Is anyone reading my application?

The way most of us are used to finding a new job is by looking through advertised positions, submitting applications, and then waiting with our fingers crossed. While that’s certainly logical, there are a lot of disadvantages to approaching a career change this way.

When you’re looking to move from one industry to another, or one sector to another, or to shift to a different function than the one you’ve spent decades in, just hitting “submit” on job postings will get you lots of crickets – and frustration at the black hole of application sites.

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If the recipient of your application is a sophisticated online system with algorithms scanning for key words that match the job posting, chances are they only have a superficial understanding of the potential fit (so far, anyway). There’s very little human possibility in this approach, which makes it difficult for an atypical application to get through the filters.

On the human end of things, it can be just as much of a challenge breaking through. Sometimes, the recruiter who is scanning resumes is very black-and-white in their thinking, acting more like the algorithms – how many boxes did this candidate check? – rather than bringing creative, critical thinking to the search.

Other times, the person reading applications is newer to recruiting, or hasn’t really been trained, or wears many different hats – and is going so much on instinct that they might get triggered by a certain university, or reminded of someone they used to work with, rather than making a logical decision on whom to move forward.

For applications that come from career changers, neither the algorithms, nor these kinds of recruiters really know what to do with a resume that is different from what they were expecting, one that raises issues such as:

  • This person is going to want a lot more money than we have.
  • How are they going to fit in to this culture when all they’ve done is ____?
  • This resume is nothing like the others – it doesn’t make sense to me.
  • How does what they’ve been doing relate at all to this job? I don’t see the connection.

Even one of these questions is enough to prompt them to pass on you without getting curious about the possibilities.

Pretty frustrating, isn’t it?

The best way to get your foot in the door to industries you’re interested in, for jobs you might be interested in, is still by connecting with actual people.

In order to do that well, first you need to spend time learning what’s important to you, and what you’re great at – so you can clearly communicate some ideas of where you might fit.

Then, it’s time to build a list of who you can connect with – who in your own network might have ideas, whether for positions that might be a fit, or for people in their networks they can introduce you to. You can certainly use a tool like LinkedIn to help facilitate this process, especially to see who your contacts are connected with, so you can make specific requests of them.

Building your network is your primary tool to make this a much more effective, and lifegiving, process – to remember that it really is about connecting with other humans.

Who are three people you can reach out to this week to move your job search in a new, fresh direction?

Exploring possibilities, not job postings

When most people consider making a career change, they often start by looking at what other job postings are out there, reviewing the lists of qualifications, and seeing if they meet enough of those to apply.

Unfortunately, that’s not a very holistic – or even optimistic – way of going about such a transition.

Comparing yourself to a long list of requirements makes you feel less-than from the beginning. So, you can imagine how that attitude will affect the rest of your job search, and your hopes for finding something better.

The reality is, most companies outline these requirements as a quick way of disqualifying people, because the recruiters on the other end are overwhelmed by applications they often don’t know how to process.

And the reality under that is most organizations over-rely on these sets of qualifications, as if checking all those boxes means they’ll have the right person in front of them. Instead, the process of hiring is really more art than science – sure, there may be some skills or experiences that ARE required to do a certain job. But not 20 of them.


Create Possibilities

When I spend time with my coaching clients to identify their values, their deal-breakers, and their strengths, these pieces start coming together to reveal possibilities for roles and industries that are worth exploring.

For some people, it can feel overwhelming to start from a blank page, so it can help to have ideas to try on, to see if they might fit, or if they bring up other ideas. A career inventory is one way to help you think beyond what you are already familiar with.

The goal at this stage in the process is to find a way – whether through online assessments or by working with a coach – to generate a list of possible ideas. These are potential jobs or career paths that seem to match up with the values you hold, and the strengths and experiences you have. (And at this stage, there’s no such thing as too many possibilities!)


Explore and Research

Once you have this list of possible ideas, it becomes more feasible to begin researching real-life opportunities. You can start by reviewing job postings with similar titles, understanding more about some industries you don’t know as well, and even beginning to do some networking to get a realistic picture of what people in these jobs do all day.

As you do this research, remember it is still exploration – some things will clearly feel they are not the right fit, and that is as valuable to know as what does feel like a fit. Since you’ll be starting with a fairly long list to begin with, the process will lead you to a narrower set of opportunities to pursue.

And, it’s important to remember: don’t disqualify yourself as you go through this exploration. You’re just learning and understanding – and later on, you can get a more grounded sense of how your strengths and skills match up, or what other steps to take before pursuing your longer-term goals.

What are three exciting new avenues you could explore in your career change – even if they seem scary or unknown?

Uncovering your strengths

Once you have a more global view of how you tend to work and see the world, it’s important to get specific about what you are bringing to the table. Rather than approaching this through a resume, I find it more helpful to reflect on questions that will connect the dots beyond what you’ve done in previous jobs, especially if the goal is to make a bigger career shift.

This higher-level process can illuminate some surprising things. Remember to think outside your set of traditional work experience, and include other kinds of work you’ve engaged in – side hustles, early jobs as a teenager, staying home with kids or as a caregiver, volunteer work, community projects, hobbies, and more!

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Be generous with yourself: this part of the process focuses on collecting the dots of your strengths and experiences, and later on, you can work to connect these dots. Use the questions that most resonate with you – we are sparking ideas here, not trying to nail down one life purpose (which doesn’t really exist, anyway!).

  • What are you known for?
  • How do other people describe you, and the role you play on a team?
  • What are you great at?
  • What’s a time you felt most alive in what you were doing? Describe the details of that experience – what you were doing, why, how you were working, with whom… (Now that you’ve thought of one example – what others come to mind?)
  • Where have you felt at your best? (Ideally, where you also felt filled with energy, rather than drained of energy.)
  • What value do you know you have to offer?
  • What do you feel called, or nudged, to do?
  • If you could create your ideal job, what would you be doing? What would your day (or week) look like?
  • What have you learned that you want to apply, or work with?
  • What are some of the common threads that run through the work (of whatever kind) you’ve done – the skills you’ve built, the places that have been a fit, the problems you’ve solved, the people you’ve engaged…?

These can be some heavy questions, and it may seem counterintuitive to a job search not to jump right to resume updates and applications.

Why is it worth taking the time up-front to build some clarity and certainty about your strengths?

It makes your career change or job search that much more effective and efficient:  you will be better able to find roles that match up with how you want to work, and you will be better equipped to communicate clearly in applications and interviews how your strengths will contribute to the goals of the organization.

Plus, you won’t waste your time on opportunities that aren’t actually a match for what you love doing!

Bottom line: This kind of introspection is one of the best ways to set you up as a much stronger candidate, with real clarity on what you want to do.

Finding your center of gravity

Uncovering your values – what matters most to you – is how to start building your roadmap to a career change. And, that list is probably too vague to give you a practical sense of exactly where to go on that map!

The next level of self-reflection is developing more awareness about how you show up in the world and how you engage with others. This kind of information is an important foundation of how you will present yourself in applications – and especially in interviews.

There are a number personality assessments out there which can help you understand your center of gravity in terms of how you work, how you process information, how you work with others, how you stay motivated. They can provide a good place to start – and later, an effective way to know whether the opportunities in front of you will be a good fit. Here are a few of my favorites:

  • Enneagram – a more holistic description of how you approach the world, which can provide some incredible self-understanding (if you’re ready for that kind of work!).
  • DISC – more commonly used in work settings, it helps you understand if you lean toward driving for results, enthusiastically building relationships, providing stability, or conscientiously following process.
  • Four Tendencies – this one zeroes in on how you respond to internal and external expectations, and how those help you get things done (or don’t!).

I like to think of these as helpful information, which might confirm some gut feelings you have – rather than something that scientifically labels who you are for all time. Each of us adapts and evolves with each new environment we work or live in, and we are all capable of broadening our way of being in the world.

Where these kinds of self-assessments come in handy is in reminding you how you tend to operate – and providing you with the opportunity to better explain yourself and what you bring to the table.

A few questions to reflect on:

  • How has it served you to work from this center of gravity? What accomplishments have come about as a result? What are you proud of?
  • How has your center of gravity limited what you could do or accomplish? What examples can you think of where you missed out on an opportunity?
  • How can you use the knowledge of your center of gravity to inform your career move? What past jobs or companies have been a good fit for you, and which ones haven’t been?
  • Knowing what you know now, how can you use your center of gravity in a positive way? What will you do differently in your next job?

What are you willing to shift?

The tricky part about figuring out your values is that you can’t un-know them once you’ve gotten that clarity. Your values will become a north star as you explore opportunities and evaluate them – and, will sometimes feel like a nag.

They will be that voice that says, “I don’t have a good feeling about this,” or “This job is missing a big piece of what you’re looking for.” They might even burst your bubble about a job you were feeling excited about… or make you realize it’s time to move on from the place you’ve been forever.

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The good news is that by leading with your values, it becomes easier and faster to navigate the process of job searching, because you can quickly rule out things that won’t fit.

The bad news is that sometimes it can feel like you’re letting perfectly good opportunities go, and the more time that goes by in your search, the more stressful that can become. And those opportunities might be perfectly good – for someone else.

When you make decisions based on what’s important to you, it means bringing to life a more holistic and inclusive version of yourself, without compromising the essentials.

This isn’t about being an irrational perfectionist, though. It’s unlikely that there’s one job that is 100% perfectly aligned with everything – the right position, the right culture, the right boss, the right salary, the right location, the right office space…

This process does require making some decisions about what elements are NOT a priority for you, or where you are more flexible.

Look at where you can create some wiggle room, so you can get more of what you do want.

  • What are your true needs for salary and benefits? If you are changing industries or sectors, find out how your needs match up with the reality of where you want to be. This is not about compromising on the value that you bring, but about having specific information that will help you know what to expect.
  • What locations are you open to? Especially if you’ve tried for a while to find a job where you are – think about what you love, and what you don’t love about your current location. And do some research on places that might offer more of what you love, and less of what you don’t. (For example – we moved from Boston to Colorado Springs a number of years ago. While I still miss my hometown (and the ocean), living in a smaller city has brought opportunities to plug into the community in ways I never could have back home – and without the traffic I hate!)
  • How might you think about commuting differently? If the best options for positions involve a two-hour round-trip commute in awful traffic, what if you moved closer? There can be some big savings in expenses from thinking like that (here is a blog post that might take you down a rabbit-hole about saving money from commuting).
  • What physical space is important to you? Would you be open to working virtually? From a cubicle? An open office environment?

Understanding your values and your dealbreakers is a key step in your process, and some of these elements will require engaging with your partner or family to explore some of these possibilities together.

The end goal is to have a clear sense of what matters most to you – whether concepts like values or details like desk location – and then you can move through the next steps with the confidence that you’re being thoughtful about finding the fit that is truly the right next step.

Uncovering your priorities

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How do you figure out what matters most to you?

Maybe that question feels intimidating and overwhelming to consider. Sometimes we’ve spent the first half of our career ignoring that question in pursuit of other goals – which is perfectly fine! I think it’s valuable to take time to answer this question, at whatever point in your life it pops up and really demands your attention.

Getting clarity on what you value is a powerful way to help define what might be next for you, or what might need to shift a little in your current set-up. We’ll start there, because often the idea of “finding your purpose” is what’s most overwhelming: as if there’s just one thing you’re meant to do in this life.

My own view on purpose is that it’s more important to have a sense of meaning in what you do, and that definition of meaning can shift over time, and look different from one job to the next, or one phase of life to the next. There are variations of what “purpose” will look like depending on your circumstances at the moment, so don’t stress about finding one particular magical job that is your answer forever.

Here is a simple process to follow to do a deep dive into what matters to you:

Step 1: Reflect on Your Values

Use these questions to prompt your thinking:

  • What are some formative stories from your life that taught you some lessons that still resonate?
  • What are some of the things you want to impart to your kids, nieces and nephews, or other young people in your life? What messages, or what qualities are important for them to know about?
  • What do you think we need more of in the world? What ways of being, what behaviors, what choices would make a difference?

Additionally, you can use lists like this to see what else might resonate with you as priorities in your life – or in your life moving forward.

Step 2: Uncover Your WHYs

Once you have a list of values – whether they’re single words, or stories, or phrases – for each of them, consider why these are important to you. Understanding your WHYs will help with prioritizing – knowing which ones are the most important to you.

Step 3: Prioritize and Analyze

Out of your list, however long it is, identify 3-5 of these values that you want to focus on in this next phase of your life. And then use those to do some introspection on how they match with what you’re currently doing – or to help guide you in making some decisions about where you want to be.

Step 4: Use Values as an Anchor

As you keep these values top of mind, even posted on your wall somewhere, they can be a true anchor to you as you embark upon a shift of any kind – whether changing jobs, pursuing a side passion, or reordering your life priorities. It makes decision-making simpler, if not necessarily easy (there isn’t often an obvious answer, without potential downsides). But the upside is that the decisions you make will feel congruent with who you are and what’s most important to you.


When I interview candidates, I can immediately tell if they’ve done some of this introspection – they are clear about why they’re interested in this particular job, and in that particular organization. They are deeply engaged in the conversation. And they ask thoughtful questions – because they want to do their part to see if there’s a match. They’re not just looking for any job, but the one that will be the right next step for what matters to them.

Why you don’t need a new job

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At a party recently, I found myself in several conversations over the course of the evening about work. In each of these separate discussions, I heard people describing their work with a certain degree of blerg – even for those with new jobs, or those who’ve been quite successful for a while.

We all have to work. We are expected to work, to provide, to contribute.

And yet, more and more people I’m talking to are feeling mildly dissatisfied with how things are. That there’s something missing, and it’s hard to pinpoint exactly what it is. Especially those in or approaching mid-career, in our 40s, are reaching a point of having checked off many accomplishments and benchmarks – titles, certain salaries, teams, projects.

These same people, having achieved things their parents would have been satisfied with, are left wanting more. (But, we don’t want a mid-life crisis…)

Often, that nagging feeling of dissatisfaction translates into saying yes to a headhunter’s call, or scrolling through job postings for one that seems just a little better than the office politics or crazy CEO they have to deal with.

A few months into that new job, after the initial buzz of excitement wears off, the malaise creeps back in. What happened? And why did it come back so quickly?

The problem is – you don’t necessarily need a new job.

The job isn’t always the problem. Instead, it’s about finding more meaning in your work. Looking at what’s underneath all those perks and accomplishments to answer some deeper questions.

Why do you work?

Certainly, there’s a degree of practicality about it – we all need financial resources to live the lives we want. But for you, that’s not quite enough.

And chasing another job isn’t going to fill that hole you feel going to work every day.

You need to go further: What really matters to you? How can you bring that into the work you do (whether the 9-5 part, or outside of that)? How can you create more meaning in how you spend your time? And ideally, also in how you get paid?

These are questions I’ve wrestled with myself in the course of my career – in addition to coaching clients to figure out the right next step for them.

Why does this matter when you could just click the “apply” button on the latest job hunting site?

In my work as a recruiter, I want to hire people who have a hunger to do something bigger with their time and gifts than just check some boxes or find the easy way out.

Because I know those are the people who contribute more and stay longer, who really care about the place and the people they work with.

If you are one of those people – and you want to dive into these deeper questions to find more meaning in your work, schedule your career inventory with me now.

The Value of Clarity

Last year, I finished up a career coaching engagement with a client when we reached the point where he needed to move from thinking about what it would look like to find a career with meaning, to actually landing in a new place – with my support there if he needed it.

Frequently, the work we do together is comprehensive enough to give my clients the clarity they need, and the confidence and support to make that leap. And sometimes, time needs to do its work for a little while longer, for the client to really believe that they can find what they’ve identified – and for the right network or connection to help the opportunity show up.

I sent this client a note to check in, and shortly thereafter got this response:

I landed a management position for an expanding pet supply company… I work 8 min from my house… Most people bring in their dogs so half my time is spent engaging with the animals.

My stress level has been reduced by about 85%, I feel valued and appreciated in my new position, and because they are rapidly expanding there are lots of opportunities for further growth!

Last but not least, I laugh to myself every shift as our location has “giant windows” for the front of the retail suite, and if you recall I said if I were to work inside, big windows were a very big deal to me. Crazy how things work out right?

(A few edits made for brevity and confidentiality.)

Needless to say, I am elated to hear news like this – and I know there’s always some element of faith, believing that my clients will find just the right fit – after we spend the time to construct their personal roadmap.

Why did our coaching work?

  1. He knew he wanted to do something really different than his previous job (owning a stressful business), but didn’t even know what the options could be. Through our work together, we unpacked what he was really great at – customer service, engaging with people, helping to build something.
  2. We also spent time exploring how he wanted to work, not just what he was doing. This anchored for him some key factors like 1) walking his dog during the workday; 2) working outside – or at least in a space with lots of natural light; 3) minimizing stress and taking work home; 4) money and growth opportunities.
  3. We took those strengths and quality of life elements, and identified multiple potential jobs for him to explore – via informational interviewing. Being able to test out potential paths was essential to finding the combination of “what” and “how” – a pet store manager job in a big box store wouldn’t have fit the bill.
  4. We practiced interviewing to build self-confidence. He got tripped up trying to answer standard interview questions because of his unusual background, so we strategized about how to get across what they were really looking for, and how to feel more confident in what he had to offer.

When you have clarity on what you’re great at, what you love to do, and how you want to work, it’s much easier to find the just-right opportunity falling into your lap.

Being open to an unexpected path

My unplanned summer internship turned out to be truly life-changing – in ways I never could have predicted. I found my people. I found the work that made me cry it was so powerfully impactful. I found a level of fulfillment I had dreamed of.

And by the end of the summer, I found the confidence to advocate directly for them to hire me full-time, in DC – because I knew what I brought to the table, and I knew exactly how I could help them in that stage of growth. When I showed up to the small headquarters that fall, I even found the manifestation of what I had imagined my ideal office to look like – down to the mismatched chairs and cramped, collaborative space.

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All the clues I had gathered led me to the place I needed to be.

I stayed with this organization for seven years, trying out several different jobs during that time. It was where I grew up professionally, where my strengths were truly seen, where I was offered opportunities to step into leadership roles and positions I wouldn’t have imagined for myself, but that have put me precisely on the career path that was the right fit for me. (And, I also got to meet my husband!)

The journey that got me to this “right place” took nearly a year, and many applications sent, interviews completed, days of unemployment and dissatisfaction, informational interviews and coffees and emails, and plenty of discouragement and rejection.

These clues added up to something, because I was paying attention.

By going through all of that time and reflection and action and frustration, I gained more and more clarity about what mattered to me, what I was good at – and what I enjoyed doing. When I was offered the internship, there was that voice telling me I shouldn’t walk away from it, even though it wasn’t quite what I wanted. I knew in my bones it was where I needed to be.

This is my own story of finding work with meaning, which was a requirement for me from the beginning. I’ve continued to follow the clues to keep that sense of meaning, which has meant an evolution in my career path over time, as I’ve continued to evaluate how I can best use this sense of purpose and calling to serve others in different ways.

I’m grateful to have participated in the career stories of those I’ve worked with over the past two decades. I know the power of feeling called to be in a new place (as well as the fear that goes along with that), and how you contribute differently when you’re in that place.

My calling now is to be that voice of encouragement, the expert guide along the path to a fulfilling career.

How can I help you follow your clues?

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How to listen for the clues

Getting stuck along my journey of finding a job with meaning was the best thing that could’ve happened to me (in retrospect, of course).

During that time, some guardian angel recommended What Color Is Your Parachute, and another the new-agey yoga retreat center Kripalu. I am eternally grateful I had the opportunity that summer to go to a workshop at Kripalu about life transitions, and to dive into that book – both of which were instrumental in helping me see what really mattered to me, and to envision (in quite a lot of detail) what I wanted to do with my life, who I wanted to be surrounded with, and even what I wanted the office to feel like.

Now, I had lots and lots of clues…

However, these clues didn’t spell out how to actually find the right job – there wasn’t a particular cause I lived for, or a specific role I felt called to do. I didn’t understand it at the time, but I was really a generalist – fairly good at a wide range of things, and especially at bringing different things together. But that made it harder to find anything that felt like a good next step!

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Even though all those exercises and reflection helped me build more confidence and clarity in what mattered to me, it took many more months to effectively narrow my search – and more months after that to actually get the right job.

It wasn’t for lack of trying – and in fact, I think my ability to keep trying was critical to understanding how a search process can work.

But first, I had to deal with applications that went nowhere, interviews that felt awkward, and eventually settling for temp jobs – first, handing out pamphlets at a trade show, and then (at least getting closer) as an administrative assistant for a large nonprofit.

With a secure job finally in place in November, I took a breath, but it wasn’t long before I realized this very old, national nonprofit was way too bureaucratic for me, that my skills weren’t really valued, and that the staff wasn’t treated particularly well. So I went back to my Parachute instructions, and started working my connections for more informational interviews in the nonprofit arena, now having more clarity about the type of organization, or the culture, that would be a better fit for me.

These clues – about where and how I wanted to work – would be game-changers.

The people I met with were genuinely willing to hear about what I was looking for, to share what they knew about the nonprofit sector, and to introduce me to other people they knew – because (I imagine now) they knew that finding great people was a challenge, and they wanted to do what they could to make connections.

It was one of those connections who had a job posting on his desk from an organization that was opening an office in Chicago, and who made an introduction for me. By February, that turned into a job opportunity I was really excited about, and an interview I felt great about… and then, a job that I didn’t get. I was crushed.

I took some time to process and grieve – I had done all the right things! I had clarity on what I wanted and what I was good at, had used all my networking skills (even though I am an introvert and networking is hard!!), and kept meeting with people… and it didn’t work out! And in the meantime, the job that I actually had was getting worse – more mindless, with more turnover in the organization, and a fax machine behind my desk that was straight out of Office Space. I felt stuck. Again.

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A few months later, I got a call from the organization that had rejected me so heartlessly, offering me a summer internship. That almost felt worse… I was now almost a year out of college, and my best prospect was a paid internship, with no clear sense of whether that could turn into an actual job.

But, I had really loved what this organization was doing, how they were approaching the challenge, and the way they welcomed creative thinking and leadership from everyone. The opportunity to do something that better aligned with what mattered to me made it worth the risk. That May, I quit my job and took the internship.

What is a risk – whether small or big – that you could take to move you closer to what you seek?

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