How to Choose a Real Estate Brokerage in Chicago

The Complete Guide for Newly Licensed Brokers

Is Real Estate Right for You?

Before you choose a brokerage, answer a harder question: Should you become a real estate agent at all?

This isn't gatekeeping. It's protecting you from a costly mistake. The people who succeed share certain traits, circumstances, and tolerances. The people who wash out often lacked one or more of these from the start—and no brokerage can compensate for that.

Financial Stability

Do you have 6-12 months of living expenses saved, OR a working spouse/partner whose income covers household basics

Real estate is commission-only. You will likely earn nothing for 3-6 months. If financial pressure forces you to take any client, cut your commission to win business, or panic-pivot back to a salaried job, you won't survive long enough to build momentum.

If no: Consider building savings first, or starting part-time while employed elsewhere.

Can you invest $3,000-5,000 in your first year for licensing, fees, marketing, and operating costs—without expecting immediate return?

This is a business with startup costs. If spending money before making money creates anxiety that affects your daily mindset, you'll struggle.

Rejection Tolerance

Can you hear "no" 50 times and still make the 51st call with genuine enthusiasm?

You will be rejected constantly. People won't return calls. Leads will ghost. Deals will fall through. Friends will use another agent. This is normal, not failure. But if rejection spirals you emotionally, this career will be painful.

Are you comfortable asking people you know for business—directly, explicitly, repeatedly?

Your first clients will come from your existing relationships. If asking feels "salesy" or embarrassing, you'll avoid it. Agents who avoid asking don't get clients.

Schedule Reality

Can you work most Saturdays and many Sundays for the foreseeable future—without building resentment?

Buyers want to see homes on weekends. Sellers want open houses on weekends. If you have family obligations, hobbies, or a strong preference for weekends off, this will create ongoing conflict.

Are you able to take a call at 8pm on a Tuesday and handle it professionally?

Real estate doesn't respect business hours. A client's offer deadline doesn't wait until morning. If unpredictable hours will damage your health, relationships, or sanity, factor that in.

Personality Fit

Do you genuinely enjoy meeting new people and building relationships—not as a skill you can learn, but as something that energizes you?

Introverts can succeed in real estate, but it's harder. This job is constant human interaction. If a day full of conversations drains you completely, consider whether you want that as your daily reality.

Can you remain calm and solution-oriented when a transaction is falling apart and your client is panicking?

You'll be the steady hand in stressful situations. If you absorb others' anxiety rather than diffusing it, both you and your clients will suffer.

Support System

Do you have at least one person in your life who supports this career change and understands it may take 18-24 months to stabilize?

Unsupportive partners, skeptical family, or friends who constantly ask "so how's that real estate thing going?" create pressure that compounds the inherent difficulty.

The Honest Count

If you answered "no" or "I'm not sure" to three or more questions, real estate may not be the right fit—or not the right fit right now. That's not failure. That's useful information.

Consider waiting until finances stabilize, starting part-time while keeping other income, pursuing a salaried real estate role first, or exploring other careers.

If you answered honestly "yes" to most questions, you have the foundation for success. Now the brokerage choice actually matters.