The Career Trap of ‘Should’: Ani Filipova on Redefining Professional Goals

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Ani Filipova

LinkedIn Author

I help professionals build career options • Brand building, AI, corporate-to-entrepreneur transitions • AI Advisor • Speaker • Founder Membership community and Accelerator • Ex-COO Citi

In a recent LinkedIn post, Ani Filipova delves into a common career pitfall, identifying the word “should” as a potentially dangerous influence on professional decision-making. Filipova argues that while many career choices are framed by societal or personal expectations of what one “should” do, the critical step is to regularly question whether these paths still align with individual desires.

Filipova highlights the challenge many professionals face in discerning their personal wants from external pressures. She writes:

“You become very good at knowing what the organisation needs from you. What your team needs. What your family expects. What the sensible career move should be.”

This constant focus on external demands, Filipova suggests, can lead to a disconnect from one’s own aspirations, especially after years of career progression. The post emphasizes that the difficulty in answering the question “What do I really want?” stems from this ingrained habit of prioritizing external needs.

Questioning the “Shoulds” in Career Progression

Filipova shares a personal reflection on reaching a point where continuing in the same vein felt unsustainable, despite not wanting to discard years of experience. This realization prompted a shift in perspective, leading her to seek ways to leverage her expertise differently.

The author explains her own transition:

“I wanted to use my experience differently. So I could create an environment where I have: – More freedom. – More variety. – More ownership over my time. – More choice over the work I said yes to.”

This re-evaluation, according to Filipova, opened up previously unconsidered career avenues. She advocates for a proactive approach to career planning, encouraging individuals to move beyond automatic assumptions about the next promotion or role.

Reframing Future Career Aspirations

Filipova proposes a powerful alternative to the “should” mindset: asking a more direct question about future desires. She advises professionals to consider:

The Importance of Self-Reflection

According to Ani Filipova, the crucial question to ask is not about what one is expected to do next, but rather, “What do I actually want the next few years to look like?” This introspective query is presented as essential for ensuring that future career moves lead to genuine fulfillment rather than merely replicating existing circumstances in a new guise. Filipova warns that without this clarity, individuals risk creating “another version of the career you already have.”

To support professionals in this process, Filipova mentions her upcoming Portfolio Career Accelerator program, designed to help individuals identify and shape career options that offer greater autonomy and choice. The program, starting September 28, aims to guide participants in positioning their accumulated experience to achieve a more flexible and fulfilling professional life.

Filipova concludes by urging readers to get clear on their personal vision before making their next significant career move, emphasizing that this self-awareness is the key to unlocking a career that truly aligns with individual wants and needs.

📝 About This Content

This article is based on insights shared by Ani Filipova on LinkedIn.

📅 Originally posted on September 5, 2026 | View original post on LinkedIn →