This is a very good question and one that I believe every individual and family needs to work out for themselves. However, I hope that sharing how I approach this issue will give some questions for you to consider as you wrestle with the issue and make the decision for yourself.
You might be surprised to even learn there are options about when to celebrate. The calendar says when the holiday is so what is the problem? Well the problem is that the calendar was pre-set after the Jewish people went into diaspora (dispersion around the world) and the Biblical instructions for celebration are based on sighting the new moon in Israel each month. For some more black and white thinkers this creates a moral dilemma. Before modern times the moral dilemma was easier to address–we aren’t in Israel and we can’t see the moon there. In modern times, however, not only is Israel a Nation where many Jewish people are living and can report seeing the moon, but the internet provides the opportunity for the appointed appropriate people in Israel to post the sighting of the new moon and everyone to have that info fly to their cell phones and email accounts. It could even be posted on facebook! And, in fact, that is what some have opted to do.
I don’t think there is anything wrong with this approach. At the same time, I see very impractical issues here. For instance, Israel is 9 hours ahead of where I live. So do I begin my celebration of Rosh Hashanah when the new moon is sighted in Israel and stop what I’m doing around 8 or 9 in the morning and gather with everyone to corporately celebrate (because if we’re being sticklers for the instructions this is a corporate worship festival). Or do I wait until night fall which is 9 hours later than the original sighting in Israel which makes it still not the exact time that Scripture says we are to celebrate?
Even more important to me than seeking to engage in a literally accurate celebration is Yeshua’s admonition that love of God and our neighbor is to be our guide for whether or not we are approaching the instructions and commands in Torah with the right goal. While it’s true that our congregation isn’t currently engaged in hardcore outreach to the Jewish people, it is also true that a desire to teach all believers who are on the tree of Israel (whether grown there by birth or grafted in) to live in such a way that the Jewish person who has removed himself from the tree will desire to be grafted back in (see Paul’s Olive Tree teaching in Romans) means we have the current and local Jewish community in mind when we approach these decisions.
What I see in Scripture is that Yeshua was a Pharisee. And he upheld all of the tradition that wasn’t constructed in error of interpretation. Very often he told the people listening to him to do everything the Pharisees *said*–just to not live the way they were living because that wasn’t in agreement with their words. It was the Pharisee sect that had power in Yeshua’s day and in order to be recorded as reading in the Temple, and discussing the things he did wtih the people he did he would have had to be part of their sect. In fact, it was the Pharisees who held to the Resurrection of the Flesh and other things that the Torah teachers and scholars and rabbi’s questioned Yeshua about directly to see where he stood. Yeshua also told his disciples that they had the authority to interpret Torah and trust that He was guiding them in the interpretation–and that their interpretation was to be binding for all of the believers.
When Yeshua chastised the Pharisees it was in the area of creating obstacles for people wanting to get to God. It was for causing Torah living to be experienced as a burden. When it comes to asking people living in diaspora to celebrate the feasts and festivals according to the sighting of the New Moon in Israel I have three great concerns that weigh in.
1) While living in diaspora believers are in different communities and quite often not in a place to practically stop everything at 9am on an unplanned day to celebrate. Because many moadim are shabbats, or days of rest, it is important that they be able to set up time to take off of work or plan to not be in school. Corporate holy days require planning of time and location for everyone to be present–this is especially challenging for those communities who do not have a regular place for meeting. There are very often more instructions for how to properly celebrate a moed than just making sure the timing is right. There are foods that must be prepared, often in advance, and there are items for ritual that must be gathered. Using the current calendar that was set up for those living in diaspora allows those in diaspora to do these things and be ready for the celebration.
2) If one of the reasons for celebrating the moadim is to provoke the modern Jewish person who does not know their Messiah to envy so that they will want to be grafted back into the tree that they were always intended to be a part of, it creates an additional and unnecessary stumbling block to their acceptance of Messiah if the call for them to come and worship not only includes this new presentation of Messiah, but an insistence that their own worship of God has been on the wrong date and not done correct according to Scripture. It becomes, “You need to know Messiah . . . AND let me tell you how you’re doing everything wrong.” When I follow Yeshua’s instruction to take everything back to love this leaves me feeling there is much lacking.
and 3) I ask myself in most things what my motivation is for doing something how I’m doing it. Everything I read about observing the high holy days based on the sighting of the New Moon in Israel is focused on being “right” in our celebration. Please don’t hear what I’m saying as an argument for being wrong. What I’m saying is I don’t think that right and wrong are supposed to be our standard for concern. As I already mentioned, Yeshua himself said that love was to be our standard for whether we are properly interpreting things. And I go back every time I look at this issue to the instruction that timing everything based on the sighting of the New Moon in Israel is for “when you are in in the Land which the Lord will give you.” So if I were in Israel I would most assuredly take literal and serious the instruction for how we should time our celebration. And I would rally everyone around me to follow this instruction so that we could corporately experience the expectation of waiting and the ambiguity of the exact time and date would create excitement in me! While in am not in the Land, however, I am very comfortable with planning my celebration–my practice for the time to come when we will see and understand even better the reasons that we are called to practice these things each year and to learn from them each time we celebrate–around the calendar that is being used by everyone around the world who is anxiously awaiting the coming of Messiah (whether they understand it to be His first coming or, like us, His second).
As a last thought on this topic, in Yeshua’s day it was the Sadducees who were the group that held most tightly to the literal interpretation and application of what was in Scripture and rejected the oral tradition that helped interpret and apply these things. It would be the Sadducees today who would be arguing loudest for the celebration wherever you are of the High Holy Days to be celebrated according to the sighting of the New Moon in Israel–regardless of where you personally live. It was the Sadducees in Yeshua’s day who rejected the resurrection of the flesh and other things that Yeshua challenged them about. Yeshua did not come as a Sadducee. This doesn’t suggest to me that Yeshua loved them less–only that Yeshua was not as concerned with being literal and right in the way that we humans sometimes set as our personal goal.
Ultimately, though, as I said at the beginning, everyone needs to determine for themselves how they will approach this question and how they will answer it. I encourage you to embrace the dating that will best support your celebration of Messiah, your obedience to the commands and instruction of Torah, and your love for God and your neighbor. As you do these things, I pray that you will have a blessed and holy celebration!