Having been left to myself, for some days past, I have made use of the opportunity for bestowing on your letter of the 20th Ult: handed to me on the road, the attention which its important contents claimed.1 The questions which it presents for consideration are 1. at what time a notification of your purpose to retire will be most convenient. 2 what mode will be most eligible. 3 whether a valedictory address will be proper and adviseable. 4 if both,2 whether it would be more properly annexed to the notification, or postponed to your actual retirement.

The answer to the 1st question involves two points, first the expediency of delaying the notification; secondly the propriety of making it before the choice of electors takes place, that the people may make their choice with an eye to the circumstances under which the trust is to be executed. On the first point, the reasons for as much delay as possible are too obvious to need recital. The second, depending on the times fixed in the several States, which must be within thirty four days preceding the first Wednesday in December, requires that the notification should be in time to pervade every part of the Union by the beginning of November. Allowing six weeks for this purpose, the middle of September or perhaps a little earlier, would seem a convenient date for the act.

2. with regard to the mode, none better occurs than a simple publication in the newspapers. If it were proper to address it through the medium of the general Legislature, there will be no opportunity. Nor does the change of situation seem to admit a recurrence to the State Governments which were the channels used for the former valedictory address.3 A direct address to the people who are your only constituents, can be made I think most properly through the independent channel of the press, through which they are as a constituent body usually addressed.

3. on the third question I think there can be no doubt that such an address is rendered proper in itself by the peculiarity and importance of the circumstances which mark your situation; and adviseable, by the salutary and operative lessons of which it may be made the vehicle. The precedent at your military exit, might also subject an omission now to conjectures and interpretations which it would not be well to leave room for.

4. The remaining question is less easily decided. Advantages and objections lie on both sides of the alternative. The occasion on which you are necessarily addressing the people, evidently introduces most easily and most delicately any voluntary observations that are meditated. In another view a farewell address, before the final moment of departure, is liable to the appearance of being premature and awkward. On the opposite side of the alternative, however, a postponement will beget a dryness and an abridgment in the first address, little corresponding with the feelings which the occasion would naturally produce both in the author and the objects; and though not liable to the above objection, would require a resumption of the subject apparently more forced; and on which, the impressions having been anticipated & familiarised, and the public mind diverted perhaps to other scenes, a second address would be received with less sensibility and effect, than if incorporated with the impressions incident to the original one. It is possible too, that previous to the close of the term, circumstances might intervene in relation to public affairs or the succession to the Presidency, which would be more embarrassing, if existing at the time of a valedictory appeal to the public, than if subsequent to that delicate measure.

On the whole my judgment leans to the propriety of blending together the notifying and valedictory address; and the more so as the crisis which will terminate your public career may still afford an opportunity, if any intermediate contingency should call, for a supplement to your farewell observations. But as more correct views of the subject may produce a different result in your mind, I have endeavored to fit the draught inclosed to either determination. You will readily observe that in executing it I have aimed at that plainness & modesty of language which you had in view, and which indeed are so peculiarly becoming the character and the occasion; and that I have had little more to do, as to the matter, than to follow the just and comprehensive outline which you had sketched.4 I flatter myself however that in every thing which has depended on me, much improvement will be made, before so interesting a paper shall have taken its last form.

Having thus, Sir, complied with your wishes, by proceeding on a supposition that the idea of retiring from public life is to be carried into execution, I must now gratify my own by hoping that a reconsideration of the measure in all its circumstances and consequences, will have produced an acquiescence in one more sacrifice, severe as it may be, to the desires and interests of your country. I forbear to enter into the arguments which in my view plead for it; because it would be only repeating what I have already taken the liberty of fully explaining:5 But I could not conclude such a letter as the present without a repetition of my anxious wishes & hopes, that our country may not, in this important conjuncture be deprived of the inestimable advantage of having you at the head of its councils. With every sentiment of respect & affectionate attachment, I am, Dear Sir, your most Obedt freind & Servant