From selling hoverboards on campus to launching ThreeSkills, Tobi’s story shows the power of being intentional, flexible, and bold. In today’s highly competitive 2025 job market, Tobi’s insights aren’t just inspiring — they are essential.
In this post, we explore key lessons from Tobi’s career journey, his tactical advice for job seekers, and his philosophy on building a fulfilling life through meaningful work.
Defining Your True End Goal
Tobi’s career didn’t start with a perfect plan — it started with selling hoverboards to classmates. Over time, he realized that success wasn’t about a specific title or salary figure. It was about designing a life that matched his deeper personal values: freedom, presence for loved ones, and generosity. To get there, he made the strategic decision to transition into tech through a role at Shopify, despite the hurdles and rejections he faced along the way.
Tobi recommends every professional begin by envisioning their ultimate life goals — not just their next job title. Writing your own eulogy may seem morbid, but for Tobi, it created crystal clarity. Instead of blindly climbing a corporate ladder, he mapped each move against a larger personal vision.
If you’re navigating your next career move in 2025, stop thinking only about "the next job." Ask yourself: Where do I really want to end up, and why?
Digging Deep with the Five Whys
Many professionals stop their career planning too early. They think, "I want to be a senior manager" — but never interrogate why. Tobi’s advice: dig deeper. Use the "Five Whys" technique to uncover the real motivations behind your goals.
For example:
- Why do I want to be a senior manager? → To earn $200,000.
- Why do I want $200,000? → To afford a better home.
- Why do I want a better home? → To raise a family in a good environment.
- Why do I want to raise a family this way? → To leave a meaningful legacy.
Once you understand the real "why," you can creatively explore many possible paths — not just one narrow option. You also avoid building your entire life around chasing a job title that won't actually fulfill you.
Career navigation in 2025 is about alignment, not just achievement.
The Power of Micro-Pivots
If you have a big dream — whether that’s entrepreneurship or landing an executive leadership role — it’s unlikely to happen in one leap. Tobi believes in “micro-pivots”: small, strategic moves that bring you closer to your ultimate goal while gaining experience, skills, and network credibility along the way.
When he wanted to leave sales, he didn't quit overnight. Instead, he transitioned into customer success at Shopify, a role that leveraged his people skills but didn’t depend on selling unproven products. This pivot became the springboard for his entrepreneurial leap years later.
Job seekers in 2025 should embrace this strategy. Don’t get discouraged if your next role isn't perfect — think about whether it’s a strong stepping stone.
Building Genuine Relationships, Not Just a Network
In the current market, opportunities travel through people — not postings. Tobi’s philosophy is simple: relationships beat résumés. He advises professionals to focus on connecting, not just networking.
For a deeper dive into the modern networking techniques that are helping candidates stand out in 2025, check out this guide to Modern Job Search Strategies for 2025.
His key strategy:
- Compliment their "baby" — acknowledge someone’s business, career accomplishment, or recent success.
- Be curious — ask how they achieved it.
- Be genuine — share your story when asked, but focus first on them.
This method builds trust and goodwill, making you someone they want to recommend. In a world where jobs are filled before they ever get posted, becoming top of mind is a career superpower.
If you want more guidance on relationship-building and networking strategies that actually work in 2025, check out our Ramped Autopilot Program — and use code GETTHATJOB100 for $100 off.
Hire Yourself First
Waiting for permission is a mistake, especially now. If you can’t land the perfect job immediately, Tobi recommends you “hire yourself.”
This doesn’t mean launching a startup overnight — it can be as simple as:
- Running a project for free.
- Consulting for small businesses.
- Teaching skills you already know.
When Tobi couldn’t find a company that would give him the ideal growth platform, he started ThreeSkills. It wasn't instantly profitable, but it was real. It built credibility. It gave him experiences he could list on his resume and discuss in interviews.
In a tight 2025 market, waiting passively will only put you further behind. Create momentum for yourself — show initiative, not just intent.
Understanding Your True Value
Another mindset shift Tobi emphasizes: your paycheck is a discount on your real market value.
Companies must profit off of employees. If you’re paid $50 an hour, it’s because you’re creating $250–$500 in value per hour.
Knowing this, you can start exploring side hustles, consulting gigs, or small businesses where you capture more of your true worth — not just what an employer offers.
Platforms like LinkedIn, Upwork, and emerging AI-driven freelance networks are making it easier than ever in 2025 to find contract work, side projects, and alternative income streams.
Start thinking beyond the "full-time or bust" mindset.
Mastering the Modern Job Search
The 2025 job market has shifted:
- Companies often fill roles through referrals before posting.
- Recruiters are flooded with applications and lean heavily on internal networks.
- AI is screening candidates at a higher rate, making personalization more critical than ever.
Tobi’s practical advice for navigating today’s search environment includes:
- Be everywhere — Don’t just stick to LinkedIn and Indeed. Explore niche platforms, industry-specific job boards, and professional communities.
- Prioritize conversations over applications — Focus on meeting 2–3 new professionals each week, without immediately asking for favors.
- Use AI as a support tool — Leverage platforms like Ramped Autopilot to automate tedious job search tasks, tailor resumes faster, and focus your energy on real human interactions.
There is no shortcut to standing out — but the right strategies will dramatically shorten your search.
Final Takeaways: Play the Long Game
Tobi’s journey shows that the fastest path to success is rarely the straightest. It's about consistently aligning small moves with your larger life goals. It's about playing the long game — thoughtfully, patiently, but relentlessly.
Whether you’re making your first career pivot, considering entrepreneurship, or just looking for more meaning in your 9–5, the key is clarity. Clarity about where you’re going. Clarity about why it matters. Clarity about what truly fulfills you — not what looks good on LinkedIn.
If you want support creating a smarter job search strategy in 2025, join us inside Ramped Autopilot — and don’t forget to use promo code GETTHATJOB100 for an exclusive $100 discount.
The career and life you want won't happen by accident. It's time to build it — one intentional step at a time.
Things You Need While Searching for a Job
Once you are armed with the knowledge about what kind of job will make you happy, there are core things to get lined up for a job search. Let's look at a few.
№
Name
1 Value
2 Value
3 Value
4 Value
5 Value
What to Look for in a Job
Fun fact, most people will have about 12 different jobs in their working lifetime. This goes to show that finding a job that you love enough to hang onto takes some forethought and possibly a bit of trial and error. Just the same, you can make some plans in advance, helping you land in a position that leaves you perfectly content. Check out a few things to look for when looking for that perfect job.
