Dr. Gleb Tsipursky – The Office Whisperer
Nirit Cohen – WorkFutures
Angela Howard – Culture Expert
Drew Jones – Design & Innovation
Jonathan Price – CRE & Flex Expert
- Self-sabotage often hides behind logic and fear, quietly blocking promotions and growth.
- Modern workplaces lack mentorship, increasing self-doubt and emotional fragility.
- Building confidence through action and self-recognition is key to overcoming internal roadblocks.
Career obstacles often come dressed as external forces: a toxic manager, poor timing, a slow-moving company, or a lack of opportunity.
But according to career strategist and bestselling author Vicky Oliver, the real threat to growth in today’s workplace often comes from within.
Self-sabotage, she argues, is an overlooked career killer, and one that operates quietly, often disguised as rationality, humility, or even fear of failure. It lurks behind every decision to delay applying for a promotion, defer learning new skills, or stay silent when visibility would help. And in today’s complex hybrid work environment, the internal pressures professionals place on themselves have only become more intense.
Oliver recently joined The Allwork.Space Future of Work Podcast to share insights she’s gained as she’s spent more than two decades studying workplace dynamics, and advised hundreds of professionals — from anxious job seekers to mid-career managers on the cusp of reinvention. Across this range, she sees a recurring pattern of self-doubt paired with inaction.
Imposter Syndrome and the Illusion of Logic
One of the most common forms this takes is imposter syndrome, which is the feeling that despite external success, one is still unqualified, unprepared, or undeserving of advancement. Early in her own advertising career, Oliver experienced this firsthand. She turned down a promotion out of fear, asking instead for “practice assignments” despite having just delivered a highly successful campaign.
“I really put myself back,” she said. “I think it was imposter syndrome.” She hadn’t gone to school for it, and the whole thing seemed beyond her.
What makes self-sabotage difficult to detect is that it often feels like a logical response. It’s easy to justify putting off learning a new technology because timing is inconvenient, or to stay quiet in meetings out of deference to more experienced colleagues.
Over time, though, these decisions form a pattern — one that can stall progress, damage confidence, and reinforce a false sense of inadequacy.
Autonomy, Fragility, and the New Workplace Environment
The problem is magnified by modern workplace conditions. In flatter organizations with fewer formal hierarchies, support systems like mentorship have quietly eroded. Career guidance is no longer baked into company culture. Employees are often expected to onboard themselves, manage their own learning, and navigate office dynamics solo.
“There are no mentors and there’s no mentoring system anymore” Oliver said. “You have to mentor yourself and you have to convince yourself ‘I have to keep learning. I have to keep doing this’ and you will have to tell yourself that, even if nobody else is telling you to do it.”
In theory, this level of autonomy should be empowering. But in practice, it leaves many employees, especially younger ones, feeling adrift. The lack of feedback, coupled with rising performance expectations, can push even high-achievers into a spiral of self-questioning. Oliver sees this play out in the rise of workplace fragility, especially among employees who grew up receiving constant praise and recognition.
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She says that if you’re constantly rewarded just for showing up, it’s confusing when you enter an environment where praise is rare. Confidence has to come from inside you.
In many ways, this internal fortitude is the new essential workplace skill. While technical knowledge can be taught, emotional resilience and adaptability are harder to cultivate. The hybrid workplace only deepens the challenge, creating more room for isolation, ambiguity, and miscommunication — fertile ground for self-sabotage to thrive.
Building Resilience and Taking Ownership of Growth
Rather than wait for external validation or ideal conditions, Oliver urges professionals to adopt proactive habits that build confidence and momentum. This includes carving out time for learning, building a trusted network of advisors, and asking for feedback before formal reviews. These simple steps can protect against stagnation, and give employees more control over their narratives.
Oliver puts this into practice in her own work. Learning new tech systems, she says, is often a source of anxiety — not because of difficulty, but because the timing is always inconvenient. It always comes at the worst moment, so it’s best to prepare before the crisis.
She says the best strategy is to make time for it. Her strategy is to make appointments with herself to stay current, treating upskilling as an unmissable meeting.
Beyond technical know-how, navigating office politics and communication styles is another area where self-awareness can make or break a career. Oliver encourages professionals to study how their managers operate and tailor their style accordingly.
Whether a supervisor prefers weekly check-ins, ad-hoc Zoom calls, or Slack updates, adapting to their preference can smooth friction and increase visibility.
Just as important is recognizing when emotional needs are going unmet. A manager who never gives praise, for example, may not be withholding intentionally — they may simply never have learned how to lead. In such cases, Oliver suggests learning to self-recognize progress.
“You have to pat yourself on the back,” she says. “This is not a false pride…it’s self-protection.”
Still, internal work can only go so far in a system that doesn’t reward it. That’s why timing and company health matter too. Oliver stresses the importance of situational awareness.
Ultimately, self-sabotage doesn’t always look like failure. Sometimes it looks like playing it safe, waiting for perfect conditions, or assuming more preparation is needed before taking a leap. The ability to act, even without full certainty, is what moves careers forward.
You don’t need to be perfect, but you do need to keep learning, keep showing up, and give yourself credit where it’s due, according to Oliver.
