First, I have heard that it is wisdom to never leave a pastorate UNLESS you already have another pastorate to go to. It's just the truth of the matter that pastors that are just floating around without a church are often perceived as somehow damaged goods, when the truth might very well be that they are an exceptional fit. DO NOT expect another church to be so spiritual that they will be able to see through all the baggage and know that you are the right man.It is beyond question that we should have God's PEACE about leaving. I think the most pastors do NOT have a clear word from God to depart...however, I like to think that most have PEACE about leaving...and that is very important to have. When you are struggling, struggling, struggling, it MAY be a sign that it's time to leave...or it may be a sign that the devil is fighting because he sees victory on the horizon.I have seldom known of a pastor who LOVES pastoring his church, whose people love him, who is experiencing great success...wake up an feel that God wants him to leave. It happens, of course. But most of the time there are signals that it's time for a change for the pastors...and the church. A pastor sometimes has to own that he has taken a church as far as HE can (he may be worn out, he may have been placed there by God to somehow keep the lights on until the next man could get there, he may just know that he has taken them as far as he has the ability to take them). That's perfectly OK...even though it can hurt to see a church suddenly seem to spring to life when you leave. But God keeps His Own records. He knows when credit is due you for having borne the heavy load during the most trying times. I have noticed that some pastors, after a building program, leave. I think that PART of that is because it was a wearing and wearying process...and that now that it's done, another pastor can come in a help the church more than they weary pastor could (at the same time, that next pastor might have never been able to shoulder all the weight that the former one did).Now, if you mean RETIRE, I think there is a different set of markers....A pastor is often like a heavyweight boxing champion who refuses to retire because, so far, no one has sent him to the canvas. And, when he does finally get hurt, he thinks it was a fluke and will keep on going...until it happens again.It is RARE, I think, for a pastor to leave at the very top. He may leave NEAR the top, but typically I think the pastor has to realize that it's not working like before. It might be a drop-off in attendance that he is no longer willing to weather, etc. But that is a signal.Another is HEALTH. Sometimes, a pastor needs to step away from the pastorate precisely because the pressure can wreck one's health (as well as one's relationships with wife and family). Also, it's likely a good idea to step away in GOOD health. Why wait until you're a broken heap? Of course, ALL OF THIS is dependent on the peace and/or direction of God.Another is FINANCES. If the man is financially stable enough to leave, that helps the decision to be made. If he is NOT financially stable enough to leave, that can make it a challenge to pull the trigger. The parsonage, the utilities, and/or the salary being left behind can likely do more damage than staying, if the pastor is not prepared.Again, a retiring pastor often has to be knocked down a few times before he realizes that, hey, I can't spring back like I used to...I can't make a comeback like before. CONCERN ABOUT LEGACY often holds back pastors from retiring, I think. They hang on and on, trying to make a breakthrough (perhaps) or try to ensure that the right person follows them and keeps the church going. At some point, we have to leave it in the hands of the Lord. After all, if the Lord builds not the house.... And we have to trust HIM to somehow make it all work according to HIS plan. I imagine many pastors have been disappointed with how things all turned out after they left, but you can't fix that. I've known of pastors hand-selecting their successor...only to find out that they made a very poor choice. And I've known (and experienced) GOOD pastors that followed GOOD pastors, creating an ongoing legacy of that being a good church! (Thank the Lord for such men who come in continue to build upon a good foundation.)