The IT Handbook
  1. 1Pick your pathSkirmish or Campaign
  2. 2Choose your classRoadmapsYou are here
  3. 3Learn your first spellsCheat sheets
  4. 4Train at campHome lab
  5. 5Face the trialInterviews
  6. 6Join the guildThe Friday newsletter
The Tavern Board · Roadmaps

Pick a path, then take the first step

Every path starts with the same fundamentals. Think of each as a class: the differences are where you spend your days.

Pay figures are U.S. national numbers from the Bureau of Labor Statistics. Your pay depends on where you live, the employer and your experience, so treat them as a guide.

Entry level

Help desk

Class: Healer · Fixes problems and keeps everyone working

Be the first person users call when something breaks. A suggested first 90 days:

  1. Weeks 1-4: Windows basics, ping, ipconfig
  2. Weeks 5-8: Active Directory user tasks
  3. Weeks 9-12: Ticketing and customer calls
Typical dayTickets, password resets, remote sessions
Pay$61,860 median
RangeUnder $41k to over $101k (10th to 90th percentile)
OutlookDown 3% from 2025 to 2035, with about 48,700 openings a year from turnover
Typical entrySome college courses, or a high school diploma with IT certifications such as CompTIA A+

U.S. user support specialists. Source: BLS, May 2025.

Step up

Systems administrator

Class: Warden · Guards the keep: servers, users and backups

Keep servers, users and backups healthy for one organization. A suggested first 90 days:

  1. Learn: Windows Server, Linux shell
  2. Learn: PowerShell, group policy
  3. Prove it: A home lab domain
Typical dayPatching, user accounts, scripts, monitoring
Pay$99,130 median
RangeUnder $63k to over $155k (10th to 90th percentile)
OutlookDown 4% from 2025 to 2035, with about 13,400 openings a year from turnover
Typical entryTypically a bachelor's degree in computer science or a related field, with no work experience required

U.S. network and computer systems administrators. Source: BLS, May 2025.

Fast learning

MSP technician

Class: Ranger · Travels between many realms: one team, many clients

Support many small businesses with one team and a shared toolset. A suggested first 90 days:

  1. Learn: RMM and PSA tools
  2. Learn: Microsoft 365 admin
  3. Prove it: Document a client setup
Typical dayMonitoring alerts, remote fixes, onsite visits
Pay$61,860 to $76,220 median
RangeUser support $61,860, network support $76,220
OutlookUser support down 3%, network support up 1%, 2025 to 2035
Typical entrySome college courses or an associate's degree, or a high school diploma with IT certifications

The government has no MSP category, so these are the closest U.S. job types. Source: BLS, May 2025.

Hands-on

Data center technician

Class: Artificer · Builds and tends the machines in the forge

Rack, cable and replace hardware in a facility. Many people reach this job from help desk. A suggested first 90 days:

  1. Learn: Hardware and cabling
  2. Learn: Power and cooling basics
  3. Prove it: Build and label a rack
Typical dayRacking, cabling, hardware swaps, monitoring server health
PayNo official figure
Typical entryEmployers often want about two years of hands-on server experience, and certifications such as CompTIA A+ and Server+

The government does not track this job separately. CompTIA's career guide cites a median of $70,500 but gives no year. Source: CompTIA career guide.