Career Reflections at 35

Today is my 35th birthday. It also marks exactly 3 ½ years I’ve been running this business, Pivot Journeys. I’ve spent a lot of time over the last few months thinking about all I’ve seen and learned being a coach, and I thought I’d share some thoughts and reflections about navigating careers from the last few years.

1. Everyone thinks they don’t have it Figured Out

I think this may be the most clear realization I’ve had through my one-on-one coaching work: 99.99% of people feel uneasy about their career and anxious about the future. Most people are worried about living their ‘best life’, fulfilling their purpose, or whether they’re making the right career decisions.

When I start working with someone, I’ll get on the phone for an initial 30-40 minute call to see what their pain points are and how I might be able to support them. Ahead of time, I’ll look at their resume or LinkedIn profile and so often find myself thinking, ‘Wow – this person looks so accomplished, on a clear trajectory, and all put together. What could they possibly need me for?’

And then we talk and I hear they’re miserable at work, or bored by their day-to-day, or had always wanted to be in a different field. The outside image people project is not what’s going on in the inside most of the time.

In some ways this is sad to me. But in other ways, it can be really freeing to realize that everyone is just trying to figure out where they fit in the moment at each step of the way. There’s nothing wrong with you if you’re still working on finding something more meaningful or fulfilling – pretty much everyone is.

2. School Is Viewed as An Acceptable Way to Explore

In this quest to ‘figure it out’ there’s this pressure to make it seem on the outside like you have it all sorted. And when people are unsure of their next steps, they often think of returning to school. And somehow this, consciously or unconsciously, excuses to themselves and to others that they’re uncertain of what’s next.

I think this is so interesting… and crazy. Why is it that we as individuals feel the need to go back to school when we feel a bit lost or stuck? Returning to school is like a socially acceptable and recognized way of saying you’re a bit confused and exploring your options. But why can’t we all just explore throughout EVERY stage of our careers and lives regardless of where we currently are?

There’s really no guarantee that school helps us find our way – and if anything, it puts us into a mode of researching, talking, and listening inside a classroom bubble instead of actually trying and doing things. Capstone projects are so popular in programs because they give hands-on experience to apply classroom learnings to the real world. But why should we have to pay tens of thousands of dollars to try things out and build on our skills?

This is why the design thinking framework applied to your life and career was a life changing framework for me, and I’ve incorporated it into most every part of my coaching work. Thankfully, it’s gaining traction as a globally recognized approach to making life and career decisions.

3. Short Term Vs. Long Term Goals Get Crossed

What’s even more perplexing about the push to go back to school is that I see so many people think that more education will help them get to the next stage in their career – even when they don’t know what that next stage might look like.

In general, people go back and forth between short-term and long-term goals. I see a lot of people focus on their immediate next job without taking time to think through where that would put them in 3-5 years. Conversely, many people can see what they want 10 years from now but have a hard time seeing what that means they should do in the next 2-3 years to set themselves up for that longer vision.

Reconciling and blending short-term vs. long-term goals and priorities is challenging for people, and yet there’s got to be a good balance of considering both of them at all times. Again, this is where the design thinking framework seems to help.

4. Self-Awareness Has Nothing to do with Age & We All Can Have More

One of the clearest findings I’ve had is that everyone thinks they’re more self-aware than they actually are, and age has nothing to do with it. I’ve worked with so many people over 50 who don’t realize how they show up to other people. Many times they don’t see their unique, often challenging habits, and personality traits that affect not just their ability to get jobs but also their ability to succeed in their roles.

With over 150 1:1 clients I’ve worked with, I’ve found it’s actually younger people that are more open to self-reflection, and who have a greater and more accurate sense of self.

Every time I do a workshop with a self-awareness tool or deep reflection, I’m know people walk out seeing themselves a little differently or uncovering something new about themselves. Even people who think they’re very self-aware have so much more they can learn about themselves to be more effective professionals and be happier in their careers.

5. Great Work Places Are Hard To Find

I wish this one wasn’t true, but it is. Great workplaces and great bosses are really hard to find. People leave jobs for many reasons – but from what I’ve seen, 99.99% of the time it’s the boss or the culture that drives people away. Harmful leaders are everywhere. We have so much more that needs to be done to create workplaces that are inclusive, fair, values-based, strengths-based, engagement-focused, kind, developmental, and impactful.

6. People Don’t Care About Salary As Much As You Think

There’s a lot of recent research and data showing that most workers care more about career growth opportunities, vacation time, flexibility, and a good benefits package than an extra $5,000 in salary. I witness this every day.

The number of people I work with who are exhausted and frustrated by their 45+ minute daily commute has only increased. (NYC is losing talent because of the subway system that has pushed people to not even consider jobs that are too far from their home.) The number of people who are struggling to balance daycare pick up, with work days that don’t shut off at 6pm is only growing.

I’ve found myself learning of pregnancies before friends and family because people women are worried about how they’ll handle going for a new job, or taking a promotion because they’re about to embark on this new life chapter. Most people would gladly trade an extra few thousand dollars for other benefits. They want more time with their families. More flexibility to go to a doctors appointment. More resources to go to a conference to learn something new. More opportunities to work on new projects that give them new skills. And they want a benefits package that shows the company truly cares about their health and wellbeing.

If companies aren’t willing to change and prioritize what workers want, they will continue to lose the best talent.

7. The Word ‘Culture’ Leads Us Astray

The word ‘culture’ isn’t helpful when picking roles and teams that are good fits. Every person has different needs – what they need and want in a boss, peers, and a team.

Culture is not the foosball table, beer on tap, or weekly bagel breakfasts. It’s how conflict is handled. It’s how people prepare for meetings. It’s what priorities are chosen when time is limited and resources are scarce. It’s how people are held accountable when something goes wrong. It’s how people are kept informed of changes and deliverables.

We all have different strengths and ways of working. As such, we each need a little something different with respect to ‘culture.’ This isn’t to say that a horrible workplace is going work for some people - probably everyone will be miserable, but for different reasons.

I see too many people ignore red flags, not ask deep enough questions, or focus on the wrong things when going through an interview process or accepting a job. The most successful people I’ve worked with go back to ask additional questions after getting a job offer. They probe deeper, talk to more people on the team, and ask hard questions before accepting the job. They are able to confirm it’s the right fit for them, and go in eyes wide open for the challenges they see, and a plan to manage them.

Culture is a dangerous word that means too many things to too many people and we need to do a better job of defining it and creating workplaces that work for individual people.

8. Being Your Own Boss is Amazing…And It’s Also Hard

The first version of Pivot Journeys I started in December 2015 was somewhat different than the version I’m running today. In the first 18 months, I worked through big challenges that eventually took me to a version of my business that I have today – and that really works for me.

I couldn’t be happier to have the business I have now. I honestly can’t imagine going back to a traditional job – the excitement I get from my work (and knowing it’s something I’ve built), the flexibility to prioritize the things in my life that are important to me, and the ability to be in control of my own destiny and learning is life changing. I don’t love every day, but I have bright spots every week - and I am so, so grateful.

Being your own boss is also really hard. Having suffered a lot of health setbacks earlier this year, I felt the effects of not having paid sick leave, and not having a backup coach to take client sessions when I was having a rough week. I beat myself up too much when I’m not hitting the marks I want to hit - way more than if I worked for someone else at another company.

Being your own boss, starting a company, or even just being a freelancer is something that society glorifies right now. Do what you love’ and ‘create your life’s work’ – two slogans that come from WeWork – make it seem like everyone can find work they love, work that they want to hustle for 24/7, and fulfills their higher calling. I think this is a recipe not just for burnout, but constant disappointment.

Being your own boss may not be what you want (or you may know it might not work for you). Or you might be planning to step out on your own in the near future. Either way, know why you’re interested in doing it, think through where your natural strengths will lead you to succeed in being your own boss, and make plans to manage the challenges that will be unique to you.

Possibly my most fun takeaway of the last few years is learning about a ton of different kinds of jobs and industries through my clients - fashion, government, healthcare, construction, agriculture, marketing, law, finance, publishing, philanthropy, consumer research, consulting, entertainment, real estate, transportation, nonprofit, and so much more. There are so many options out there for all of us to create meaningful, fulfilling lives and you never know what you might stumble on next.