diff --git a/cmd/root.go b/cmd/root.go
index a837216..50f06c3 100644
--- a/cmd/root.go
+++ b/cmd/root.go
@@ -65,6 +65,7 @@ func init() {
 	rootCmd.AddCommand(scaffoldCmd)
 	rootCmd.AddCommand(queryCmd)
 	rootCmd.AddCommand(analyzeCmd)
+	rootCmd.AddCommand(workonCmd)
 
 	// Add model flag to all commands
 	rootCmd.PersistentFlags().StringP("model", "m", "", "Grok model to use (overrides config)")
diff --git a/cmd/workon.go b/cmd/workon.go
new file mode 100644
index 0000000..f18a868
--- /dev/null
+++ b/cmd/workon.go
@@ -0,0 +1,40 @@
+package cmd
+
+import (
+	"fmt"
+
+	"github.com/spf13/cobra"
+
+	"gmgauthier.com/grokkit/internal/logger"
+	"gmgauthier.com/grokkit/internal/workon" // we'll create this next
+)
+
+var workonCmd = &cobra.Command{
+	Use:   "workon",
+	Short: "Start work on the next todo item from the queue",
+	Long: `workon picks the next .md file from todo/queued/,
+moves it to todo/doing/, creates a matching git branch,
+asks Grok to generate a Work Plan section,
+appends it to the file, and commits everything.
+
+Purely transactional — one command, clear success or failure.`,
+	RunE: func(cmd *cobra.Command, args []string) error {
+		if len(args) != 0 {
+			return fmt.Errorf("workon takes no arguments")
+		}
+
+		logger.Info("Starting workon transaction")
+
+		if err := workon.Run(); err != nil {
+			return fmt.Errorf("workon failed: %w", err)
+		}
+
+		logger.Info("Workon completed successfully")
+		return nil
+	},
+}
+
+func init() {
+	workonCmd.Flags().StringP("message", "m", "", "Custom commit message (default: \"Start working on <item>\")")
+	// -f and -c flags will be added later when the spec needs them
+}
diff --git a/internal/workon/workon.go b/internal/workon/workon.go
new file mode 100644
index 0000000..ae30094
--- /dev/null
+++ b/internal/workon/workon.go
@@ -0,0 +1,35 @@
+package workon
+
+import (
+	_ "gmgauthier.com/grokkit/internal/errors"
+	"gmgauthier.com/grokkit/internal/logger"
+	// TODO: import todo, git, grok packages as we build them
+)
+
+// Run executes the full workon transaction
+func Run() error {
+	logger.Info("Bootstrapping todo structure if needed...")
+
+	// TODO: todo.BootstrapIfMissing()
+
+	logger.Info("Selecting next queued item...")
+	// TODO: item, err := todo.NextQueued()
+	// if err != nil { return err }
+
+	logger.Info("Moving item to doing/ and creating branch...")
+	// TODO: branchName, err := todo.MoveToDoingAndCreateBranch(item)
+
+	logger.Info("Generating Work Plan via Grok...")
+	// TODO: plan, err := grok.GenerateWorkPlan(item)
+
+	logger.Info("Appending plan to todo file...")
+	// TODO: err = todo.AppendWorkPlan(item, plan)
+
+	logger.Info("Committing changes...")
+	// TODO: err = git.CommitWorkonChanges(branchName, item)
+
+	logger.Info("Optional post-steps (cnadd, open IDE)...")
+	// TODO: postSteps()
+
+	return nil
+}