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So much of the energy around building Two Degrees has been focused on making the act of sharing with friends and family easier and frictionless.  With the genuine belief that people are kind, caring and willing to share what they have to enrich the lives of the people around them, we just wanted to make it easier to do.  And frankly, I wanted this to exist so that my wife, De Ann, and I could be more generous with our giving and sharing, without the logistical hassles that can accompany it.  In fact, in the early days we often said “If nothing else, we’ll build something that works for us to use!”

But I’ve found that generosity is a tricky trait.  It isn’t enough to always be the one sharing, or picking up the check, or doing kind things for people. I’m told that you have to allow people to show you kindness, to do nice things for you, and for you to be appreciative and gracious about receiving those gifts. I’ve struggled with this all my life and truth-be-told, it probably wouldn’t hurt to sit down with a therapist and dig into that for a bit.  But Two Degrees and the global pandemic have really gotten me thinking about this a lot in the last several years.  I’ve been doing a little self-help “research” (Googling) and some deep thinking, so I thought that it might be worth sharing it all with our community.  

I have to believe that there are others out there who feel the same way, so if you find yourself struggling with letting others do nice things for you, here are some things to consider.

You deserve it / you are worthy

This was a big one for me. Many people are givers because they don’t feel like they are worthy of having acquired the stuff that they have.  Or they don’t feel like they deserve to be the recipient of gifts, appreciation or generosity.  But you are.  Believe me you are.  One of the best articles that I came across on this topic was by Janice Pascual – you should read it!

Give the gift of good feeling that comes from sharing 

As a generous person, surely you know and like the feeling of appreciation that you receive when you share with others.  Why wouldn’t you want others to have a chance to feel that way by sharing with you?  If you must, consider it your “gift” to them to allow them to do things for you.  See what I did there…

Make sure that it is yours to give, or get permission in advance

An important consideration related to being generous with your time, money and stuff is making sure that you and your partner or those closest to you are in alignment with your efforts. If all you do is give away your time or your stuff to others, are you actually giving away stuff that doesn’t solely belong to you?  Are you actually stealing time from your family and relationships by being overly giving?  This ties into the next idea…

Keep it balanced

There is truth to the idea that you can be generous and give to a fault.  Always being the one to give or share can make the recipients feel uncomfortable and can create tension in relationships. Having balance is critical to fostering deep relationships, though it can be hard. My brother introduced me to an app called “Settle Up”, which has been great for keeping track of things when you are with a group while traveling or on an extended visit.  It keeps track transparently among all of the participants and makes it easy for everyone to know where they stand.  I know for me, I would rather be called generous than ever have someone think that I didn’t pay my fair share.  Apps like Settle Up, when used with well-meaning friends and family, can help alleviate the burden of keeping a mental score.  It is also a great reminder for when it might be your turn to pick up the check.  


I saved the best for last, because really this is what it is all about. When you have people in your life that you love and trust, you often feel an urge to show them by being generous with your time, gifts and experiences. But just as there is not a single love language, there are many different ways that people receive and reciprocate appreciation. The closer you are to a person, the more likely it is that you already know what they need and when they need it. But for others, it is often difficult to know, which is why communication is so critical.  Say please and thank you.  Be genuine.  Let people know what you need, and how they can reciprocate your generosity.  There’s a great article about this here if you want to dive in further.

At Two Degrees, we’ve built in a lot of these concepts into the application because we think that it is important.  Our hosts can specifically list how you can best show appreciation for their generosity.  They can also lay out some expectations in advance like, How long is “too long” before you overstay your welcome? What availability can you expect of me as your host? We like to say we make difficult or awkward conversations easy, or better yet, disappear. Clear expectations make for great experiences.

Share early and often.  Safe travels.  And don’t forget to let them return the favor.