What I learned from applying to my first job in 8 years

I did not expect to be saying this but… in November 2018 I applied for a job. (wait, what?)

I absolutely love my business and it’s not going anywhere but a job with an irresistible set of characteristics caught my eye and I decided it wasn’t 100% crazy to throw my hat in the ring.

(What in the world could be an irresistible set of characteristics that would have this business owner apply for a job, you say? Customer service - one of my FAVORITE things in this world, getting to support business owners, and something that is both part-time and short-term because I’m not looking for a full-time job)

Despite being a bit of a scary experience (it’s been 8 years since I formally applied for a job!) it was also incredibly empowering implement so much of the wisdom I’ve gained from working with clients over the past few years.

Here are 3 topics I talk to clients about almost every day that I got to experience first-hand as I applied for this job:

1. Get the story clear in your own mind so you can communicate it clearly to others.

So much of job applications and interviewing is storytelling.

When I first saw the job posting, I felt this immediate overwhelming desire to apply and couldn’t fall asleep that night because my brain was on fire with excitement.

If you’re surprised, let me tell you how surprised I was! You can probably imagine the story that was occurring in my head:

  • “Brain, what are you doing?!? Why are you getting so excited about this job?”

  • Why am I having the completely irrational thought of applying for this job? I absolutely LOVE running my own business and it’s going incredibly well!

  • Why would I want to go back to customer service?

  • Why would I want to do something part-time for a few months?

It made no sense at all in my own mind.

However, as I thought about it more over the next couple of days, I came to understand why my intuition had been so spot on and it actually made perfect sense to apply.

Now, when I got to the interview stage, I was effectively asked “umm… we don’t usually get applicants like you, why do you want this job?”

For some of you, that may be your worst nightmare! Having an interviewer ask about the career switch you’ve made or the time gap in your career history is the thing you’re trying to avoid at all costs. For me, I saw it as an inevitable question and used it as an opportunity to tell the story incredibly clearly about why this job is a great fit.

Instead of saying “I know, how weird is it that I’m a career coach applying for a part-time customer service job, it felt so irrational!”, I was able to say “great question, here are the 3 specific reasons why I’d be such a great fit for this job and why I was SO excited to apply…”.

It changed the interviewer’s perspective from confusion to complete understanding - and it landed me the job.

2. Define your non-negotiables so it’s easy to say no to what doesn’t work.

You may remember an earlier blog post about the purpose of interviews and the importance of interviews being a two-way street. Not only are they assessing you for fit, but you should also be assessing them for fit. It’s so easy to get swept up in the game of convincing an interviewer you're a good fit for a job and then totally forget to evaluate if it's actually right for you.

During this application process, one of the questions was whether I was excited to work on weekends.

I understand that working weekends is great for some peoples’ schedules and for me, I have absolutely no desire to work on weekends. None.

I immediately saw that there were two ways I could respond.

  1. I could say whatever I thought I needed to say to land the job (“Yes! I’m ready to work any time you need me!”) and then find myself unhappy in a job where I was expected to work weekends. Or…

  2. I could be very clear about what I was excited about (exceeding customer expectations and working a weekend day here and there if needed, along with a day off during the week) and what didn’t work for me (I know burnout is one of the biggest challenges for customer service folk and I’m committed to having boundaries and recharging on the weekends) and let them choose if it was right to proceed.

It’s lose-lose if I wind up in a job where I’m working weekends and miserable about it. By being clear, candid, and aware of my own needs, I felt good about my answer and was able to help them identify if I was the right fit.

3. Create options for yourself and cultivate multiple opportunities.

After the initial shock wore off of wanting to apply for the job without knowing why, I realized that one of the biggest opportunities for me was to keep up my skills in customer service. I worked in customer service for 6 years before running my business and if I couldn’t have my business for any reason, I would most likely return to customer service as that’s where most of my career capital lies.

For me, this part-time, short term job was the perfect opportunity to keep my options open in a very contained way. I don’t have to close my business and take a full-time job to keep up my skills in customer service. I get to keep my skills active a few days a week while running my business, as a bonus I get to support business owners, and in another few months, I go back to running my business full-time.

I always advocate for clients building a life filled with options and finding ways to prototype anything they’re interested in or want to have as a career.

So if you’re in interview mode…

  1. What are you terrified that an interviewer is going to ask you or notice about your experience? How can you see that as an opportunity to craft an incredibly clear story that actually lands you the opportunity?

  2. What are your non-negotiables? Needing to pick up your kids at a certain time every day? Living in a certain area to be close to the ocean because you’re an avid surfer? Whatever it is for you, be clear about the dealbreakers and don’t get sucked into anything that isn’t a good fit.

  3. How can you keep your eyes open for unexpected opportunities? How can you cultivate multiple opportunities for yourself during this job search? Is this a stepping stone job that gets you closer to your longer-term goals? Are you looking for options that keep up existing skills that you’re not necessarily using at the moment?

Using these three tactics, I was able to experience a job search where I prioritized fit for both me and the company with exciting results.

Now I get to run my business while doing a few months of customer service! I can’t imagine anything better.

P.S. For one additional tip, don’t talk yourself out of an opportunity before you even apply. I had a two-week vacation scheduled which almost stopped me from applying in the first place. In the end, it was absolutely a non-issue, and I almost missed the opportunity because I thought I knew what would be a deal-breaker for them.

What are you choosing to go big on?

One of my absolute favorite books is Essentialism: The Disciplined Pursuit of Less because it is filled with terrifying truths about how much we let other people dictate our time and energy. The author writes that “when we surrender our ability to choose [our priorities], something or someone else will step in to choose for us. […] We can either make the hard choices for ourselves or allow others—whether our colleagues, our boss, or our customers—to decide for us.”

Of course work will choose our priorities if we let it, of course other peoples’ requests will choose our priorities if we let them, of course personal life responsibilities will choose our priorities if we let them.

So the challenge is to start being intentional about what we say yes to and what we prioritize.


One of my favorite topics in the book is the idea of “No “yes.” Either “HELL YEAH!” or “no.”” by Derek Sivers. “The key is to put the decision to an extreme test: if we feel total and utter conviction to do something, then we say yes, Derek-style. Anything less gets a thumbs down.” What would things look like for you if you only said yes to HELL YEAH things? The book argues that instead of asking “what do you have to give up?” it allows you to ask “what do I want to go big on?”

I was sharing this book with a client and after she identified that she wants to feel more intentional with her time, I challenged her to make a list of things she’s choosing to de-prioritize. As often happens, as I made the suggestion to the client, I thought, I want to make a list for myself and really take a look at what I’m prioritizing.

Identifying what you want to go big on

Here’s the very simple activity I did in case you want to follow along (and feel free to use the framework I put together here!):

  1. I identified all the activities I’ve done in the past few months and made a big list from both work and personal life - chorus rehearsals, in-person coffees with other business owners, volunteering, hosting events, running workshops, taking part in different business owner communities, etc.

  2. Then I made two columns - “Prioritizing (Going Big On)” and “De-Prioritizing”.

  3. Then I placed all the activities in the column that felt right - I want to go big on my women’s barbershop chorus this year because I’ve been invited to sing with a quartet that will compete next year, I want to go big on two areas of my business (referral partners and consistent writing and sharing my ideas), I want to de-prioritize hosting events and workshops, I want to de-prioritize one of my volunteering commitments, I want to de-prioritize in-person chats while my schedule is a bit busier over the next few months.

  4. And I made an “I don’t know yet” space for activities that I’m not quite sure if I’m choosing to go big on them. I’ll revisit this list and see if I get a clearer answer after the holidays.

Revisit and re-evaluate as needed

It’s interesting that making this list has already prompted a feeling of relief for me. It’s not that I can never prioritize workshops ever again, but actually it does make sense for me to de-prioritize them right at this moment. It’s important to remember that we can always revisit and re-evaluate any decisions we make about how we spend our time and energy.

I also imagine that going forward it will give me a lot more clarity and confidence in my answers to requests and opportunities that come my way. Knowing what my main priorities are for the next few months, I’ll be able to asses whether the requests I receive fit into those priorities and deliver a clear yes or a clear no.

What are you choosing to go big on after the holidays and what can you actively choose to de-prioritize at the moment?

FLOUR + BUTTER: Job or Hobby?

(I make no apologies for the volume of photos of delicious baked goods in this post)

If you ask my neighbors about the best part of living near me, you’ll get the same response - the volume of baked goods that comes from my place.

The most recent birthday cake I made for my husband.

The most recent birthday cake I made for my husband.

I love baking. A lot.

When I was doing my coaching certificate, we had a homework assignment to plan a full day of something we loved and I chose to spend 14 hours making homemade croissants. (I’m also a bit insane.)

I love making birthday cakes, desserts when we have people over for dinner, sourdough bread, fiddly pastries, and everything in between.

To me, baking = engineering.

It’s precise and hands on and requires immense attention to detail. I want to get a list of very specific steps and execute the heck out of it. It is so immensely satisfying.

Napoleon with caramel mousseline (homemade puff pastry). Beautiful to look at, messy to eat.

Napoleon with caramel mousseline (homemade puff pastry). Beautiful to look at, messy to eat.

So naturally, when you have an interest and something that you’re good at, people tell you to do it as a job!

And this story, is exactly why (at least for now) I know that keeping baking as a hobby is the right choice for me.

Mmmm chocolate croissant.

Mmmm chocolate croissant.


In 2016, after baking for fun for many years (and hearing “you should be a baker!” for many years), I decided that to treat myself to a 5 day class at the San Francisco Baking Institute.

(If you have any interest in baking, I recommend you take a class IMMEDIATELY - they have one day courses, weekend courses and 5 day courses and they are phenomenal.)

It’s something I had always wanted to do and after I left Google, I finally had time to do it.

So! I signed up for:

Foundation of the Pastry Line: Focusing on a variety of tart doughs, pate a choux, and pie dough, this class teaches how to create a sensational array of pastries, ranging from rustic to refined, sweet to savory, and simple to complex. Hands-on: Paris Brest, eclairs, caramel chocolate tart, variety of pies and more...

So so so so so happy. Also the lemon meringue tart was delicious.

So so so so so happy. Also the lemon meringue tart was delicious.

I got my baking jacket as instructed (talk about feeling like an imposter!) and jumped into the 5 day course. I was one of the only enthusiast bakers (most class participants are professional bakers and a lot of them fly in from countries all over the world) and my benchmate was a baker who runs several French bakeries in Canada.


I’ve never had more fun in my life.

I baked for 8 hours a day for 5 days straight, my feet have never been so tired in my life, I baked more than I have in the previous 3 years and if I had the chance, I would do it all again the following week.

So wait.

I loved it? It was the best? I wanted to do it all again?

Then why don’t I want to do it as a career?

Bear claw.

Bear claw.


Here are the things I loved about the baking course:

An example of what one day’s agenda looks like and the amount of things we make… and bring home.

An example of what one day’s agenda looks like and the amount of things we make… and bring home.

  1. Learning: I got to learn an unbelievable amount in those 5 days. We had lecture every day to learn about the properties of butter, the differences between active-dry and instant yeast, why you need to boil pastry cream (it’s because of the cornstarch), why you need two different kinds of crusts for the bottom and top layer of an apple pie, etc. As the most curious human being there is, I was FASCINATED.

  2. Variety: We got to make an incredible variety of things, every single day was different. One day we’d make 7 things. The next day we’d make 5 new things.

  3. Challenge/Novelty: I had made almost none of the things we baked across the 5 days. It was all new to me and challenged my brain every single day.


What this class helped me realize is that the things I loved about the 5 day class aren't necessarily the things I would encounter if I did it for a job.

  • I wouldn’t have lecture every day and feel like I was constantly learning

  • There may be some variety, but on the whole I’d probably be making a repetitive collection of pastries

  • The challenge of newness would be gone pretty quickly.

A strawberry and pistachio Breton tart.

A strawberry and pistachio Breton tart.

I learned a few other things that weren’t a good fit for what I know about myself:

  • Bakers work unbelievably hard. Some bakers start work at 3am or earlier. My 5:45am wake-up was rough enough for 5 days, I can’t imagine 3am. Or doing it every week of my life.

  • I know that I enjoy taking my time while baking and I’m not a particularly fast baker. Watching some of the other professional bakers, I saw that volume and output were baked into their actions (pun definitely intended). They were focused on doing things quickly and creating as many of a thing as possible because that’s how they operate in their own bakeries. To me that might take some of the joy out of it.

Getting to meet the founder of the San Francisco Baking Institute, Michel Suas ( swoon)

Getting to meet the founder of the San Francisco Baking Institute, Michel Suas (swoon)

Knowing that working in a bakery wouldn’t prioritize my biggest values or the working environment I need in order to thrive, gives me the confidence to say that working in a bakery is not a good fit for me.

So I’m baker for a week, once a year, and absolutely love that experience.

(Last year I did the course on Viennoiserie and this year I did sourdough. Next year I’ve got my eye on cakes.)


Now. I’m not saying that I won’t ever do baking as a job. My priorities could change, I could start to find joy in getting really good at a small number of pastries, I could do it for a summer to test it out again in the future, etc.

Or, I could design it based on what I know about myself.

How might I design a baking job around what I know I need in a job? Two ideas to show how you might do this:

  1. Knowing that I would never survive a 3am wake-up, what if I opened a bakery that was open just for dessert? Pastries available 8-11pm?

  2. Given that I loved the challenge/learning/novelty aspect of the class, what if I had a pop-up bakery that only made one thing every day and sold out when the pastries were gone? I’d get to choose what I want to make every day and it could be different every day. I could try new things as often as I’d like.

These cinnamon rolls are unbelievable. I wish this could be scratch-n-sniff.

These cinnamon rolls are unbelievable. I wish this could be scratch-n-sniff.

So for anything you have as a hobby and you’d like to know if it would be a good job, I suggest a few things:

  • Test it out in the smallest way possible! Do a one day class, shadow someone who does the job, sign up for a short course. Don’t quit your job and spend all your money on more training before testing it out.

  • Articulate what you loved about it. What was great, which of your values did it prioritize.

  • Compare that to what it would actually be like if you did it as a job. Talk to someone who does it as a profession and check any assumptions you have.

  • See if you can creatively design a way to do it as a job that would be a good fit what you know about yourself. Knowing what you do and don’t like can be very useful as design inputs for how to make the job a good fit for you.


And so I love my hobby.

I’ve been known to bring homemade croissants to my workshops (did I mention you should come to my workshops?)

I’ll continue taking classes at the SFBI as long as I can.

And when people suggest it as a job, I’ll thank them and not feel any pressure to become a baker, because I know that it’s not the right fit for me.

Strawberry cupcakes with strawberry buttercream.

Strawberry cupcakes with strawberry buttercream.

Homemade croissants I brought to a workshop.

Homemade croissants I brought to a workshop.

Pear Bourdaloue Tart.

Pear Bourdaloue Tart.

If you're analytically minded and feeling uninspired or crushed by an ill-fitting job, check out my group program - Crushed to Confident. Get un-crushed, rigorously evaluate and understand your current role and confidently make career decisions that feel good to you. Join the list here to get first access to the 12 spots.

The Terror of Leaving a Seemingly Perfect Job

We're terrified to leave a seemingly perfect job for fear of what other people will think.

“You’re crazy to be giving this up.”

“Why would you ever leave this job, it’s the best there is!”

“People would kill to be at this company.”

I've had so many conversations recently with people who have fancy jobs that look incredible on paper, have a great salary, don't even ask them to work too hard in some cases, and look like success to the outside world... but aren't what the person wants.

Something is missing, whether it's purpose, contribution, flexibility to focus less of their life on work, or something they can't put their finger on yet.

They've all known that it's not the right fit but they worry that they'll appear ungrateful if they leave the job. That they’ll crumble under the backlash they get from other people questioning their decision.

And then the inner voices kick in.

Who am I to leave a job that's so great?

Why can't I just be satisfied in a job that everyone else thinks is awesome?

Do I really think there’s something better out there?

Being able to make a decision that goes against what other people think, and knowing why it’s the right decision for you, is one of the most empowering things you can do.

I think of the book Roadmap and their concept of something they call “The Noise”. They define it as anything that comes at you that doesn’t take your individual personality into account. The advice, pressure, expectations, etc can come from peers, society, family or even self-doubt. Everyone may have the best intentions when giving you advice, but they don’t necessarily know what’s right for you.

I spoke to a woman who experienced the worst time of her life working at Facebook but felt she couldn’t tell her family that she wanted to leave because they were SO proud of her for achieving what looked like the pinnacle to success.

I spoke to a man who worked at a prestigious law firm who was terrified to step away and leave the prestige despite knowing it was a terrible environment that he desperately wanted to escape from.

I am the person who voluntarily left Google and received endless confused stares as to why I would ever leave the number one place in the world to work.

We get trapped in an external version of success and it creates so much dissonance in our lives.

In some ways, the choice is to risk appearing ungrateful and having people judge you or being miserable at a place that doesn’t work for you.

The easiest way to make a decision you feel good about is to know WHY you’re making the decision.

The more clear you are about what’s important to you, what you want out of work, what energizes and drains you, what environment you need in order to thrive, and what your strengths are, the more clearly you’ll be able to articulate that to others.

You’ll know your exact reasons when you’re asked the questions of “why would you ever leave xyz job??” and if you choose to, you can confidently explain why it’s the right decision for you. This value is missing, that strength isn’t being engaged, what’s actually important to me is this, I thrive in this type of environment, etc.

There is courage and leadership and grace in being able to do something that is right for YOU, regardless of what the norm is.

Stepping through the terror and leaving the seemingly perfect job may actually be an inspiration for those around you. We don’t know what kind of external versions of success those around us are trapped in.

So to anyone that feels guilty, ungrateful or crazy for thinking about leaving a seemingly perfect job, I see you as none of those things. I see you as courageous, filled with integrity and on the edge of making one of the most empowering choices of your career.

Thank you for being brave and showing us the way of doing what’s right for you, regardless of what other people think.

If you're analytically minded and feeling uninspired or crushed by an ill-fitting job, check out my group program - Crushed to Confident. Get un-crushed, rigorously evaluate and understand your current role and confidently make career decisions that feel good to you. Join the list here to get first access to the 12 spots.

Careers and Cooking Grease

Several months ago I participated in a fantastic leadership course where I did one of the most confronting yet rewarding tasks in recent memory - make a list of all the areas in my life where I've been "tolerating incompletion" and get them completed.

(If you're cringing right now just reading that suggestion, you know exactly how I felt.)

This could be chores, hobbies, things we told other people we'd do, etc, and from that list, we then had the challenge to complete five of the items by the end of the weekend.

I made a list of 5 things (which was uncomfortably easy to do) by walking around my house and seeing unfinished projects, unused cooking gadgets, household chores and more. Starting the list initially filled me with shame but by the end of the list I was filled with a new sense of freedom and determination. By acknowledging the things that I had been tolerating I could actually choose to do something about them.

But there was one item that I was horrified by how long I had left it incomplete.

The most embarrassing thing that I had been tolerating was... a jar of cooking grease.

Oh cooking grease. (sigh)

I had been meaning to get rid of this jar of used cooking grease for a long time. I'm not actually quite sure how long but I lived in that apartment for 5 years, so no more than that? (That's not really making it sound any better is it.)

People would look at the jar and say, "what is this?" and then be horrified when they picked it up and looked. I would quickly try to distract them and make them forget they'd ever seen that on my kitchen counter.

Now, some context, I used to work as a recycled water engineer and I know exactly what happens when you put cooking grease down the drain so there was ZERO chance that was going to be the way I dispose of it. But every time I thought about the dang jar of grease I would have the same exact swirl of thoughts - what should I do to dispose of it responsibly, not in the drain, people say not to put it in the trash, even the compost isn't the right place for more than a few tablespoons, I think there's a place nearby that recycles it but I don't really know...

And then MEH. My brain would overheat, I would get overwhelmed and then completely give up.

And so it sat there for years.

Back to the leadership program, I knew that the jar of grease was getting recycled as if my life depended on it.

And so I did two minutes of research, walked 15 minutes and recycled it properly. 

Uh, I'm sorry, wait what? It took 15 minutes?? That's all??

With the amount of time that the swirl of thoughts went through my head I could have walked there and back 25 times. 15 minutes to solve a problem that had been grating on me for years? I think that's what they refer to when they say "death by a million papercuts".

What got me moving was a kick in the butt from the leadership program, acknowledging the incompletion, accountability from the team and a deadline. It took all that to be kicked out of my kitchen grease stupor. I still shake my head when I think back about the number of years it sat there and how easy it was to complete the task.

Eroding Self-Trust

Why is it so important to do the things we say we want to do?

Because NOT doing them erodes our self-trust and our experience of ourselves.

I first read about the idea of eroding self-trust in the book, "The Speed of Trust". Their example was snoozing the alarm clock every morning. We set our alarms with the clear intention of waking up at a certain time and then we snooze again and again and again, constantly making and breaking our commitments to ourselves.

Two quotes from the book illuminate the importance of self-trust:

  • "When we keep doing this over and over again, we lose trust in our ability to make and keep commitments and we fail to project the personal strength of character that inspires trust."

  • "The more experience I've had, both personally and professionally, the more convinced I have become of the importance of making and keeping commitments to ourselves. Every time we make and keep a commitment to ourselves we increase our self-confidence. We build our reserves. We enlarge our capacity to make and keep greater commitments both to ourselves and others."

So the bad news might be that it's easy to make a list of all the areas where you're tolerating incompletion but the great news is that keeping a commitment to yourself and taking action can rebuild that confidence and your capacity to make commitments to yourself.

Tolerating Incompletion: Round 2!

Because this was one of my favorite experiences from the leadership course, I recently did this exercise with the participants of my group program, Crushed to Confident.

I wanted to do the exercise with them so I came up with another list of about 14 things I was tolerating in about as many minutes. Half of them came to me off the top of my head, the other half I walked around my house and had visual reminders of all sorts of things.

You can get a glimpse of all my weird and wonderful hobbies :D

You can get a glimpse of all my weird and wonderful hobbies :D

It was exciting and vulnerable to share with the participants how long some of these things had been on the list. 

Then I had them share with each other - where have you been tolerating incompletion in your work or your life? 

The answers were so normal and universal that it was almost comical: needing to get rid of old furniture that had been sitting there for years, getting in contact with a gardener, putting things on the walls, etc. The participants had the same experience I did, it was weirdly liberating to declare the things you'd been putting off.

And so we challenged each other to act on 3 things by the end of the weekend and there were some great successes. Dressers mounted to the wall so that kids were safe! Gardeners contacted! Books read! Old furniture removed!

And I was reminded of one of the things that struck me about my first experience - so often the task takes MINUTES compared to the YEARS I've been putting it off. Cleaning my makeup brushes, getting in touch with friends to organize seeing Celine Dion in Vegas, handwashing a piece of clothing, washing the kitchen windows, etc. Was it really necessary to spend so much time avoiding it?

A challenge :D

So! Of course I'm going to challenge you to do the same scary and freeing exercise if you choose.

Here are some places to look:

- walk around your house and look for visual indicators
- emails you always snooze
- people you told you would do something
- hobbies!
- open tabs that you've been meaning to watch/read/etc
- ask your friends (or your partner) what you've been talking about doing forever

And then set yourself a deadline. Even better, get friends to do it with you. Declare some accountability to the internet. Whatever it takes.

With each action you'll restore your self-trust and commitment to yourself.

And hopefully you'll have less [insert weird items such as a jars of cooking grease] weighing on your soul.

Careers and Cooking Grease 

Now. One last note.

If there anything is on your list about work (especially if your friends call you out for saying you're going to do something about your work situation for forever!), check out my group program, Crushed to Confident.

It's returning in October and there will only be 12 spots available. It will not only give you a huge boost of confidence, motivation and direction in your career, but will also get you moving on some of your personal action items as well.

Please don't let the jar of cooking grease be your career. (That is the one of the weirdest sentences I've ever written)

Don't let it sit there for 5 years, grating on you while people ask you uncomfortable questions about it, while the swirl of thoughts runs around and around and around in your head. I just can't stand for that.

I'm committed to you taking action, relieving your crushed self and having a very hard time thinking of where you're tolerating incompletion in your life.

The Relationship Between Risk and Entrepreneurship

A few weeks ago my husband and I had dinner with another couple and the conversation turned to risk tolerance.

Our friends said they're solidly in the risk-averse category and my husband and I agreed that we are too - we're savers, we're not incredibly spontaneous and we love a good plan. 

It took our friend a minute, but it was clear that our answer wasn't fully computing. He looked at me and said "but clearly you're a risk-taker because you started your own business".

This was a really interesting point and I had to think about it for a minute.

The first answer that popped into my head was "it didn't feel like a risk".

As I thought about it more, it really didn't feel like I was taking a risk. I had run the business on the side for a year or so and I had become so unsatisfied with my 9-5 job that there was no way that I could stay, it wasn't even an option. So after having tested it out for a year, enjoying the experience and seeing that I was providing value, the next logical step for me was to move it into a full-time business.

Fast forward to now, I'm reading Originals: How Non-Conformists Move the World and I read the following quotes about the relationship between risk and entrepreneurship:

  • “We find that entrepreneurs are significantly more risk-averse than the general population”

  • "Entrepreneurs who kept their day jobs had 33 percent lower odds of failure than those who quit. If you’re risk averse and have some doubts about the feasibility of your ideas, it’s likely that your business will be built to last. If you’re a freewheeling gambler, your startup is far more fragile."

  • "By covering our bases financially, we escape the pressure to publish half-baked books, sell shoddy art, or launch untested businesses."

This was fascinating to me as I've never concretely thought about the potential upsides of being risk-averse in the context of starting a business.

I read on and found this quote from one of the founders of Warby Parker and was amazed that it was so similar to my own response to my friend's question:

“By the time we were ready to launch, and I had to make the decision this was something we were ready to do full time, it didn’t seem risky. It didn’t feel like I was taking a big leap of faith.”

I share this with you because I don't think this is a message we hear about entrepreneurship and starting a business.

I don't want anyone to be held back by the idea that they're risk-averse and therefore can't be an entrepreneur.

I don't want anyone to feel the pressure of needing to quit their job and do their passion instead of testing out their idea as a side-business.

Bottom line, if you have dreams of starting your own thing and are risk-averse, you're in luck. You may just be able to leverage it to help you build a fantastic business that lasts.

If you're analytically minded and feeling uninspired or crushed by an ill-fitting job, check out my group program - Crushed to Confident. Get un-crushed, rigorously evaluate and understand your current role and confidently make career decisions that feel good to you. Join the list here to get first access to the 12 spots.

5 Ways To Support Someone Who Is Crushed By Their Job

When you’re crushed by an ill-fitting job, it can be hard to talk to your friends for fear of burdening them with your career problems.

But today, I actually want to talk to the people who know someone who is crushed and are watching the struggle without knowing how to support the person they care about. That can also be a really tough position to find yourself in.

What can you do to support someone who is crushed by their job?

What can you do to support someone who is crushed by their job?

Your friend/family member/colleague is clearly struggling. They don’t want to burden you with their challenge and yet you would do absolutely anything to support them. The question is what can you do?

I want to help relieve you of your feelings of helplessness with a couple resources and steps you can take:

  1. READING: I’ve put together a list of my favorite books that have changed the way I think about careers. There are books that help reset expectations about the pressures we put on our job, give reminders that almost no one has a grand plan for their career, reframe dysfunctional beliefs about your career and design a really structured job search of today.

  2. EXERCISES: If they prefer a hands-on approach, I put together a series of exercises here with the spreadsheet genius of the guys at UltraWorking. These exercises can help them learn about their values, assess their current role and make changes and know what working conditions they need in order to thrive.

  3. TALKING: The Muse is a fantastic career resource in general, and I love that they have career coaches you can consult with on a variety of topics. So, if your friend is struggling with job search strategy or they’re stuck in a rut or they just want to do a 30-minute career Q&A, you could connect them with someone who can help.

  4. COUNSELOR SUPPORT: I also want to mention an incredible resource for anyone dealing with workplace issues that would benefit from speaking with a trained counselor. Empower Work is a free, anonymous, and immediate text chat line for workplace issues. It was born from the belief that every person should have an advocate to support their professional journey and equip them with the skills to successfully handle complex work challenges.

  5. GROUP SUPPORT: If the person is analytically minded and crushed by an ill-fitting job, my newest group program pilot is launching in August 2018 and I would love to give them the support of a group. The program, Crushed to Confident, is designed to get you un-crushed, help you rigorously evaluate and understand your current job, and confidently make decisions that feel good to you. Send them the link to the list here to be the first to know more about the program when it opens, we start in August and there are only 10 spots.

Please let me know if there are other resources you recommend for supporting someone who is crushed by their job!

The Miracle Question and The Evidence Question

I recently read a fantastic book, Switch: How to Change Things When Change is Hard, and I was really struck by an interesting framework they shared that is used by Solutions-Focused Therapists. They use the Miracle Question and the Evidence Question to help patients resolve a particular problem they’re experiencing.

The therapist first poses The Miracle Question:

"Something must have happened! I look different!"

"Something must have happened! I look different!"

“Suppose that you go to bed tonight and sleep well. Sometime, in the middle of the night, while you are sleeping, a miracle happens and all the troubles that brought you here are resolved. When you wake up in the morning, what’s the first small sign you’d see that would make you think, ‘Well, something must have happened—the problem is gone!’?”

The book points out that the question “doesn’t ask you to describe the miracle itself but to identify the tangible signs that the miracle happened.”

I started thinking about this in the context of being crushed by your job.

What would the first small sign be for you that you were no longer crushed by your job?

Would it be something that happens right when you wake up? Would it be noticeable at work? Would it be something in your personal life that has nothing to do with work?

I could imagine it being something completely different for different people:

  • Waking up before your alarm

  • Spending quality time with friends/family/your partner and having 0% of the conversation be about your job

  • Having the energy to exercise or do hobbies when you get home

  • Staying late at work because you’re excited about what you’re up to

  • Inspired to pick up some old interests you’ve neglected

  • A colleague praises you on your work or you’re nominated for an award

The question that comes after that is the Evidence Question:

"When was the last time you saw a little bit of the miracle, even just for a short time?"

Thinking back on my own personal experience, the tiniest glimpse that a miracle had occurred in my life had everything to do with my energy.

At the height of my unhappiness at work, I was extremely conservative with my time and resources because I had such low energy. I would need to spend at least 3 or 4 weeknights recharging solo at home so I wasn’t exhausted the rest of the time.

So the first sign of the miracle for me was that I was happy to spend all 5 weeknights doing activities — seeing friends, going to events, participating in a choir, etc. My own happiness at work really allowed me to have the energy to spend time with loved ones and pursue hobbies. I felt a return of my generosity with my time and energy instead of stinginess.

When was the last time you saw the tiniest glimpse of your own miracle? What was happening at that time? What tiny tweaks can you try to get back to that feeling?

If you're analytically minded and feeling uninspired or crushed by an ill-fitting job, check out my group program - Crushed to Confident. Get un-crushed, rigorously evaluate and understand your current role and confidently make career decisions that feel good to you. Join the list here to get first access to the 12 spots.

It's OK to Have a Boring Job.

It’s OK to have a boring job.

(Am I even allowed to say that?)

I don’t think anyone ever tells us that it’s OK to have a boring job. It definitely doesn’t work for everyone. And it definitely does work for some people.

I only just recently noticed how revolutionary this message seems to be. I’ve been sharing it more and more often, the most recent time was at a workshop I co-hosted a few weeks ago. Participants kept coming up to me afterward saying how grateful they were to hear someone say that it was OK to have a boring job.

So now I’m on a mission to tell people that it’s OK to have a boring job if it works for them.


The “Good Enough Job”

Here’s a common experience for a lot of clients I work with: there’s someone in their life that is encouraging them to change jobs because the job isn’t fulfilling or challenging them. Or the client is feeling pressure from the expectations we put on our jobs to be fulfilling, challenging, well-paid, exciting, impactful, fun, inspiring, mission-driven… and the list goes on.

I uncovered the idea of a “Good Enough Job” a few years ago, reading Refuse to Choose by Barbara Sher. She describes the “Good Enough Job” as:

"If a job isn't unpleasant, doesn't eat up more than 40 hours a week, pays well, and provides security - it can give you the freedom to do all the things you love on your own time. People complain about unfulfilling jobs until they understand what the Good Enough Job actually is, and then they feel very different about them.

Think of it as a job that doesn't bother you, whose only crime is that it's just not enough to fulfill your life. But it provides money and security and the freedom to fulfill your life in your free hours. That sounds like a great job to me."

When I share this definition with my clients, one of two responses occur. One is incredible relief that their job doesn’t have to be everything to them and the other is that actually, that doesn’t really work for them because that’s a lot of hours to be spending on something they’re not really excited about.

For the latter group of people, that’s a great thing to know about yourself. Your work is going to be one of the main sources of passion, drive and purpose in your life and you should look for that.

For the former people, that’s also a great thing to know about yourself and you get to stay in your “Good Enough Job” without feeling the pressure of society or friends and family to make a move. As long as you’re getting to choose the tradeoffs and know why it works for you, that’s a great outcome.

One client recently discovered that, for her, a boring job is OK, and it doesn’t mean she's a slacker or unambitious. It really allows her to spend time with her niece which is one of the most important parts of her life right now.

There can be hidden upsides to a boring job.

Your job glass is half full?

Your job glass is half full?

I’ve had clients discover so many upsides of a boring job because it left them with a surplus of time or mental energy.

One client used his boring job to write a novel. He was responsible for tracking his own output and results and he found that he could get all the work he needed to get done in less than an eight-hour day. The rest of the day he worked on writing the novel he’s always wanted to write.

Another client used her boring job to dedicate time and energy to her love of languages. She was able to clock out at a reasonable time every day and head to Russian class.

Yet another client dedicated her extra time and energy to volunteering for a crisis hotline. She was considering grief counseling as a future career and wanted to test it out before spending time and money on a degree and a complete career switch.

If it works for you and your life, a boring job can be just what you need.

Your friends and family may not understand.

One of the most interesting calls I’ve ever had with a potential client was with a guy who didn’t actually want my coaching.

He agreed to do an introductory call with me to get his friends and family off his back. They saw his unfilling job and were really pushing him to move to a job that was more fulfilling.

He was perfectly OK with his unfulfilling job because he was excited to launch a new business and his boring job gave him the time and energy to do that.

Your friends and family really may be concerned that you’re not challenging yourself in your job. The way to make a decision separate from their concerns is to be very clear about why your boring job works for you and why you’re choosing it.

You can also re-evaluate at different stages of life. Just because you choose a boring job at this stage of life doesn’t mean that you won’t want to challenge yourself more in your job in the future, or vice versa. Your purpose can come from your family, your work, your hobbies, your or volunteering. and it may change several times over the course of your life.

Do what works for YOU.

My entire message is that you should do what works for YOU. Own that boring job if it works for you. Find a job that fulfills your drive and purpose if that works for you. Move between them as often as it works for you.

"Repeat after me... It's OK for you to have a boring job if it works for you"

"Repeat after me... It's OK for you to have a boring job if it works for you"

A boring job absolutely does not work for everyone and the trick is to figure out if it does work for you. If it’s revolutionary to hear that it’s OK for you to have a boring job, I’ll tell you a few more times so it starts to sink in.

It’s OK for you to have a boring job if it works for you.

It’s OK for you to have a boring job if it works for you.

It’s OK for you to have a boring job if it works for you.

The key is knowing whether it works for you.

If you're analytically minded and feeling uninspired or crushed by an ill-fitting job, check out my group program - Crushed to Confident. Get un-crushed, rigorously evaluate and understand your current role and confidently make career decisions that feel good to you. Join the list here to get first access to the 12 spots.

Believing the lie of "You Just Know"

Recently I read The Art of Work: A Proven Path to Discovering What You Were Meant to Do by Jeff Goines (a fantastic read, highly recommend) and one idea that he reinforces throughout the book is that 'the way to meaningful work doesn’t always look like a carefully crafted plan'. One part of this in particular really stood out to me, what he calls the myth of 'you just know':

For the longest time, I believed a little lie about people who were fulfilling their purpose, and it prevented me from finding my own calling. What was it? One simple phrase: you just know. When we find someone doing what they love for a living, we tell ourselves a story. It’s a nice piece of fiction, a familiar fairy tale, and a downright lie.

[...] This is what we hear from people who are too humble to admit how hard they worked or are uncomfortable with acknowledging how they got lucky. It sounds like how we often describe falling in love. You just know. The problem is that it isn’t true.

They. Just. Knew.

What an effective way for us to separate the people we see fulfilling their purpose from our own chaotic career path and lack of plan. Lucky for us, every person he interviewed who had found their calling said that they had no idea what they were doing. 

There was no plan. But they acted anyway. They didn’t just know. They chose. [...] We rarely hear this side of the story in interviews and documentaries about famous people. Why is this? Maybe because it sells. Because we’d rather believe the fairy tale that says some people are just special. That way, we don’t have any responsibility to act.

I struggle with this same concept when people congratulate me for quitting my job and following my passion. I'm afraid that the soundbite of 'look, you're doing your passion!' dismisses the two years of flailing and desperation and work and classes and everything else that went into making that choice. I don't ever want to give people the impression that I had a grand plan.

To give you a taste of my "grand plan", consider these points:

  • My career path so far has been Recycled Water Engineer in Australia, Technical Support at Google, now Career Coach. (If that isn't an intentional and well plotted out career path, I don't know what is).
  • Many people told me I would be a great coach... and I had no idea what that meant. I had to go take a class to figure out what coaching was in order to know how to respond to their comments that I'd be a good one.
  • I had ZERO plans of running my own business and I failed several of the items on the 'Should You Be Self-Employed' checklist during one of my coaching courses ('Being self-employed is a long-desired dream or vision' and 'Really wants to succeed at being an entrepreneur and has confidence'. Nope and nope).
  • The only reason I started what I like to call my accidental side-business is because someone asked me if I was taking clients yet.
  • I ran my side-business for two years before deciding to take the leap and even at that point my mindset was "I'll see how this goes before I get my next job"

I'm still figuring it out and I'm ok with that. I never "just knew" that this was for me and it may not even be the end. I've still got plenty of time for more unknown careers. 

If you're trying to move towards a fulfilling career, don't let yourself believe the lie that other people have it all figured out. Embrace the chaos and keep making decisions that will reveal new opportunities. And if this is the kind of mindset shift you need, read the rest of The Art of Work.

The 2-Hour Job Search: Adding Glorious Structure to a Chaotic Process

I love following rules. If there's a systematic and structured way for me to succeed at something, I will follow the rules to a T.

I recently stumbled across 'The 2-Hour Job Search' and I've never been so excited to think about a job search. If I were a job seeker, I would put it into practice immediately. I've never thought about a logical and structured way to approach finding a job - something that I usually see as a mysterious, uncomfortable, and inefficient thing I dread having to do.

To me, here are some of the most interesting points he makes within the first few chapters:

  • Job seekers "equate the feeling of making progress with actually making progress". Eesh, that's a lot of truth time. We always feel better when we submit our resumes to a lot of random online postings... even though we probably won't hear back from any of them. But at least we felt productive! I've never thought about actually prioritizing and being strategic about who I'm contacting and how.
  • You should be making a list of 40 employers to start your search. 40! He wants to make sure people are using creativity at the start of a job search and expanding their thinking past the top 3-5 companies people have in their minds. "I’ve seen this simple act liberate students mentally to the point where they admit their initial career search focus—those first five to ten employers—was more of a family or peer expectation than a personal passion, and they decided to shift their job search focus ahead to that “future” career immediately."
  • We're getting distracted by the big name brands when we should be looking at a much larger section of the population. "99.9 percent of employers have fewer than five hundred employees, yet that other 0.1 percent of employers tends to capture our attention most of the time, making us feel (with the help of often massive advertising budgets) that they are the only options available."

There are specific rules for creating a list of 40 employers, structured ways to assess which of those employers to approach first (based on whether you have a contact there, your own motivation towards the company, whether they're currently hiring, etc), schedules for reaching out and templates on what to say to attract the right people and so much more.

I almost wish I was looking for a job (...said no one ever) so I could try this out. As someone who loves rules and organization and structure, this is my dream. As a career coach, I'll hope to live vicariously through a client who wants to try this out :D

The Purpose of Interviews

I went to a tiny engineering school, Olin College, where part of the interview process is getting invited to 'Candidate's Weekend'. You get to see the campus, do an in-person interview, work with a group of other candidates on a design challenge and generally see what the environment is like.

At the beginning of my interview, my interviewer pointed out that not only is Olin evaluating whether I'm a good fit for them, but that I should be evaluating Olin to see if it's a good fit for me. It was something that they emphasized throughout the weekend and it's still present in their current marketing material:

"The weekends are designed to be fun, informal, and informational experiences. They are an opportunity for you to get to know us, and for us to get to know you."

This idea has stuck with me for 13+ years and I still see every interview as an opportunity for me to evaluate if the place is a good fit for me.

I was reminded of this recently, when 3 clients of mine all mentioned the same thing within about a week - the trap they fall into when they're interviewing for a job.

  1. One client goes on auto-pilot in an interview, turns on the charm, and can convince anyone that he's excited and interested in the position. When he looks back, he realizes that if he had been less salesman-y he probably would have learned more about whether the role was a good fit. His challenge is to not get too excited and immediately decide that a job is the best. 
  2. Another client forgets to evaluate the job he's applying to and falls into playing the game of doing anything and everything to convince someone that he's a good fit.
  3. The third client mentioned tricking the interviewer into thinking he's the best fit but then waking up one day down the line and realizing that it's a terrible fit for what he's looking for. The most appealing thing about any job for him is a change, not necessarily the job itself.

It's so easy for a job to immediately look appealing and to put a positive spin on anything (especially when you really really want a new job). It's harder to step back and use the interview as a time to evaluate your own needs and see how they match. Maybe even see if they can convince you that they're a good fit for what you're looking for.

The really weird visual that popped into my head while chatting to a client about this, was that if you're starving, and someone puts something in front of you that kinda looks like cheese, you'll probably eat it. Too bad that it's actually styrofoam, but you were so hungry that you didn't really take the time to make sure it was cheese. Weird huh. Don't make the same mistake when you're starved for a new job. I want you to have the cheese job and not the styrofoam job.

Is this something that you encounter? Do you get swept up in the game of convincing someone you're a good fit for a job and then totally forget to evaluate if it's right for you? I would love to hear any stories you have about falling into the trap or alternatively, doing an awesome job at using the interview process to evaluate the job/company for your needs.