This is written on the letterhead of J.H.Zimmer Co., Long Island Real Estate, Farms and Water Front Property. James is trying to capture his life dilemma as methodically as he knows how. Would he turn into a back-slapping small-town Rotarian or simply a restless misfit? Or should he force his wings open and fly into the unknown future, independent of his family?

Postmarked Tuesday 6.29.26, from James in Lynbrook NY

June 28 night

This paper [the letterhead] strikes the tone of what this letter is to be — a business discussion. There is a possibility of choosing between alternatives in the near future, and I want to know your feelings on the subject.

First I will attempt to outline two pictures, as nearly impartially as I can, in form both narrative and descriptive — beginning with the nearer (no attempts at unity or order):

I. The alternative as per letterhead:

A. The Great God Real Estate.

1. Market is at present inordinately dull; may pick up in 3 weeks, 3 months, or 3 years.

2. None of the offices are doing much; our office nothing — we are newcomers to the field.

3. There is a fair prospect of developing a moderately lucrative business in two or three years time; this is a growing suburban section wherein real estate cannot remain long inactive.

4. My father is willing to pay me $25 a week plus half commissions, or half profits.

5. The work involves no very high order of intelligence; listings must be kept up to date, the geography of the section known, catchy advertisements written.

6. Theoretically, there is great room for ability to size up people and their wants; to be diplomatic; to play the game psychologically.

Let the link-sausage manufacturer and his rotund spouse from Brooklyn do their own sizing up.

7. Practically, the usual operation is pretty mechanical in 90% of transactions or attempted transactions; you spread your wares in the form of shiny new houses, all more or less alike, and let the link-sausage manufacturer and his rotund spouse from Brooklyn do their own sizing up; in rare instances clients come along with whom a certain amount of finesse and non-Babbitt jargon may be to advantage employed.

8. Success in this business is greatly enhanced by attendance at real estate dinners; by being a Rotarian and an Elk; by being a staunch citizen and ballyhooing ecstatically from the soft drinks booth at the Volunteer Fireman's Block-party.

B. A few advantages

1. More or less your own boss.

2. No commuting.

3. Your own time (little trips, days off, etc., etc., arrangeable most anytime).

4. Time for reading, for tennis, for a languid philosophical country life.

5. No commuting

6. Fair prospects for a quite pleasant little home in the woods pretty soon.

C. Future Prospects

1. Financially about as good as most businesses, which may not mean very good.

2. Subjective state: either subdued to being a platitudinous booster, a conventional small town business man, or if not so subdued, still a misfit as a good Realtor.

Summary

The Great God of Real Estate offers you the opportunity of becoming the wife of Mr. J.H.Zimmer, Real Estate and Insurance, Homes and Homesites 5 minutes from the station. No very adventurous business future; the greatest in intellectual matter we might have to discuss in re my business would be a speculation on a business lot or the prospects of making a given sale. Social, or friendship, value of business associates practically nil. Lots of time off; late morning rising; country life, tennis, a house in the trees and fresh air. Wife of a struggling real estate salesman for some years — Plenty of financial uncertainty, but deplorably little life uncertainty — not much gypsy spirit — an attempt to start at a not too high top rather than a start at a hard, discouraging bottom in something that smacks a little less of the auctioneer, the insurance man—

The Other Alternative: The Great Unknown, which is so seldom Great and not long Unknown.

1. This alternative looms much more vaguely; may be but a figment.

The Great Unknown, which is so seldom Great and not long Unknown

2. Involves an attempt to secure a job which may ultimately lead to a position, at best of only mild financial success and popular success, in which work, some brain action, and a general attempt at refinement and intelligence are business assets of more value than wind, steam, and speed.

3. Possibly reporting; possibly hack writing; possibly a sort of secretaryship to some man; possibly at the bottom in some publishing house; perhaps personnel work with a large company.

4. Low salary.

5. Few shows, few new hats, no entertainment, a one room apartment in not the most desirable section of the city for a year or so, then a suburban place & commuting. Pretty regular hours; Sat. PM's and Sundays the only time-off to be counted on.

6. Rather greater independence from Pater Zimmer; perhaps a psychological but certainly not a material advantage; Pater Zimmer is usually willing to advance aid of sundry sorts without taking credit unto himself for so doing.

7. A certain amount of pioneer spirit, as contrasted to the comparatively flabby policy of trying to fall into a business which is somewhat of a graft, rake-off, unearned increment sort when it is good, and a thankless, anxious, uncertain job when it is bad.

8. This option holds the chance of ultimately winding up in as sordid a trade as Option One; under stress of gnawing hunger and ill-shod progeny, you know, one is glad to spear a sinecure in the cloak-and-suit trade.

Conditions like this seem quite inevitable. By way of example, Archie, who was my roommate in Larkin's house first term of 1922-23: he graduated 3-1/2 yrs. ago and has been married 3 years; at present he finds himself unable to get a job paying more than $25 a week in his profession of engineering. Louis Roess, while rather better situated by virtue of having brains, is starting in as an instructor at $1200 or $1400 per year.

The other night Mrs. Beaman, a doctor's wife who was my S.S. teacher in days gone by, called on us; a delightful lady, has a son and daughter in college. I showed her your picture. She was so delighted that she started in at once making plans for me. She said that when she married, her first bureau consisted of a packing box with cloth nailed over the front of it. It seems to have had no cultural ill effects on her; rather the reverse.

Mr. Ebberts had to ask his boss to advance him two weeks pay ahead in order to finance bread and butter during his first week of married life.

All this by way of encouraging you for the objectively drab days that are coming to you.
But about these alternatives: ponder this unintelligible set of dilemma horns, and tell me what you think we should do — don't say "whichever you prefer," because I want but one thing — you under whatever circumstances you find most endurable.

This is a business letter, however, so I must fight down the things I want to say until anon.

Yours truly,
J.H.Zimmer
AT PRESENT

Don't allow time to elapse between your receipt of my letters and answering them — just write as often as circumstances permit