It shouldn’t have been a surprise how similar the journeys of looking for work and love are – both are big commitments that speak to who we are, what we value and where we choose to spend our time and draw purpose. Having done both recently, I’m starting to see some common themes and in many cases, sound advice in one department is sound advice in the other.

1. Online is more Miss than Hit
The Interwebs are alive with sites that claim to be waiting with your match (job or man or woman), if only you go through 3 simple steps:

• Tell them more about yourself (age, height, salary range, current profession, a nice picture of you smiling, but not smiling too much, confident but not cocky, mature but not old, young but not juvenile) – it’s uncanny how at least 50% of the questions you answer for a career profile are the same as a dating profile
• Upgrade to the premium account for 3 months, and if you pay for a year, you get 1 month off! That makes NO sense. Why would it take me a year to find something you claim to already have waiting for me with a nice bow around it
• Relax your constraints – Everything you just told them about yourself and your preferences in step 1 is actually what’s holding you back from happiness. For instance, you told them that you’re only interested in meeting people or finding a job within a 50 mile radius of your current location, but really…what’s in a place. Help them help you by removing these constraints.

You put in all this hard work to help these sites get to know you better, only to be disappointed. The disappointment isn’t just in the inability to find what you’re looking for but the self-worth doubts that start to creep up because of the horrible recommendations these sites give you. My lowest point was when e-Harmony in its infinite wisdom and 20 dimensions of compatibility felt I should go out on a date with a truck driver in Montana. 6 months later (and I’m not making this up), Zip Recruiter suggested that I apply for a truck driver position. After a full-blown existential crisis about why the Universe thinks I should be ‘doing’ truck-driving, I concluded that She has a sense of humor and would like for me to get one as well. Which I did.

As much as I love technology, I don’t think it’s cracked the code for human-networking. Surveys (short or long) are unable to capture the essence of a person and what they want. My most interesting job interviews and dates have been ones where a friend or colleague made the introductions based on his/her understanding of both parties and gut-feel that it might be a good ‘fit’. So what I say to you is: Go forth and meet people! Don’t hide behind that screen and scroll through jobs and humans as if they were products on a shopping website.

2. It’s a numbers game
Whether you go looking online or in the real world, don’t expect your first or second experience of anything to be blissful. That only happens in the movies (or maybe to real people but you can’t really plan for such a serendipitous outcome). The more people you meet and interview (and yes, first dates do feel a little like interviews), the better you understand what you’re looking for. I wrote down what I wanted before I started my quest. 3 months in, 50% of both wish-lists had either been heavily edited or reshuffled. I’m a huge believer in writing things down. It’s a great starting point, but only as long as you don’t get held hostage by your list of theoretical wants. For instance, in my Work wish-list, the nature of the product (i.e. what it is) was at the top – it has to be something I’m passionate about. Yet I’ve realized that day-to-day work life is remarkably similar no matter what the content of the work – the pattern of identifying and solving problems, the human dynamics involved etc. are exactly the same. That’s why over time people/culture have crept to the top of the list. Just as the list informs choices you make, the choices you make and how you feel about them as you live them out must inform the list. With men, I’ve always underplayed the importance of humor in my wish-list (i.e. it’s been towards the bottom of the list) yet it’s one of the first things I notice and one of the most durable qualities I appreciate over the long haul. Surprisingly (for me at least – I’m a libra and therefore prone to vanity), physical appearance  loses it’s shine fairly quickly.

3. Heart or Head, the battle rages on
Time and again, I’ve found myself at a fork in the road where one path represents the thing that would bring immediate relief and joy (e.g. quitting a place of work I detest, picking the emotional wreck of a guy that my friends and family hate and whose unstable mind I’m completely enamored by), and the other path that promises long-term stability and alignment with other life goals (e.g. picking a line of work I am not passionate about but makes good money and lets me buy pretty things and feel safe, picking the boring guy from the ‘good’ family that everyone adores because he’s made of sugar and spice and all things nice).
The mind wants to follow the mind but the heart wants to follow the heart. I’ve tried it both ways and discovered that as long as it’s a choice where one has to be given up in favor of the other, it will not result in durable contentment. You’ll start the journey with a bag of What-ifs. The more arduous the road, the heavier this bag will get. And this will continue until:

• You change course (and if you change it by making a similar decision, you’ll end up right here again) OR
• Try to create your What-ifs in your current life (e.g. Cheating on your partner while still living the doting-spouse life) and cause a cluster-fuck of epic proportions OR
• Die prematurely of a stress-related stroke

Here’s my new-found alternative: Get out of the way and let your heart and your mind talk to each other. They both want good things for you, things that are essential for your well-being. Ask them what they want for you. Visualize what an option that has both sets of things look like. The minute you visualize it, you’ve made it achievable. In time a third path will begin to appear whenever you encounter a decision fork and it will represent the best of your heart and mind’s needs. Eventually the fork will disappear and only one path will remain. The forks in our path are the external manifestation of the fractured existence we live internally. If we can facilitate an ongoing dialogue between all aspects of ourselves, we begin to heal from this fracture. And life starts to become whole.

4. Desperation can be smelt a mile away and it’s not fragrant
Unless you’re in a dire situation (like an impending lay-off or long-term unemployment), the worst time to look for a job or a mate is when you’re desperate to get them to fill a big gaping hole in your emotional life. More so than time, it’s a state of mind. Whether it’s those dying ovaries, or that post-breakup vacant heart that longs to be filled with love, or that raging fear that your bank account is not being replenished fast enough, or that bruised ego that gets battered every day at work by some type-A jerk, the desperation you feel is written on a neon sign above your head. When people see that neon sign, one of two things is likely to happen:

• If they’re self-serving and you have something to offer, they will pursue you as a target for exploitation and play to your desperation. You will lower your bar and make a sub-optimal choice that a more-centered you will regret. To me, everything from excessive low-balling in a job negotiation to manipulative pick-up tricks at a bar represent this mind-set.
• If you have nothing to offer to them and they are the sort that find desperation repulsive (and most people actually do in my opinion –  must be an evolutionary instinct), they will offer attention (because it can provide material for gossip) or pity (often shared in the form of advice) or create distance (since we live in a guilty-by-association world)

So, first rule – don’t start out on your man/job hunt if you’re desperate. Second rule, if you’re feeling desperate, step back and attempt to get back to your center and regain perspective. I find desperation is like an extreme macro lens. Looking through it, your entire vision is the very limited focal span of the lens. All that’s needed is a change in lenses to one that offers a more telephoto view of your life and the world. Here’s a trick that helps zoom out:

• Write down three memories from each year of your life (a few words per memory)
• Then make a list of 10 people you know who live fairly different lives and 3 statements per person about their life story
• Whenever your world starts to become small, read your list. It will give you perspective about your entire life and remind you of good and bad times that have existed before this one particular decision you’re getting desperate about.
• Then read the second list. This will give you perspective that life exists beyond you, in different shapes and sizes from yours but relate-able because you know and care about these people. There isn’t just one path to a destination but many.

If, after doing this once or every day for a while, you begin to feel that you really want what you want but the idea of not getting it does not feel like it will break or you, you’re back to your center and ready to embark.

5. Rejection hurts!
And it hurts bidirectionally (i.e. both rejectors and rejectees experience hurt). However I believe rejection (though inherently painful) doesn’t have to be a soul-crushing experience. What makes it so is two things:

• The meaning we make about ourselves when we don’t get what we want
• The lack of empathy and understanding we exhibit as rejectors and rejectees and the lack of etiquette we use in this transaction.

I believe that both originate from an age-old piece of advice we’ve all been given along the way: Develop a thick skin. Of course! If only your thick skin could prevent you from feeling things, then everything would be peachy! Having tried that for decades (and knowing the soul-numbing effect it has on me), I not only reject this advice but actively work on making my skin thinner. It is precisely when people develop thick skins that they stop relating to their own feelings or the feelings of others and it becomes acceptable to dehumanize themselves and others. A few thin-skinned practices I’ve added to my rejection-repertoire over the years:

• Feel everything! And feel it fully. It’s your emotional compass and there to help you navigate the very murky waters of human relationships
• Never use silence as a way to communicate rejection – talk it through (in-person or written). Explain what was missing for you and why it wasn’t a good fit. Refrain from character analysis. Telling someone they suck is not actionable feedback.
• Never use anger as a way to express resentment or hurt. As a rejectee, it’s so easy to dehumanize the rejector and project arrogance, meanness on to them instead of just acknowledging that it hurts (see item #1 – you’re not really feeling when you’re enacting hatred towards a human dartboard). Look back to the times when you’ve rejected someone or something. Now imagine being forced to accept that person or job instead of having the freedom to reject. Would you wish that on yourself? Then why wish it on someone else?
• As a rejector, put yourself in the shoes of the person you’re rejecting and ask yourself what you’d like to be told that would help you get what you want. You have the unique opportunity to provide critical feedback that could change the course of someone’s life. As an interviewer, I’ve made it an explicit goal to provide feedback at the end of the interview about skill gaps, perception issues etc. Since this is only done with the intention of helping someone succeed regardless of the outcome of the interview, it’s remarkably well-received. I recently ran into someone I had interviewed a long time ago at Microsoft, rejected and had had a lengthy conversation about improvements he could make. He not only recognized me but came up and told me how valuable the feedback was and that he was having a great time at Amazon. It made me happy to know that I had contributed in some very small way to his life, and done so at a moment (i.e. rejection) that is supposed to be painful and to be avoided at all cost.
• Always always always remember that being an interviewer or interviewee, or a rejector and rejectee are just temporary roles. We are NOT the role we happen to be playing. Being human is the only persistent state. So be that – be human and see the human in someone else.

With that, it’s time to get off the soap-box for a month and get out there and experience life. Will report back in May.