#16: The Hardest Part of Career Transitions

Major career transitions almost never go smoothly. One of my clients, a strategy consultant, found this out when he switched to self-employment. A year in, he admitted he still wasn’t making enough and was barely getting by on his savings. The constant pressure to secure new clients was intense, causing a lot of anxiety and major self-doubt.

Another client, a driven achiever from the fashion industry, decided to pivot to tech. She dropped $15K on a professional certificate in product management, but even after 1.5 years, she still hadn't landed a proper job in her new field. Frustrated and discouraged, she started to believe she had made the wrong choice and that it was all for nothing.

Everyone knows transitions are hard, and we all think we’re ready for it. But when the going gets tough, many start to question themselves and get overwhelmed with the feeling that they’ve made a mistake.

Why?

The more I talk to people who see their transition as a mistake, the more I realise that by ‘hard,’ we often mean a ‘heroic’ hard—tons of work, problem-solving, new challenges, and pushing ourselves to keep going when we’re tired of difficult tasks.

But there's another kind of hard in career transitions. It’s not about tackling big projects or overcoming obstacles. It's about feeling professionally unwanted and unneeded in your new role, when there is no demand for you, when you feel isolated, when your reinvented new self has not yet found its place in this world. This is when nothing is moving forward. Heroic efforts? Forget it. You need something to work on first—and sometimes, there’s just nothing there.

This is the toughest part. It piles on the self-doubt. Months of downtime, rejections, lower earnings, and feeling vulnerable make us question if we made the right choice. The more success and demand we had before, the harder this new reality hits us.

This doesn’t mean you’re lonely or isolated in life—you might have supportive family and friends around. This feeling relates to your new professional self: you as an independent consultant, you as a product manager, you as a writer, etc.

In sum: When you’re starting a transition, ask yourself if you’re really ready for both kinds of hard. If you are, it won’t hit you as strongly as it could. We only get confused by difficulties when we don’t recognize them as part of the process.?

This is the newsletter series about hidden biases that often cloud our career decisions. We’ll break down the 30 most important ones I've seen in my practice over the last decade, the ones people often say, 'I wish someone had told me about this earlier!'?

I’d love to hear your thoughts! Did this resonate with you or remind you of an experience you’ve had? Please share your insights and stories!