In a recent LinkedIn post, Ani Filipova shares two significant personal decisions that, while seemingly risky at the time, ultimately reshaped her life and career trajectory. She frames these choices not as conventional gambles, but as pivotal moments that offered profound rewards and a narrative worth recounting.
Filipova recounts her first major risk: taking out a mortgage at the young age of 25 to purchase a small apartment. This decision left her with very little disposable income, a move that many around her viewed as unwise. However, a subsequent economic downturn in Bulgaria led to the devaluation of the national currency, the lev. This unexpected turn of events significantly reduced the real value of her loan repayments, allowing her to pay off the mortgage faster and subsequently qualify for larger loans to acquire more substantial properties.
“That first terrifying step changed my entire financial trajectory. If I hadn’t taken it, I wouldn’t be living where I am today.”
The Financial Foundation Built on Early Risk
Filipova highlights how this initial, nerve-wracking financial commitment laid the groundwork for her subsequent financial growth. As she notes, the perceived risk was mitigated by unforeseen economic shifts, underscoring how external factors can influence the outcome of bold personal decisions. This experience, she suggests, taught her a valuable lesson about the potential for seemingly precarious steps to lead to substantial long-term gains.
Walking Away from a Prestigious Career
The second, perhaps even bolder, risk Filipova details is her decision to leave her position as COO at Citi after 21 years. This was a career many would aspire to, representing a significant level of achievement and security. However, Filipova explains that remaining in that role would have meant forfeiting opportunities that have since defined her current path.
“After 21 years. After making COO. After building a career most people dream about. I left.”
According to Filipova, this departure from a long-established and high-profile career was essential for unlocking new possibilities. She argues that without this leap, she would not have been able to pursue her current ventures, which include hosting a podcast, writing, building a paid community, and launching her Portfolio Career Accelerator.
The Opportunity Cost of Safety
Filipova contrasts the conventional approach to risk assessment, which often focuses on percentages and success rates, with her own experience. She posits that the true measure of risk lies not in its statistical probability of success, but in its potential to fundamentally alter one’s life story.
“We like to talk about risk in percentages. Hit rates. Success rates. Odds. But the exact success rate doesn’t matter. None of the risks ruined my life. These two completely rewrote it.”
In Filipova’s view, playing it safe can often lead to a life devoid of significant growth and compelling experiences. She emphasizes that the rewards of taking calculated risks extend beyond financial or career gains, encompassing personal freedom, time with loved ones, improved well-being, and ultimately, a richer life narrative.
Embracing Risk for a Fuller Life
Filipova concludes her post with a strong encouragement for others to confront their fears and consider the risks they might be talking themselves out of. As she powerfully states:
“Ten years from now, you won’t regret the risks you took. You’ll regret the ones you talked yourself out of.”
Her message is a call to action for accomplished professionals who may feel stagnant despite their successes, urging them to consider building a portfolio career on their own terms. Filipova’s insights underscore the idea that true fulfillment and a life worth telling stories about often lie just beyond the perceived safety of the familiar.
📝 About This Content
This article is based on insights shared by Ani Filipova on LinkedIn.
📅 Originally posted on January 13, 2026 | View original post on LinkedIn →