Making a Career Transition Solo is a Mistake

sarah caliendo
Jun 8, 2018 · 4 min read

People will change careers several times in their lifetime with the average length they stay at an organization, being only 4 years. So it never surprises me when I’m speaking with several peeps in a given week — all in the thick of their own career transition. There was my friend who’d just been let go from a leadership role. She’d grown the company from the ground up and built her career and her identity there. Needless to say, she was devastated and at a loss for what to do next. She had existential questions, practical fears, and she’d been muscling through it alone.

It brought up painful memories of one of my own career transitions. I appeared successful and driven on the outside, but on the inside I felt like a fumbling hot mess. I’d moved across the country and had offers at startups, but I’d also found out I was pregnant (surprise) and no decision felt even ok. I was scared, overwhelmed and clueless in the wake of big decisions. I had no clarity on what I wanted, so how could I possibly make the right decision?

Time off to think about your next career move shouldn’t be squandered. Whether you’re lucky enough to take a few months off, were fired, or are in a rush to get out of a toxic environment, it’s a key moment to consider exciting possibilities. But I know all too well, how going through it alone can feel confusing, stressful, isolating and well…it’s also inefficient. Here are a few reasons why you shouldn’t transition solo:

You have urgent decisions to make FAST

Whether you have a severance, no savings or you’re weighing offers, you’re facing external pressure and have timelines to uphold. You’d be amazed at how one’s operational prowess and logical thinking, quickly turns into utter chaos in the midst of a major career decision. A coach helps you prioritize and execute what matters against crucial constraints — especially important when you’re getting lost in over-analysis and liable to make fear based decisions. Like in any product development cycle (or business for that matter), circumstances WILL change, and you need to make decisions with agility. A coach adjusts along with you, helping you refocus, holding you accountable to your goals, and pointing out when you’re off track — all critical when time is crucial.

You have no idea what you REALLY want

So many people I work with were very successful in roles they felt they ought to be in, or were great at, but were miserable in — myself included! In my first big career move, it took me nearly a year to even make the decision to leave, and explore other opportunities. Sure, there are tons of lessons that come with mistakes, but who can afford to take months or years to figure out what they’re working towards? And, how can you work towards accomplishing “it”, if you don’t know what “it” is? A coach partners with you to zero in on what you want, why you want it and how this all jives with your values and priorities.

Your network is self-interested and biased

Let’s face it. Your spouse, partner, friends, manager, mentors and recruiters — even though they love, care for and respect you, they all have their own agendas, blind spots and ideal outcomes in mind. Sure, they matter but they can also be limiting and too heavily weighted in your decision making. Also, they know you too well, which is limiting when you’re exploring your next step. A coach provides fresh, unbiased perspective free from personal agenda. A coach’s sole mission is to help you reach YOUR goal. They’re your advocate, they’ll stretch you and they’re unwed to anyone else’s ideals.

You won’t have an edge over competition

There are big misconceptions about coaching, like they’re for executives, or that they’re just for those “on the job”. When you hire a coach — unlike the majority of people in transition, you’re capitalizing on these fallacies. You can take matters into your own hands and hire one not only to make a career decision, but to help you onboard into that new stretch role, or brand new profession. Working with a coach means you have humility, desire for learning and knowledge of your untapped strengths and blinds spots that others do not. This all gives you a leg up.

You’ll be stressed out

According to the American Psychology Association, a whopping 63% of Americans are unable to manage their stress, which is ultimately related to money, career among other things — and we all know how stress leads to poor mental and physical health. I don’t know about you, but when I talk to a thought partner like a friend or therapist about issues in my life, I feel better afterward. Working with a coach feels like that, only on steroids. A worthy coach has several tools in their tool belt that can help you manage your transition stress. Not only are they compassionate listeners, they bring focus, and awareness to what in your transition is stressing you, and help you clearly see how you can take action to reduce or remove it in the future. And, when you’re thinking clearly, more relaxed and feeling confident about your career decisions, you’re happier.

Working with a coach completely transformed my career and my life. I often wonder what I would’ve accomplished (and how quickly) if I’d hired one much earlier. I’ve personally worked with 3 coaches in my lifetime, and I look forward to the next one. If you want to learn more about coaching, say hi at

sarah caliendo

Written by

Bringing humanity into business. Executive Coach. Startup ex pat. Instructor at CycleBar. Creative. Passionate about people.

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