Let me make this declaration before you read any further:

I do not like Valentine’s Day.

How To Suck Less On Valentine's DayAs you might expect, there is a reason why I tend to wear black and shy away from people on the 14th of February every year. The story can be wrapped up to say as a very young woman I was dumped two separate years ON Valentine’s Day BY THE SAME GUY because I was naive enough to give him a second chance.

I’m also the type of person that, in the past, attracted romantic partners that appreciated my extremely “low maintenance” personality. They would express joy on how I didn’t require so much as a card on my birthday because previous girlfriends expected flowers, gifts, jewelry and trips on holidays and milestone events. It seemed to my young self I was being taken for granted because of my un-materialistic heart. For a long time I felt that if I truly deserved flowers, candy and gifts I would receive them and should NEVER have to ask. That would be selfish and self-centered to assume I deserved anything.

Silly me.

As my heart matured and my professional personality started becoming a more dominant force in my life, I started seeing patterns from old beaus to new business relationships.

They both sucked.

Boyfriends that didn’t find it necessary to show appreciation (regardless of the form) where replaced with clients who didn’t find it necessary to show appreciation (regardless of the form.) What does that look like you wonder?

I’m not proud to admit that for a long period of my newly-minted entrepreneurship journey in the early 2000’s I was quite willing to take on clients for greatly reduced (and delayed) fees. Blew your entire $30,000 budget on an “expert,” under a crushing deadline, have nothing to show for it and now your job is on the line? Sure, I’ll help out – I really wanted them to “like” me. The thinking was if I could help you save your job, you’d hire me for what I’m worth later on. I’ll let you guess how that inevitably works out…

Okay, I’ll tell you. The boss was thrilled with the work and rehired the “expert” again because my contact swept me under the rug as he was too afraid to tell his boss he made a bad call in the beginning. There was now zero chance of me ever working for that client again – I use the word “client” loosely because I never did get paid, that would have exposed me as the actual talent. After that there were a few very nice lunches and meetings in fancy conference suites that landed me exactly $0 in new work. And never even so much as a “thank you.”

I was professionally “friendzoned” after delivering the goods. (OUCH.)

For a long time I felt that if I truly deserved to actually be compensated fairly and on time for my work I should NEVER have to ask. That would be selfish and self-centered to assume I deserved anything.

Silly me. Again.

It’s no surprise that over the years I’ve come to be quite an observer of personal relationship and professional networking protocols. Mostly I’m intrigued on how closely the habits, rituals, faux pas and successes of one can be gleaned from to help the other.

So, on this overly retail-heavy guilt-ridden day expressly designed to demand love and appreciation, I share with you my thoughts on how to make your Valentine’s Day suck less – both personally and professionally – and it comes down to just ONE thing:

Don’t hold back communicating your love, appreciation and gratitude to just one day a year.

Professional Situation: Don’t “save up” all your communication or attention until you want something from a client or contact.

Professional Solution: Business relationships should be nurtured and cultivated all the time, not just when it’s time for more money. Find ways to reach out and contact not just your current customers (or employer) but your extended network “just because.” How do you do this? LinkedIn, yes. But I’ve found a better way.

Try keeping professionally connected by using a great program I’ve found called Contactually. Find an article about your local Double-A sports team you know the woman you met last spring at a business mixer would love? Email it to her. Send it to her via Twitter. Remind her that you 1) still exist 2) remember her and 3) value keeping in touch even when it’s not with your hand out.

Have top A-Lister contacts you need to make sure you stay top of mind with even if you aren’t currently working with them? Take a peek at the calendar reminder list in the personal section below for some ideas. While I’m NOT suggesting you send a sexy note to a business contact, I am suggesting you think about reaching out above and beyond digital communication. Need ideas? How about:

  1. Sending a fruit or snack basket to your contact and their TEAM
  2. Offering up a set of sport or entertainment tickets
  3. Making a donation to an organization they support in their name
  4. Writing an old-fashioned hand written note and put a real stamp on it
  5. Taking them – including their partner or spouse – to dinner

Need more pointers on how to properly grow and feed your network? Check out Jessica Levin’s new book (aptly for sale on Valentine’s Day) Perfect Pairings: The Art of Connecting People. Above all else, give to others first without expecting anything in return. Ever.

Personal Situation: Giving flowers, candy or presents (or saying “I love you”) ONLY on Valentine’s Day.

Personal Solution: In my opinion this could be construed as “forced appreciation.” You run the risk of the recipient feeling that you are ONLY participating because the Hallmark and Kay Jewelers commercials say you HAVE to. It’s really no way to grow and thrive in a relationship. Of course there are plenty of ways to show you care for someone OTHER than flowers and gifts. The point here is that if your partner desires and appreciates these things (such as an occasional bouquet of flowers or an unexpected “I love you”) then you need to find a way to do it.

What if your partner IS the type of person that appreciates random tokens and reminders of your affection (and there is NOTHING wrong with wanting someone to treat you this way, I will have no shaming here thank-you-very-much) and you are about as excited to do this as stripping wallpaper? How do you meet in the middle?

First, set a recurring reminder in your calendar for an odd number of days, say 11 or 19 or 29 or 41, so it doesn’t appear completely calculated (like the first of every month or every other Friday.) In that calendar reminder keep a list of  ‘spontaneous’ events like:

  1. Sending flowers (not just roses)
  2. Texting sweet emoji-filled messages
  3. Planning a ‘date-in’ night (a great sci-fi movie, a bottle of red and a cheese plate that takes up the largest serving platter I own is top on my list)
  4. Hiding a steamily-worded sticky note where only they will find it
  5. Planning a weekend getaway that you can choose from

The idea is to break out of the routine of saying “I love you….can you put away the laundry” or “it’s the third Friday of the month, I guess we should go out.” If your partner absolutely HATES the idea of any of these things then I would assume (or HOPE) that you would take that to heart. Not everyone wants or appreciates physical gifts, but I’m pretty confident that everyone wants to be made to feel loved and appreciated by the people they care about.

In my own experience I would rather receive nothing on Valentine’s Day than ONLY get those things on Valentine’s Day (it feels forced, and again, I’m still carrying a bit of guilt that if I deserved it I would receive it.)

Summary: Gift don’t have to cost anything. Real romance isn’t about giving – or receiving – gifts and it should not be “saved up” for or begrudgingly given on February 14th. Real business relationships aren’t about only calling on them when your hand is out. The effort counts, trust me.

Better yet, buy YOURSELF those things not only on Valentine’s Day (but really, I mean the day AFTER because it’s all on clearance) and all the times during the year you feel that you deserve or desire it. And professionally, ask for what you want and accept nothing less. If that means payment up front, or a raise, or acknowledgment – tell those you interact with what you want.

Hoping someone (professionally or personally) will figure out what you want is unrealistic to them and disappointing to you.

Don’t gauge your value on someone else’s ability to demonstrate appreciation to you. (Click to Tweet!)

For the record, I WISH I could fall head over heels in love with the idea of Valentine’s Day. While it would be great to get a few dozen roses, a massive box of candy and a weekend trip (dear heavens someplace WARM!) on February 14th, I would much rather get small tokens often throughout the year. I’m going to take my own advice and set a calendar reminder for every 16 days and do something amazing for myself… and that starts tomorrow when all the candy is on 80% clearance!