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.

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, I'm running my first group program pilot in August 2018 - 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 be the first to know more about the program when it opens as there are only 10 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, I'm running my first group program pilot in August 2018 - 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 be the first to know more about the program when it opens as there are only 10 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.